Find cheap flights from Chicago to Caribbean

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CHI — Caribbean
Feb 17 — Feb 241
Round-trip
1 adult
Economy
0 bags
From?
To?
Thu 2/17
Thu 2/24

Good to know

Low season

August

High season

December

Cheapest flight

$48

Average price round-trip

$437

Good deal round-trip

$173

Good deal one-way

$99
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago O'Hare Intl to Saint Thomas Island Cyril E King
(avg. price over the last 2 weeks)
or less
or less

Top tips for finding cheap flights to Caribbean

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November and December. The cheapest month to fly to Caribbean is August.
  • Morning departure is around 21% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Caribbean flights

Top 5 airlines serving from Chicago to Caribbean

Scores according to KAYAK customer reviews
8.1
JetBlueOverall score based on 19966 reviews
8.3Boarding
8.2Comfort
8.6Crew
7.9Entertainment
7.8Food
Airline reviews
Cons: "No wifi or TV."
Read more about JetBlue
Cons: "No wifi or TV."
Cons: "Coffee was super week No movies ORD-JFK"
Cons: "Tv dont work in a fly of 4hr 30 min"
Cons: "This flight was very delayed"
Pros: "JetBlue it have a lot more space for your and it was on time too but this morning the rain delay us a bit because they close one of the run way so it was not easy to get out"
Pros: "The crew was good, and they tried to make up for the delay with a gift certificate"
Cons: "More than three hours of delay because there was no crew assigned to that flight"
Cons: "Everything could have been better. Flight delayed 3 hours due to JetBlue schedule mismanagement. No consideration for elderly when we had to change gates across airport. Poor communication on flight updates. And then as a perk to make up for delays, tried to sell us a credit card. Just Awful."
Pros: "The seats were great! Loved the legroom!"
Cons: "There were a lot of old movies in the selection."
Cons: "The food can be better."
Pros: "Loved the roomy seats"
Cons: "Sound system was low quality. Hard to here the movie."
Pros: "Unbelievable for the price."
Cons: "Nothing bad to say."
Cons: "Left very late because of delayed inbound flight and need for deicing."
Pros: "The baggage took an hour and a half to come off the plane. Very poor!"
Cons: "Chris Wolfe"
Pros: "The rescheduling of my flight via a phone call"
Cons: "The delay of course"
Cons: "My first flight was delayed an hour due to pilot error (we left the gate on time, but sat on the tarmac for an hour). This caused me to miss my connecting flight, which stranded me at JFK because they only had one flight per day to my destination. JetBlue's customer service told me I could not reach my destination until the next day, which was unacceptable (I had a morning interview). In fact, the only thing they said they could do was *PARTIALLY* refund my ticket, even though they stranded me in a completely different city. They also said I would "be able to" book a new flight with a different carrier, which cost roughly $400, using my own money. In the end, I spent about an hour talking with customer service until they were "nice enough" to do a partial refund with an additional credit equaling the remainder of my $400 ticket to fly with them in the future. It was still a very poor interaction with customer service."
Pros: "Clean plane"
Cons: "Took 3+ hours to get in the plane"
Pros: "Pilot’s smooth take off and landing."
Cons: "The weather haha."
Pros: "It was a great trip for the cost."
Cons: "Nothing."
Pros: "Free WiFi. Cute vids for Holloween"
Cons: "Nothing!"
Pros: "I liked that the pilot was able to make up some time because our flight was delayed over one hour in Chicago."
Cons: "The notification that the flight was boarding early. I enabled notifications and still did not receive notification that the plane was boarding."
Pros: "Flight was delayed 30 minutes at takeoff but landed when it was scheduled, so it was fine. Flight attendants didn’t make you stay in your seat, so you could use the lavatory. A fine, uneventful flight. Free WiFi. Snacks. Drinks. Fairly comfortable seats with decent legroom."
Cons: "Wish the seats in front of the emergency exit reclined."
Pros: "The crew was unfailing cheerful and helpful. The seats are comfortable and there’s a little more space than some airlines. The fight and particularly the landing was very smooth. Great experience!"
Pros: "crew was supportive. wifi in the flight"
Cons: "the wait time and the boarding, off boarding of the flight. No electricity in the aircraft."
Pros: "Nothing!"
Cons: "IT WAS TWO BOURS LATE!"
Pros: "This flight is 3 + hours delayed, and I think it’s because Jet Blue didn’t have a full flight for the 8:30 am departure, this is unacceptable and I need to be compensated for my time Winston White"
Cons: "This flight is 3 + hours delayed, and I think it’s because Jet Blue didn’t have a full flight for the 8:30 am departure, this is unacceptable and I need to be compensated for my time Winston White"
Pros: "The crew talked a big game. They were ready for anything, including loss of cabin pressure, paid snacks, and even a water landing."
Cons: "No water landing! I was excited to float around on a hot day, go down an awesome slide, and catch some sick waves, but come on people, we never even got a chance!"
Cons: "could not make it in time. Then we got on plane and pilot said it was an electrical problem on the flight but the generators were now up and at em again. Very hair raising ride for me - got in at 2:30 am with another hour to drive home - and I lost a LOT of confidence which I have always had in Jet Blue. I hope this is not the future we can expect with you"
Pros: "How easy it was to board"
Cons: "When I asked if there was any chance I could sit with my family they were nice enough to change are setting. Just a thought if the setting is random when you check in for your flight somewhere the computer should at least work with putting the last names together just a thought."
Pros: "The crews were very friendly A lot of options from direct tv and other entertainment programs The seats were wide enough Free Wifi"
Cons: "The plane got 2 hours delayed The screen was too small There was no charger on the plane Food option was limited"
Pros: "Entertainment, food, crew, and cleanliness were 100000% on point. Loved it."
Cons: "Turbulence and the flight was longer than necessary because we had to go around bad weather. Not the fault of JetBlue!"
Pros: "Easy boarding, friendly staff, nice choice of snacks and beverages. The JetBlue app is very useful."
Cons: "My in flight entertainment never worked. All I had available to look at was the JetBlue commercial channel showing me all of the entertainment I wasn’t able to watch. Not even the live view map worked. One of the attendants said something about resetting the system but I didn’t notice a change. I said something to one of the attendants a little later and she tried doing a reset again, but still no success. I could see other screens working fine and people were watching various programs while I just stared at a static map of the continental United States. Oh well, at least I was able to stream Netflix because of the free inflight WiFi."
Pros: "Good snacks, entertainment and excellent WiFi. Boarding was efficient and seats were comfortable."
Cons: "We arrived later for almost 2 hours"
Pros: "Per usual crew and plan itself were nice"
Cons: "Flight was delayed about 3 hours from scheduled take off"
Cons: "The flight did not have enough headphones for in-flight movies. Our tv screens also did not work well."
Pros: "Space seating"
Cons: "Same movies going and coming back."
Cons: "my flight was delayed for 2 hours and there was no compensation for it"
Pros: "Our flight attendant Jeramy was FABULOUS!!"
Cons: "No movies just Direct TV."
Pros: "No gate, waited 2 hours in plane"
Cons: "When I scanned my boarding pass the Jetblue staff member told me my carry on was too big and had to be checked. This was puzzling to me because I travel often and do not have a problem with that bag. As I was sitting on the plane I saw everyone's bag's were bigger especially the man next to me. His was significantly larger and he had a large duffle bag between his legs causing him to manspread into my area. and yet i was told "make sure your purse is under the seat" seriously?! What about his giant duffle bag and huge carry on roller?!"
Cons: "Turbulence was terrible, understand that is not JetBlue issue - wanted to note."
Pros: "The crew was friendly."
Cons: "The boarding policy changes are confusing. No longer boarding from the rear of the plane and no explanation of how to board sooner without buying an extra space seat. Also the seats are less comfortable."
Pros: "You took great care of my wife who needed a wheelchair. the flight itself was delayed due to weather. I totally understand. I love the extra legroom"
Cons: "Movies didn't work and we were one hour delayed on the runway."
Pros: "The only good things about this flight were: - The crew at the gate were very friendly and attentive - We arrived safely without incident"
Cons: "We were delayed 2 times before boarding. We were delayed 1 more time while on the plane. The pilot told us there was equipment trouble that had been fixed, but there was paperwork to fill out and it would only be a few minutes...and then radio silence for 30 minutes before pulling back. The flight attendants rushed through the pre-flight announcents and I could only understand about 60% of it due to speed, volume and accent. Despite asking me for my drink order, it never came...and I only heard a few soda cans pop open at all. Did they just decide not to serve us? She even gave me a napkin for it. Luckily when they put the snack basket in front of me, there was a tiny bottle of water, which I grabbed...little did I know, that was all I would get. The flight attendants were just tapping in the back of the plane the rest of the flight. They didn’t even bother collecting garbage until we were on final approach. They also never did the normal checks before landing."
Cons: "flight was delayed 2 hours :("
Pros: "Crew was happy and friendly"
Cons: "Can’t think of anything"
Pros: "They refund me the money"
Cons: "I almost lost my international connection, had to pay double to get my destination on time"
Pros: "Friendly staff and the on board entertainment and snacks"
Cons: "The last time I took JetBlue the flight was delayed by almost 3 hours"

O liked the entertainment. I didn’t like being so close to other passengers, especially when they wore their masks wrong or took them down.

The best was the timeliness from JFK to SJU, and the comfortless of the Business Class seats. The worse is their poor choices of meals and beverages (Plate of Quinoa or a plate of Charcuterie). The should put more attention to those details, maybe even give something more generic that most people will love.

very good

Felt safe. No bathroom lines since many toilets are located throughout the plane. Passengers did great at following the rules.

Pros: "Excellent crew."
Cons: "Gate agents were a little snippy."
Pros: "The crew was amazing. But there were to many people on the flight for what’s going on. There were middle seats sold and people were upset."
Pros: "Mal servicio; compre un tickets que no permitía escoger los asientos y nos seleccionó la última fila en cada vuelo. La diferencia entre ser priority y regula es bien marcada"
Cons: "Mejor trato a todo pasajero; se reconoce las ventajas de estar en primera clase pero el servicio debe ser excelente"
Pros: "The crew was not overly friendly"
Pros: "Comfortable seats, nice staff, clean facilities"
Cons: "Nothing"
Pros: "Movies"
Cons: "Comfort. Jetblue offers betwee seats ne apacing betqeen rows"
Pros: "Great crew"
Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."
Pros: "Nice service"
Pros: "Love it"
Cons: "In the last months I have travel 3 times , this is the first with Delta. I can say it has been the best experience I had. Good entertainment, the access to texting and the variety of snacks make superior this airline."
Pros: "Crew was awesome. Very friendly."
Cons: "I’m 6 foot tall and I found my seat space feeling crowded. I found myself wishing for just 2 more inches of legroom. It feels that airplanes are being built for quantity of passengers, not quality of flight."
Pros: "Crew was very fast but not enough during boarding and people had brought oversized carry on luggage to the gate requiring stowing. We had checked a carry-on at check in and paid $30 while several people got theirs stowed for free which seemed unfair."
Cons: "The charging for checked luggage has created a situation that was unfair for all travellers and ultimately made the plane’s departure late. This policy drives people to bring too much luggage into the cabin, putting at risk the safety of others and delays."
Pros: "The friendliness of the passengers and most of the crew."
Cons: "One of the younger female flight attendants was rude . She was collecting trash and took my neighbor’s (aisle seat) trash but wouldn’t take mine. I tapped her elbow to show that I had trash, she looked at me but didn’t take it. She returned and still refused until I exclaimed. She rolled her eyes."
Cons: "Cabin was cold enough to store meat. Entertainment system was poor at best. And, of course, the seats were too small and uncomfortable. Time to start looking at other airlines."
Pros: "Friendly crew"
Cons: "No food was served"
Cons: "At least one hour late"
Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."
Cons: "I was flying standby. I checked the list on line and my name was number 5. I get to the gate and there’s just a handful of customers. The agent said there was enough seats for the standbys I wait and wait for my name to be called but no luck. My name wasn’t cleared yet. Finally I was the next to last one to get a seat. The gate agent who didn’t ask for my name tells me I was all the down at the bottom of the list. While I am glad that I got on I wish I knew what method is use to get your name on the stand by list?"
Cons: "Cabin was too hot since the very beginning. Even in first class."
Pros: "The counter assistant change my seats and my wife and me seat together"
Cons: "Hot cabin"
Pros: "Although our flight was fully booked. The crewmembers on this flight was professional, friendly and efficient. We boarded quickly and took off on time. We even arrived ahead of schedule. Each passenger was given free headphones and complimentary beverages and snacks. I love Delta they are a cut above the rest. They are constantly striving to put the customers needs and wants top priority"
Cons: "Tight seats need more legroom"
Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."
Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"
Pros: "Arrived early. Got a beverage & snack which is becoming rarer with American carriers. Video selection was very good. Staff was nice and attentive. Overall a good flight at a reasonable price."
Cons: "Narrow corridor to seats"
Pros: "Everything escept the seat that was too small. I also had problems with the entertainment when trying to see movies."
Cons: "Seats too small ant could not watch Movies beacause the screen was defective."
Cons: "Flight was delayed over 1hr."
Pros: "Buen entretenimiento."
Cons: "La incomodidad de los asientos además que la escala fue de más de 6 horas y fuimos los últimos en abordar. Para colmo los asientos fueron los últimos de la fila y ni siquiera eran reclinables. Creo que deben tomar en consideración a las personas que estamos tantas horas en la escala y permitirles abordar primero además de darles asientos más cómodos más aún si hemos comprado los boletos con tanto tiempo de anticipación."
Pros: "Giid free sandwixh. Very good entertainment system. Good seats."
Pros: "Well, the seats and the lavatories are smaller than ever. And I am quite petite."
Pros: "Excelente"
Pros: "Entertainment is very good"
Cons: "Send my carry on bag, outside."
Pros: "Late delay notification"
Cons: "Called the airline directly to verify the status of flight within 24hrs and everything was on schedule according to them. Even tho the airport at San Juan have not night arrivals due to the effects of Hurricane Maria, and on previous days the same flight had been moved to a morning schedule for that reason. I was notified of the delay within hours of departure of the connecting flight."
Cons: "Small plane"
Pros: "The flight left on time and we got in 15 minutes before the scheduled time. Awesome service from gate to gate."
Cons: "I didn't like that I had to pay for my bags and still purchase food on plane. The price for ticket is already overpriced to begin with. Fuel is cheaper, the planes burn less fuel due to updated design and still the tickets are three times the cost of five years ago. No one should have to pay for bags period. Show that you really care."
Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."
Pros: "Movie selection"
Pros: "Comfortable seating and clean interior. Flight attendants are helpful and courteous."
Cons: "Flight takeoff delayed one hour. Boarding has zoning, but with no structural boarding process, resulted some later zoning customers blocking earlier zoning customers in a single line. Suggest using multiple labeled queue lines, like southwest."
Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."
Pros: "Food was OK. Crew was very friendly"
Cons: "No Entertainment for a 4 hour flight. Plane was very old."
Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."
Pros: "Although I am a vegetarian, It was nice Delta was serving sandwiches."
Pros: "newer aircraft; good entertainment options; large overhead storage compartments"
Cons: "cramped passenger space"
Pros: "Excellent choices for entertainment in the 737-900ER. 110V AC and USB ports at each seat, lots of choices for movies and games on seatback screen. Free sandwiches handed out on board."
Cons: "Intercom didn't work super well. JFK is a terrible airport for connections."
Pros: "The plane,plane, plane! Very new and clean , good entertainment. Love it"
Cons: "People taking their time to put their luggage in the bin... Very annoying."
Pros: "Westjet crew are always amazing"
Cons: "Nothing."
Cons: "Everything was great. Westjet is so much better than Air Canada!"
Pros: "Everyone was friendly and efficient."
Cons: "Need to use your own device for entertainment, no screens in flight."
Pros: "Left early and arrived early"
Cons: "Cabin was way too warm. Also not as much space on 737-700 as 737-800"
Cons: "The flight was delayed for over 2 hours without explanation or apology. The entertainment system did not work on my computer. Either the system was not working properly and/or the troubleshooting instructions were incorrect. This was a five hour flight with no entertainment, in a cramped seat."
Pros: "The crew was efficient, but not like some WestJet flight attendants where they crack jokes, & make everyone feel glad they were on that flight."
Cons: "The pilot was going too fast on taxiing to the runway (trying to catch up from a ground delay), & nearly overshot the runway. Had to stop very suddenly and make a sharp turn. Not a great way to begin a flight"
Pros: "Good seat exit row"
Cons: "Flight did not leave on time and no updates"
Cons: "Sat in Plus. Horrible service. No hot towels. Had to ask for 2nd drink and was refused a coffee and Baileys with at least an hour left in flight. No snacks offered or served. The attendant spent most of her flight hiding in her seat and reading a novel. Brutal!"
Pros: "The crew was ok and the service acceptable"
Cons: "The got us a terminal in Toronto (for connection flight to Montreal) which took us 1 hr and 10 mins to switch. It is Air Canada which is sabotaging this good airlline. Is it unacceptable and Air Canada Rouge service is worst. Never fly ever again with Air Canada. I will give another chance to WestJ"
Cons: "Food options are terrible especially when you pay for them. Better quality needed"
Cons: "No beverage service at all and only pretzels offered when I asked if I could have nuts or cookies."
Pros: "The crew filled up my reusable cup instead of using a single use one for my drink. They were very friendly and great."
Cons: "A lot of single use plastics are used on the flight for food and such. It is very wasteful. It would be great is WestJet could find a way to lessen their plastic foot print"
Pros: "Great flight! Great service and way more room than air canada! And ACTUALLY on time!"
Pros: "Staff is friendly."
Cons: "We didn’t appreciate the walk from Gate 4 to Gate 41 TWICE when the departure gate was changed. We are in our 80’s and it was quite a trek!"
Pros: "The flight was on time."
Cons: "That I had to pay $30 for one checked bag, would have thought the first one was free!"
Cons: "Coffe was soooo bad!"
Pros: "Flight attendants, movie on board, price"
Cons: "Plane was delayed and the baggage handlers in Denver were Atrocious!! I actually took video I was so shocked!"
Pros: "One thing that was thoroughly entertaining and unique was magic mory our flight attendant. She was brilliant and fun making jokes or comments when she made announcements. I have never heard anyone like that before and loved it. It was no like the nonchalant speaking that no one wants to listen to because they’ve heard it so many times before. When Magic Mory spoke, she made sure she was entertaining us, cared cause she knows we listened to it who knows how many times. Thanks for the authentic experience on west jet Magic Mory! I personally love how she also made a little song dedication and sung over the intercom. Thanks for a memory experience!!"
Pros: "On time both sides"
Pros: "The check in staff are very helpful and kind especially Rachel! The service was excellent very happy and helpful staff during our flight. The pilots made such a smooth landing and we are so thankful to be home safely!"
Cons: "Still cramped in the seats!"
Pros: "Loved WestJet! They are the best airline, always super friendly"
Pros: "In the flight there was a crew member she was not polite ...As I want to use washroom urgently & I was not very much familiar where is washroom I asked her three times she did not reply back...Just walk away...if she does not understand me, she cam say pardon me...but she just left"
Cons: "Everything else was good...great help from Abbotsford staff...I really appreciate that"
Cons: "The wifi is paid.. no TVs"
Cons: "Did not purchase food on the plane"
Pros: "Agreed to check bag at gate, early boarding in return. Great gift!"
Cons: "LaGuardia is terrible. They shrank departure lanes and we got stuck on the plane for an hour. I hate this airport. Something always goes wrong."
Cons: "We didn’t like having to take the red eye to meet our Costa Rica connection. We"
Cons: "The flight from Toronto to Phoenix was even worse than Air Canada. No food available to purchase. Cramped seating. Entertainment system was difficult to navigate...the buttons didn't work half the time, the movies were already playing and all the "bad" words were edited out which changed the entire movie. Waste of time. Would not fly WestJet again based on this experience. And what's the point of checking in online when you're called to verify id again at the check in counter."
Cons: "Flight crew arrived late delaying take off"
Pros: "Arrived early"
Cons: "Seating in the back"
Pros: "Always friendly"
Cons: "No complimentary drink all of a sudden"
Pros: "Staff are always fun and efficient, but the drinks came very late. In Asia, even if the flight is only 1 hour, they have the time to serve a lunch and clean up....."
Cons: "Meal"
Pros: "Nice flight crew."
Cons: "Ground crew couldn’t get luggage on plane fast enough because of lack of staff so we sat on tarmac for 2 hours."
Pros: "Boarding was quick and the staff as very friendly. The pilot was hilarious."
Pros: "It was a smaller aircraft and the staff were friendly"
Cons: "was right at the back of the plane and could not hear the announcements clearly."
Pros: "The crew was friendly and attentive. Boarding was seamless and smooth. Departing from New York, they proactively asked the passenger to volunteer checking their carry-ons ahead of boarding so they didn't have to waste time when boarding the flight."
Cons: "There was no entertainment. The snack could have been something more substantial. The overhead cabin space both for departing Toronto and departing New York was was insufficient."
Pros: "Ease to board, on time boarding"
Cons: "Return to gate prior to take off"
Pros: "Great experience...."
Cons: "There were wait times...too long"
Pros: "We arrived early."
Cons: "Checked bag fees. Agents at check-in tried to get me to check my carry-on claiming my carry-on was too big. My carry-on is a pilot crew bag by TravelPro, which I pointed out to them. Had to get a supervisor. No free food during the flight. Luckily, someone told me. I ended up purchasing food from a restaurant in the terminal to bring on the flight."
Pros: "Very cheerful and friendly crew. Made the journey very enjoyable."
Cons: "Nothing"
Pros: "The staff were very good jumped in by running with me in a wheelchair till we met up with a cart then next team met up and took me again in a wheelchair down elevator made it just on time"
Cons: "Not having my rides there’s that I set up and almost late"
Cons: "Flight was delayed and they never let us onboard even when I was able to make it to the gate before it was closed. After missing the flight the hotel vouchers was provided but we were asked to report in 2 hours (i.e 4AM) so think abou whole night was literally wasted. Finally next flight was 11AM in the morning which I ended up boarding and finally reach Toronto after 8 hours of delay."
Cons: "Il serait bien d'avertir plus à l'avance les passagers au sujet de l'application nécessaire pour l'entertainement ou permettre de l télécharger via le wifi de westjet"
Pros: "A bit more seat room. I'm a tall guy and was a bit cramp"
Pros: "Westjet flight crews are always really nice and helpful. When we travelled out to kelowna on the 14th it was a day after our daughters 1st birthday and they announced it over the intercom which was sweet"
Cons: "The flight back was an hour late to begin with, flight itself was good landing was probably the worst landing I've ever felt in my 20-25 flights, was an extremely tough landing. Smoke alarms went off in he airport so we had to wait for a bridge and luggage"
Pros: "westjet connect to watch a tv show or the news or something"
Pros: "Great crew, West jet connect worked fabulously"
Cons: "Cramped space and airplane food"
Cons: "No entertain system"
Pros: "My daughter ordered the tickets for us but she didn't pick seats. We forget to pre checked in, either. Our flight was very full so We are so lucky got the first class seats! This is the first time in our life with first class experiences! It was on the July 4th and saw a lots of fireworks in the airplane! We are so exciting! Thank you for West Jet Airline!"
Pros: "Friendly staff"

I need to go back to waterloo this week

Horrible scam. Make you pay extra for more leg room then switch your seat as you’re boarding to a regular seat. Never fly American!

From the moment I walked into the airport in Chicago to the moment I was walking off the plane in Florida I had an unforgettable experience! I was traveling with my 3 month old by myself and everyone just made sure I was taken care of. I couldn’t thank them enough!

There was no entertainment and again, the seats were very cramped and uncomfortable.

I left my phone in seat 6C or B where I sat with my husband. The lady with the oxygen tank needed help coming back from the bathroom as we were ready to land. We stopped the movie we were watching on my phone to help her and I guess I forgot it. Please, please return my phone. Samsung note galaxy 20 ultra. It is on airplane mode. Thanks so much

While I can understand that the airline industry is a tough business, I did have a horrible experience with American Airlines. This will probably be my last time booking travel with this airline. To start, my first return flight on Sunday July 25th at 5:00 pm, AA 2779, had been delayed for more than six hours and the gate agents canceled our flight at the last minute. This problem occurred due to short staffing and the airline was unable to find a replacement co-pilot. As a result, I had to stay an extra night in Chicago and spend 120 dollars on a Lyft ride-share from the airport. However, I did manage to secure another flight during the following day, AA 4962, and I was happy to finally arrive home. Please take all of this into consideration and I would demand some compensation for the inconvenience.

Too busy trying to sell AA credit cards

This is a very short flight, so there actually wasn't any food or entertainment onboard. Although the pilot had warned of turbulence, the flight actually was quite smooth, especially compared to the VERY turbulent FAT-CHI leg we had just endured.

Pros: "I like American Airlines in general."
Cons: "I noticed there was a disagreement/issue between a passenger and the aircrew, but it was handled quickly when the passenger just left. I understand there are some issues sometimes, but I noticed attitude from three of the flight attendants during the flight. There were three teens in the back that kept rambling about how all planes have bombs, everyone there was turbulence we could go into a spiral, the plane engines could blow up, etc. It was clearly making passengers uncomfortable because they kept turning around and one lady even yelled at them. I'm honestly shocked the flight crew never said anything to them. I wasn't too worried, except that they ruined any chance to get some rest."
Pros: "Na"
Cons: "Did not make this flight"
Pros: "The crew was fine, friendly enough, although I was incredibly disappointed that they didn't force people to wear their masks as they boarded. They also didn't enforce masks over noses--rendering masks useless."
Cons: "The flight was completely full. And people weren't wearing masks as they boarded, and the flight attendants did nothing about that. Also, there was no distancing IN the airport during boarding. It's NOT DIFFICULT to put tape marks on the ground to ensure physical distancing. It is THEIR responsibility to make sure the process is safe, since half of the people seem to not care about distancing (or mask wearing). I'm incredibly disappointed and I will be flying Southwest for the time being: I hear they're better at enforcing distancing."
Pros: "The crew were wonderful and understanding and good sports."
Cons: "There were problems as soon as the plane got to the gate. After the passengers got off the plane, the man at the counter came on the P.A and said it’ll be a few minutes, they’re catering the plane now from the back to the front. The flight crew still needed to get on a preform safety checks. He apologized again. Then it was 8:40, time to take off and we’re still waiting to even board. The man at the counter said again, thank you for your patience and relayed the same message, only this time the flight attendants were walking away from the gate. Around 9 some lady higher up told the man to announce that the flight crew had timed out and stand by crew was on the way to the gate, said sorry again. A little later the man says sorry, there’s a gate change. You’re going to K6 now. When we get to the new gate it’s almost 9:30pm and while we were all gathered at the gate, the flight crew that supposedly “timed out” showed up and proceeded to get on the plane. Passengers started getting mad and saying we were lied to and to just tell us the truth. Chicago PD started showing up. We finally got on the plane but it would be another 30 minutes before we moved because of issues getting our bags off the original plane. We ended up being almost 2 hours delayed."
Pros: "The crew serving the plane didn't look like they wanted to be there. Somewhat abrasive. The entertainment was poor and not very easy to access through your mobile, Iphone and Ipad. If you want to provide a better customer experience, equip all your planes with seats video screens. Passengers on a 4 to 5 hours flight don't want to have to figure out what do to watch a movie or TV. I don't fly American that often, but wanted to give it a try to see the difference between you and the other airlines. I have to say that on the return segment (ORD to SFO), I was not that impressed."
Cons: "See above"
Pros: "The crew was fantastic and our seats were exit row which was comfortable. We had terrible weather and the pilots crafted an exceptional and safe landing. The flight attendant was hilarious!!"
Cons: "Nothing. It was great"
Pros: "Nothing"
Cons: "The cliff notes of this debacle are, inbound flight arrived late to Montreal, I contacted AA social media team to make sure they could notify the gate of my connecting flight, they didn’t after they said they did. Flight arrived in Chicago a little early, I have to wait 15 min for my bags from the valet, I run to the next gate and arrive with 13 min to spare, the gate agent (not nice) goes I’m sorry we already closed the door. I’m like, huh? Then he has the gall to tell me, “well had someone called us we could of held your seat”. That’s when I lost it. Needless to say I’m now flying to Dayton and back to Dallas. That’s in lieu of a 3:50 PM flight TOMORROW!"
Pros: "Everything."
Cons: "Waiting for 30 minutes a Dublin to dock."
Pros: "Outbound, it was on time, plenty of legroom, plenty of good snacks, drinks and food. An enjoyable flight. Score 10.0"
Cons: "Return flight - The flight departed 4 hours late. The seating was so cramped my husband couldn't move his legs at all, never mind try to sleep. The staff members were not smart in appearance, some with long untidy hair, and did not interact with passengers except to hand out food. The food was reasonable. We disembarked feeling like wrecks. Score 2.0"
Cons: "Our last 6 flights have all been changed or delayed significantly. Then they loose our bags on a direct flight. Won’t fly America airlines again!"
Cons: "This was my final connection from a long flight, we did a line to check in and get our boarding passes, when we got to the gate I found out I didn’t have a seat number asigned but husband did, they gave me one there but of course it was not next to my husband, it was the last seat available at the end next to restroom. The smell coming out from the it was so disgusting even before th first person went in, they should do something to improve the cleaness in the restroom between flights. It would probably take them 30 more minutes to do so, and I would not mind waiting for it even if this was my final flight after 15+ hours."
Cons: "The flight was delayed. The food was not great. There is not a lot of space in these planes, and it was a long flight. There is no power supply."
Pros: "Eventually, the actual flight was fine."
Cons: "Initially delayed by 3hours (mechanical) which was American Eagle couldn’t get their “bucket of bolts” to Springfield, MO on time so we missed our flight out of Charlotte to Barcelona. Then we were rerouted through Chicago, but lost our first class seats and were bumped back to coach. This was after I had bought first class tickets for the entire trip only to be told 3 months before leaving that AA decided to switch planes on our domestic flight so there’s were no first class seats. THEN, in Chicago we tried to get first class seats on British Airways which would have been fine but After being sent to another terminal (after the bus to that terminal had stopped running) we were turned back because British Airways wouldn’t accept the boarding pass that AA had issued us. Now, having to go back to the first terminal to DISCUSS all this, we miss that flight and wind up stuck in Chicago for another 24 hours. Then, that flight was delayed by 3 hours, so we lost a day and a half of our vacation."
Pros: "The lady at the counter before we boarded switched our seats for us so our tickets could be together."
Cons: "The seats we had were exit seats right next to the bathroom and it was a night time flight. So 8 hours overnight of constant commotion and people walking by. The flight attendants were blatantly rude and would sit right in front of us and openly talk badly about the passengers. One of the flight attendants walked by and literally just grabbed my drink out of my hand and took it. There was only one flight attendant who was actually pleasant and polite to everyone and her name was Kate. The other flight attendants were just rude and abrasive to everyone and basically would mock people who did not speak English as their primary language. We were both treated okay but I was truly appalled with the way they spoke to some of the other passengers."
Pros: "I liked getting to my destination on time."
Cons: "The one carry-on policy was silly and included personal items. I was told to repack my purse into my backpack which was already full. The boarding staff stood over me and told me to throw stuff away in my backpack and asked why I had packed certain things. I am in the process of moving back to the US from Korea after two years so everything I had was everything I owned in the world - which included some sentimental things like a stuffed animal from my mother who passed away when I was three years old. The most infuriating part of this however was realizing that there was one other bag in my overhead bin. In fact most of the overhead bins had one to two bags and plenty of room. My repacking and humiliation was unnecessary and it was only for the morbid satisfaction of the lady at boarding demanding it. At one point I heard her talking with her coworkers about “why couldn’t they freaking listen. We announced it three times.” Well I had approached the counter prior to arrival and they told me to get back in line when I tried to ask about my purse and backpack. In additional to the frustration of all of that, I received my checked in luggage with a wheel missing. I had just bought it and now I have to ship a wheel from the vendor in South Korea or buy new luggage. Thank you guys so much for letting me know which airline to never fly with again."
Pros: "I got here."
Cons: "Everything else. American cancelled my first flight from MSP to ORD. And when I got to Chicago, it cancelled my next flight to Nashville. The flight I managed to get on departed two hours late. There was no explanation for each of these cancellations/delays. There was virtually zero inclement weather anywhere, save for most of the country’s temperature being nearly equivalent to the surface of Neptune. And, the surly, clueless Chicago-based gate agent was the coupe de grace in my search for a reasonable explanation after which I waited impatiently for this episode to conclude. American get your act together."
Pros: "Nothing!"
Cons: "I was traveling today with my daughter, who is 6 months pregnant, my 3 1/2 & 18 month old grandsons, my husband & son-in law on an international flight from Chicago to Manchester. I was very disappointed a 757 was used for an international flight! No attempt was made by staff to accomodate our family with a extra seat for the infant, even though there were a large number of rows with empty middle seats (4 of which were directly behind them!) The 1st indication of the beginning of the NIGHTMARE was when the plane arrived in Chicago and overshot the gate, this caused almost an hour delay! (We heard our crew saying "oops" while looking out the window at the plane arriving & then again when they were discussing it would have been faster if the plane had used a different method to get to the gate again.) This was then followed by a mechanical problem with a frozen water valve, requiring us to be de-iced x2! Then we started to taxi out and again had to return because of a hydraulic problem that required repair. I think we were delayed almost 3.5 hours. The crew did bring a round of water during the onground delays, and offered free drinks later in the flight. The icing on the cake was not getting the stroller back at the gate because there were no baggage handlers. I can't tell you how much FUN that was trying to corral a toddler & 3yr old with all our carry-on bags while getting thru customs! Did I mention in our haste to get off that plane we overlooked my daughter's winter maternity coat in the overhead! May be time to switch to the Friendlier Skies of United for our UK travel!"
Cons: "American completely missed the mark. AA did not successfully change our reservation when the initial leg of our trip was delayed by an hour due to a fuel issue, which caused us to miss your connection in Chicago. Since American partners with Alaskan Airlines, American should have changed my reservations with regards to Alaska Airlines, but they failed to do that. I stood at the Alaskan Airlines counter as the plane left the gate with our empty seats because there was not a ticket. American Airlines did not change a reservation successfully and so although we had boarding passes with our names and seats and the flight number, the plane left without us. I was stranded and Seattle airport at midnight with a child and an infant with one diaper and one bottle left and it was a terrible experience with American Airlines. I do not recommend flying American they cannot get it together when problems happen with delays."
Pros: "The flight itself was fine"
Cons: "I bought the tickets together, but was informed at the ticket counter that i had only purchased tickets—not boarding passes. Boarding passes needed to be purchased by paying extra if my husband and I wanted to sit next to each other. I tried calling the customer service line through kayak and waited on hold for a long time with no indication of wait time. When the gate agent arrived, we asked and were moved to seats next to each other right away. The ticket agent at initial check in was very abrasive and non-solution oriented. if what she was saying was true— that we only paid for tickets and had to pay extra for boarding passes together— that was never made clear during the booking process. It’s unlikely I’ll use kayak again unless I know for sure what I’m buying."
Pros: "Nothing"
Cons: "I chose a package on the cheap flights that has a left hand side for choosing number of baggage which invariably inreases fare depending on the number of baggage and i choose 2 and paid for 2 baggage but the ticket came with 1 baggage and i contacted both by phone call, email and your website but did not get any fsvourable response. Had to pay again at the airport for the extra bag. This is highly unfair."
Pros: "The entertainment was good. Lots of choices. Food was about what I would expect for airline food."
Cons: "The seats were terrible. I don't know what it was about them, but I've never had a more uncomfortable flight. My husband had leg cramps for much of the flight and couldn't get comfortable. The rest of the flight was fine, but the uncomfortable seats were a huge minus. We'll probably try to avoid 787s from now on. The window-darkening system was annoying. They darkened the windows when it was dark outside and they darkened the cabin, so we couldn't look out the window. It was dark outside--why the need to darken the windows?? My husband requests window seats so he can look out the window."
Pros: "Flight was on time."
Cons: "The first plane was broken and the pilot kept coming to brief the passwngers that it was broken but it may be fixed and so on, it would have been better if he had just let the counter clerk say the plane is delayed due to maintenance. As a customer, i dont need all the rambling explanation every ten minutes about the issue. I was told that we could board another flight leaving in 30 minutes, so i went to that gate, crew was not there and we boarded the plane. We had to de- board and wait for the crew. After the crew showed up, the rest of the flight was pretty standard."
Pros: "Left on time, relatively comfortable considering I had already spent almost 9 hours on a previous flight, landed 30 minutes early"
Cons: "Mixed feelings about the entertainment app, I was pleased that something was available at all, however had the person sitting next to me not mentioned I needed an app to watch the in flight entertainment moments before it would have been too late to use the internet to download it, I would not have been able to use it, unless paying for a limited time package from AA to use the internet to download the app. A better job of advertising of the gogo app is needed more than the booklet in the seat pocket. Also I was only able to watch one movie, after that the system kicked me out saying high usage was making it not work for me. The gate changed a couple of times which had me trawling up and down the H and K concourses, could have done without that after the 9 hour journey I had already taken."
Pros: "*finally* getting rebooked"
Cons: "The aircraft was downgraded, so there were 12 "overbooked" seats. The flight was delayed several times, with each new delay only being acknowledged after the previous departure time had already passed. Eventually, the flight was "delayed" to 3:15, but then it was bumped BACK to 2:45, so one woman ended up missing the flight because she had gone to the lounge based on the 3:15 departure. I accepted a voucher, but as the original flight kept getting delayed and I couldn't receive the voucher until the doors closed, I almost missed the flight I was rebooked on. If airlines would just communicate better (e.g., tell us there's a delay *before the departure time has passed*), people would be much more willing to deal with the hassle."
Pros: "It was on time. Crew were very good."
Cons: "Plane seemed very dated. No individual entertainment No USB chargers Not much space"
Cons: "The airline "randomly" selected me for extra security. Even though I have TSA pre-check I was jostled around, sent to multiple security lines without any reasoning and the local Chicago TSA and airport staff didn't seem to know what to do. Once it was figured out I was subjected to what was essentially a cavity search. Again I HAVE TSA-pre-check but apparently that means nothing if an airline flags you. It was an extremely upsetting experience but you were in a situation of either agree to the invasive search or get stranded over 1000 miles from home. I will NEVER fly Iberia again after a cancelled flight and being stranded in the wrong country on the way to my vacation and the horrible security experience on the way back. I seriously may never go to Chicago either after seeing the complete lack of organization and traumatizing personal invasion. I fly a lot for work and have never had such a horrible experience. I would really like to know how many terrorists are caught with these invasive searches and would love to know the justification for sticking your hands inside someone's pants and grabbing their privates after they have already gone through a metal detector AND the body scanner. Especially for someone who has already passed a federal background check to obtain pre-check status. Absolutely ridiculous."
Pros: "Seats quite comfortable. Crew ok."
Cons: "Pitiful food offering and no entertainment at all when on previous 1.5 hour AA flight choice of movies."
Pros: "I have nothing good to say about the flight to LA or the flight back to Chicago from LA."
Cons: "3 of the 4 flights were late, and the 4th was canceled. The canceled flight was due to weather, but AA's response was to connect those of us stranded with a 3rd party vendor - Travelliance - with the promise of a SUBSTANTIAL discount for a hotel (SINCE THE NEXT FLIGHT I WAS GIVEN WAS 17 HOURS LATER!) - and there was, effectively, NO DISCOUNT. I have spent thousands and thousands of dollars with you over the years, but this was a bucker of water in the face. I'm sure I'll fly with you again, but any sort of good will I held for AA is gone."
Pros: "Half full so plenty of room to stretch."
Cons: "The plane was old. Seats seemed quite worn and didn't have the amenities (tv screens) like newer planes."
Pros: "Nothing"
Cons: "In January, we booked a 5:40pm fight through Kayak to Barcelona. July 7th, the day before our flight kayak sent us an email with a different time. Apparently, this flight had been dropped and completely changed to 5 hours later on February 2nd. Kayak didn't care to tell us until the day before. We ended up having to book a new connecting flight which cost us $250. Ive always booked with kayak and now I fear I will never again. I would like a refund for the $250 or a flight stipend. My name is sarah chambers"
Pros: "we landed. flight was on time"
Cons: "Female flight attendants were rude. I think that if they would have smiled, their faces would have cracked. Even a complete stranger said to me, while waiting for the restroom, "I think that they hate us". One young male attendant was friendly and I believe that he was training. I fear for his training experience with this group of women. One of the lavatories was out of order {....on an international flight! Are you kidding!?!}. I think that they searched for the most antiquated plane that could limp across the ocean for this flight. Nine hours of pure discomfort. My poor 71 year old mother! Zero leg room. Tiny little screen for movies on the ceiling of the middle row. trays were not clean. We paid extra for our seats and wondered how bad the seats were for those that didn't. My mother and I determined that this was ranked as one of the worst flight experiences we have ever had. We are grateful for an amazing experience for our return flight or we would have reconsidered ever flying AA again."
Pros: "Flight attendants were nice"
Cons: "The seats were incredibly uncomfortable. There was no leg room and 122 of the space below the seat in front of me was taken up by a metal box attached to the seat. I couldn't put both feet under the seat in front of me. The food was bad tasting and overly processed. We were fed a lean cuisine. The entertainment was from mounted tv's in the aisle. At this point, all planes crossing the ocean should have individual tvs for a customer to watch. They had this 15 years ago, how do they not have it now."
Pros: "The water was clean"
Cons: "Everything else! We were first sold a British airlines flight, and then we got switched to American Airlines. I don't know if that is actually an okay thing for them to do. When we got onto to plane we were stuck on the runway for over 2 1/2 hours, where the outside temperature was 95 degrees and the AC in the plane didn't work. The delay was all due to a mechanical difficulty with the engine, this did not give us peace of mind when flying over the atlantic. while up in the air my newly wedded wife and I were hoping maybe we could watch a movie to help keep our minds off the creaking of the wings, the pool of sweat from the delay, and the grumpy flight attendants. Seeing as it was a 9 hour international flight, you would have expected some sort of entertainment. Maybe a personal TV.... nope. Maybe a community TV... nope. At least they have to have a radio....... nope. All we got were our two thumbs to twiddle. After a much needed nap. We woke up hoping maybe for a hot breakfast, but to put the cherry on top of some terrible ice cream, we got a mediocre cold breakfast. All in all I will not fly American Airlines again. I would happily and quickly pay double for any other airlines but them. It's such a poor reprisentation of our country."
Cons: "Dry / borderline rude staff and hostess. Dated plane. Tiny seats. But that is pretty much the baseline of airlines in the US. When will carriers start to take note from International carriers..leaps and bounds ahead."
Pros: "We arrived on time."
Cons: "I booked with British Airways and later noticed the plane was operated for American Airlines. The seats were cramped and the online entertainment was terrible. On an overseas flight, I expect in 2017 that there will be on-screen entertainment on the back of the seat in front of me. Instead, the movie was projected on a screen in the middle seats on an overhead that was about 10 rows away. Plus, you didn't get to pick your movie. You were stuck with the selections provided by the airline. I would have brought along my DVD player or laptop had I know this was going to happen. American flight crews are not as friendly and accommodating as European flight crews, which is why I try not to select an American carrier. Seats are less comfortable on American carriers also."
Cons: "My outbound flight to Manila had an overnight layover in Japan. I asked at the luggage check-in at O'Hare International Airport if they can check it all the way through as I had planned to go outside of the Narita airport for the layover. They told me I couldn't check the luggage all the way through and that I had to pick it up from baggage claim once I land in Narita. From there I had to check-in the luggage again on the same day. When I took my luggage out from baggage claim, I tried to check-in and the counter crew told me I was given wrong information. I had to keep my luggage with me until my flight the following day. On my return flight from Manila and another overnight layover in Narita, the check-in crew at NAIA told me I could check-in my luggage all the way through, and that they also allowed this at my outbound flight to Manila. The check-in crew at O'Hare International Airport gave me wrong information."
Pros: "Free checked bag"
Cons: "2 hour delay No food to buy or drinks"
Pros: "Eventually we made it"
Cons: "Plane was delayed because a door wasn't working (old). Business class entertainment was a tablet that was collected an hour before we landed. Food was very bland."
Pros: "Streaming entertainment with great choices Not too crowded so got my upgrade"
Cons: "Food was disgusting... bland cheese lasagna or small wet noodle salad with piece of chicken. This menu has been going for years! Old B757 No sparkling water but 75 variations of Coca Cola"
Pros: "Good Entertainment. One flight attendant was great."
Cons: "American Airlines Seats were too close together. The plane was way way too hot. Asked the flight attendants and spoke to the captain after the flight as the front coach section of the aircraft was at least 10 degrees hotter than the rear. We were all taking layer of off cloths as it was so hot. Seems the first class attendants were not monitoring the temps which regulars the temps just behind first class. Told the flight attendant who also acknowledged it but the first class attendants did not make the change Many were angry. We were on the Tarmac for almost 1.5 hours waiting for the plane to be de-iced. No AC during the process."
Cons: "The quality of the plane was a real shock after the excellence of the others on this holiday. It was impossible to sleep which was really needed on this particular leg of our journey. I asked if there was a spare pillow because I had a bad back and needed lumbar support. Also we paid a lot extra to book our seats and I could really not see why. I assume it was for the pleasure of sitting together!"
Cons: "Timeliness"
Cons: "They loose my luggage!!!!!!"
Pros: "Staff put in awful position to deal with upset clients Dealt with it as best as can be expected."
Cons: "Every time we have travelled from Chicago to Toronto, the flight gets cancelled. Had to leave 0230 to get to airport only to find that flight at 0800 was cancelled. Ugh!"
Pros: "Seating is more spacious then most"
Cons: "Customa in yul is a bit of a hassle, but not that bad."
Cons: "The flight was delayed I had to wait for more than an hour"
Pros: "There wasn't anything that stood out that I could say I liked."
Cons: "I didn't care for the attitudes if the stage working in the Toronto airport. Things really aren't clear there for first-timers and much of the staff was acting like I should already know to do a lot of things when there weren't any clearly posted signs saying so. There is also a huge lack of organization."
Pros: "I got upgraded to first class!"
Pros: "Very short flight, not much to say"
Cons: "The flight was delayed twice causing us to miss our connecting flight to Copenhagen. Air Canada then put us on a flight to London and then connecting to Copenhagen we arrived at 4 PM instead of 10AM ."
Pros: "Extremely helpful and accommodating! Thanks to all!"
Cons: "Departure was late, causing me to have to run to the next gate"
Pros: "One kind guy at air Canada in Toronto who was very helpful considering the lack of help from every one else. Arrived at 2 in morning exhausted."
Cons: "Attitude of staff"
Pros: "The pilot seemed good and the staff on the plane were nice overall"
Cons: "Customer service from the group staff that checked us in was horrendous... (Lisa from Chicago ). We were not aware one of us needed eTA to fly through Canada and the agent was so belittling, rude and plane wrong with her information, that if it had not for our smarts, we might have not made it to our destination. I do not spend so much money to fly with an airline, whose agents treat it me like this! She really should be fired for her terrible manners and for giving customers wrong information..the second supervisor we talked to helped us, but the impression we got from the agent was so terrible, that it was hard to feel any good...no food on a flight during lunch hour, seems unfitting."
Pros: "I am sad to say I have little positive things to say about this experience."
Cons: "To begin, our flight was delayed an hour into Toronto. We asked the flight attendant about our connecting flight and they said they would find an answer. It ended up that we landed just as the flight was scheduled to leave. Why they could delay pur flight but would not hold another flight by 20 minutes is very questionable. Then we got to customer service, the rep told us that we could only get on the next flight going out tomorrow at the same time which meant 24 hours lost. Of our vacation- which hotels already booked and tours already booked. When I asked if there was anyway we could get in earlier the service person told me "I should be grateful because some people have had to wait multiple days to get to their destinations." When we finally did board the flight the next day we were not served any food, no snacks, and no drink for the entire overnight flight."
Cons: "There was a 90min delay on all flights going to toronto due to construction in toronto yet air canada (knowing this) boarded everyone on time anyway and made us sit on the runway for over an hour. They could have left us in the lounge until they were ready. Parents with babies do not appreciate such thoughtlessness. But hey, as far as air canada was concerned, they left the gate on time."
Pros: "In the airport Chicago to Montreal I met a nice person he made my boarding pass to me. I love the service !!!!!! Said Thank you so much for your time to getting. Dory Clothilde"
Pros: "Crew"
Cons: "Boarding gate very small"
Pros: "I liked that we got a lot of food, and the movies were very good. Groups for boarding made sense and we boarded quickly"
Cons: "it was late and despite being 4.5 hours there were no free snacks or food. Only one toilet which we could never use bc of constant turbulence."
Cons: "Airline list baggage. Had to wait 3 hours to get luggage which was put it the next flight"
Pros: "Poor airline, always delayed, dreadful and unfriendly customer service. The only reason I flew with them this short trip was due to price"
Cons: "We were in Toronto for an entire week without our bag and Air Canada showed no concern at all for our well being. I travelled with my one year old son, I needed supplies for him and Air Canada gave me dead end numbers to call, websites that didn't work and even hung up on us when we were trying to find out about our bags. They treated us terribly. I will never fly them again."
Pros: "When there were unforseen delays. They just said too bad, here is a phone number you can call. It then took 2 hours to try and get someone on the phone. Once I finally was talking with someone, they said it would cost $200 to rectify the problem. I then got put on hold. When they came back they said it would be over $2000 to get home. Talk about trying to cash is on people's hard situations. I ended up flying WestJet. They were amazing."
Cons: "My flight was changed and I wasn't informed - I cleerly checked my information beforehand but it would be nice if flights were to change by two hours, to know in advance so arrangements could be made"
Pros: "Nothing"
Cons: "Flight was late from Barcelona to Mintreal by an hour. I needed a wheelchair - didn't show up! Then pulled a muscle trying to get through customs and they barely held my flight to Chicago. Made it, with No Help. Late into Chicago and still no wheelchair. There was no one from whom to get help. Finally a United Airlines employee took pity on me and got a wheelchair to me and got me to the flight - again, just barely. Over 20 hours in the air, no assistance and poor food. I will never fly air canada again - ever. Not worth the savings. I've spent an entire week recovering and spent the savings on physical therapy due to the damage to my legs."
Cons: "horrible"
Pros: "Clean, prompt, attentive staff"
Pros: "The crew was attentive."
Cons: "The head phone slot did not work. Then the TVs went out which did not matter because I could not listen to them anyway."
Cons: "This is the third time that I flight with Air Canada and the third time that my flight got delayed. Never again!"
Pros: "Plane was super old...peeling paint, barely any full size luggage space, no in flight tv and always late or delayed. 4/4 flights we took were delayed. This airline is the worst and were terrible at keeping us updated on delays or cancellations."
Pros: "Nothing"
Cons: "Never flying Air Canada again!!!!"
Pros: "Staff was friendly"
Cons: "Uncomfortable seating"
Pros: "Nothing to like about this airline. Horrible people especially in toronto, really unhelpful, extremely rude."
Cons: "Air line decided they didn't want me to take my connecting flight. Removed my luggage without consulting with me. Offered me a disgusting hotel. Forced me to pay out of pocket for food, taxis, transfers and my own hotel choice. Staff were so rude. No explanation to why they removed my bags. I made it in plenty of time for my connecting flight but airline had just decided. No staff member was interested in answering my questions or helping. They all just wanted to sod off home. they just didn't care."
Pros: "Despite weather travel delayed I was taken care of very well. Comfortable seats. More leg room. Friendly, calm crew."
Cons: "We were not given the option to change our flight out from Chicago when we knew we wouldn't make the connection in Montreal due to weather."
Pros: "The plane was new and pretty clean"
Cons: "Food was horrible. Crew was useless. No organization."
Cons: "The departure time for the flight was 6:00am and there was no one in the check in counter until 4:15am. There was a long queue for the check in. Not a pleasant waiting time for the check in"
Pros: "Must bring your own electronic device"
Cons: "The temperature in the cabin was Frigid, even with blanket, 2 pairs of socks my coat & scarf I was freezing!"
Cons: "The person behind me kept kicking my seat and yelling at me to not recline my seat. I called a crew member over and asked if I wasn't allowed to and he said well she does have long legs. I paid for economy knowing the room that I was going to be given .. If she didn't like having her legs squished she should have upgraded her seat and the crew member shouldn't have allowed me to be uncomfortable and not having the same luxuries as the rest of the customers."
Pros: "The plane was delayed and I had a short layover so I was maybe not going to make it to my next flight so they transferred me to another airline and was upgraded to first class for free!"
Cons: "I disliked that my flight was originally at 4 pm and the one that I was changed to didn't leave until 8 pm"
Cons: "Did not appreciate not having a movie screen. Renting an iPad for such an expensive flight is not good business."
Pros: "Quick flight"
Cons: "Delays"
Pros: "The food was very good, and the alcohol was free even the second time around which i liked"
Pros: "Very friendly staff."
Cons: "Left late so missed connection. Was put up in a mediocre hotel."
Cons: "Deplaning and entering the terminal was delayed substantially."
Pros: "Very friendly crew. Smooth flight."
Cons: "No entertainment. Great person sat next to me."
Pros: "This is awful flight coz I brought it from kayak"
Cons: "Flight delayed due to plane defect. Stayed in plane for more than 5 hours. Baggage lost. Never made it on time"
Cons: "No free alcohol. Lights didn't turn off ever so I could get some sleep."
Pros: "The crew on the flight was nice, and the entertainment was good."
Cons: "Our first Air Canada flight was 2hr delayed due to mechanical error. After a 2hr delay, we finally flew for 1hr, had awful turbulence on the way down, and got to Toronto only to find out there was no customer service desk. We missed our connection with Luftanza and had to fly Air Canada again. First off, we couldn't get on another flight until the next morning. Then the desk never called the hotel they gave us the voucher for, so when we showed up at midnight the hotel was fully booked and had no room for us. We had to fly into Heathrow instead of Gatwick (final destination was Brighton for an international conference). We missed the entire first day of the meeting and had to rent a car for 65 pounds each to take us to Brighton from Heathrow, finally arriving at our hotel by midnight. The customer service was non-existent for Air Canada. We literally are going to have to email them."
Pros: "The flight was comfortable. Entertainment choices were varied and generous."
Cons: "o'Hare needs an upgrade."
Pros: "Friendly crew. Very smooth flight. Easy to navigate terminal."
Cons: "Nothing!"
Pros: "I liked the way they handled the rain delay. Although inconvenient, they were transparent with the process"
Cons: "The lack of certainty whether we were removed or stilling our connecting flight to delay."
COVID-19 information

Safety measures for airlines flying from Chicago to Caribbean

Airlines flying from Chicago to Caribbean have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago to Caribbean

Mandatory masks

Masks required on board, masks provided on flights from Chicago to Caribbean

Social distancing seating

Middle seats unavailable to book on flights from Chicago to Caribbean

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago to Caribbean

Flexible cancellations

Waiving of change fees. Search flexible flights from Chicago to Caribbean

Book cheap flights from Chicago to Caribbean

Recent round-trip flight deals

2/1Tue
1 stopSpirit Airlines
16h 07mORD-SJU
2/16Wed
1 stopSpirit Airlines
8h 59mSJU-ORD
$104
2/1Tue
1 stopSpirit Airlines
16h 07mORD-SJU
2/16Wed
1 stopSpirit Airlines
8h 59mSJU-ORD
$107
2/8Tue
1 stopSpirit Airlines
16h 07mORD-SJU
2/15Tue
1 stopSpirit Airlines
8h 33mSJU-ORD
$110
2/2Wed
1 stopMultiple Airlines
16h 07mORD-SJU
2/8Tue
1 stopMultiple Airlines
9h 12mSJU-ORD
$114
2/7Mon
1 stopSpirit Airlines
6h 44mORD-STT
2/10Thu
1 stopSpirit Airlines
8h 29mSTT-ORD
$114
2/1Tue
1 stopSpirit Airlines
16h 07mORD-SJU
2/9Wed
1 stopSpirit Airlines
7h 45mSJU-ORD
$120
2/1Tue
1 stopSpirit Airlines
16h 07mORD-SJU
2/8Tue
1 stopSpirit Airlines
10h 25mSJU-ORD
$121
2/1Tue
1 stopMultiple Airlines
16h 07mORD-SJU
2/14Mon
1 stopMultiple Airlines
22h 31mSJU-ORD
$124
1/29Sat
1 stopMultiple Airlines
29h 18mORD-SJU
2/1Tue
1 stopMultiple Airlines
8h 33mSJU-ORD
$125
2/1Tue
1 stopMultiple Airlines
16h 07mORD-SJU
2/8Tue
1 stopMultiple Airlines
9h 12mSJU-ORD
$126
2/1Tue
1 stopMultiple Airlines
16h 07mORD-SJU
2/11Fri
1 stopMultiple Airlines
8h 05mSJU-ORD
$130
2/5Sat
1 stopFrontier
29h 10mORD-SJU
2/7Mon
1 stopFrontier
8h 00mSJU-ORD
$138
4/5Tue
1 stopFrontier
14h 05mORD-SJU
4/11Mon
1 stopFrontier
21h 55mSJU-ORD
$143
2/1Tue
1 stopFrontier
18h 20mORD-SJU
2/14Mon
1 stopFrontier
22h 31mSJU-ORD
$145
3/29Tue
nonstopFrontier
4h 47mORD-SJU
4/6Wed
1 stopFrontier
12h 12mSJU-ORD
$146
2/28Mon
1 stopFrontier
8h 55mORD-SJU
3/3Thu
nonstopFrontier
5h 25mSJU-ORD
$147
2/8Tue
nonstopUnited Airlines
4h 30mORD-PUJ
2/13Sun
nonstopUnited Airlines
5h 05mPUJ-ORD
$230
1/29Sat
1 stopAmerican Airlines
6h 04mORD-PUJ
2/5Sat
nonstopAmerican Airlines
5h 12mPUJ-ORD
$233
2/7Mon
1 stopDelta
6h 10mMDW-SJU
2/16Wed
1 stopDelta
11h 35mSJU-MDW
$239
1/30Sun
1 stopJetBlue
8h 29mORD-AUA
2/9Wed
1 stopJetBlue
9h 30mAUA-ORD
$255

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Recent one-way flight deals

2/1Tue
1 stopSpirit Airlines
9h 20mORD-STT
$48
2/8Tue
1 stopSpirit Airlines
16h 07mORD-SJU
$48
4/22Fri
1 stopFrontier
23h 30mORD-SXM
$49
2/1Tue
1 stopSpirit Airlines
16h 07mORD-SJU
$49
2/8Tue
1 stopSpirit Airlines
16h 07mORD-SJU
$50
1/26Wed
1 stopSpirit Airlines
16h 07mORD-SJU
$51
1/27Thu
1 stopFrontier
8h 40mORD-NAS
$52
1/25Tue
1 stopSpirit Airlines
16h 07mORD-SJU
$55
2/6Sun
1 stopSpirit Airlines
9h 20mORD-STT
$56
1/25Tue
1 stopSpirit Airlines
16h 07mORD-SJU
$56
2/12Sat
1 stopFrontier
20h 33mORD-NAS
$66
3/30Wed
1 stopFrontier
15h 54mORD-SJU
$66
2/17Thu
nonstopFrontier
4h 37mORD-SJU
$67
3/14Mon
1 stopFrontier
27h 42mORD-NAS
$72
2/11Fri
2 stopsMultiple Airlines
26h 23mORD-SXM
$87
1/30Sun
1 stopJetBlue
8h 29mORD-AUA
$92
2/8Tue
2 stopsMultiple Airlines
15h 55mORD-SJU
$94
2/28Mon
nonstopUnited Airlines
4h 30mORD-PUJ
$107
1/29Sat
1 stopAmerican Airlines
7h 55mORD-PUJ
$110
3/29Tue
1 stopDelta
9h 10mMDW-SJU
$120

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