Find cheap flights from Chicago O'Hare Airport to Caribbean

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ORD — Caribbean
Jun 27 — Jul 41
Round-trip
1 adult
Economy
0 bags
From?
To?
Mon 6/27
Mon 7/4

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Good to know

Low season

August

High season

December

Cheapest flight

$87

Average price round-trip

$611

Good deal round-trip

$317

Good deal one-way

$148
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago O'Hare Intl to Punta Cana
(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 20% 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 Chicago O'Hare Intl to Caribbean

Scores according to KAYAK customer reviews
8.1
JetBlueOverall score based on 20196 reviews
8.2Boarding
8.2Comfort
8.6Crew
7.9Entertainment
7.8Food
Airline reviews
Cons: "Flight was delayed for 3 hrs"
Read more about JetBlue
Cons: "Flight was delayed for 3 hrs"
Cons: "My seat’s tv wasn’t working. Also, controls on the seat for radio, channels, etc. didn’t work."
Pros: "Flight left quick and everything was in order"
Cons: "Food"
Cons: "This flight was very delayed"
Pros: "The crew"
Cons: "Everything good"
Cons: "On time and very comfortable"
Pros: "Swift professional service. Pilot was exceptional; we didn’t even feel the landing or take off"
Cons: "N/a"
Cons: "Flight was late more than 7 hours with no credible explanation"
Pros: "Crew was very polite and accommodating"
Cons: "Flight was delayed 4 times. We had to cancel other reservations and wasted a day traveling instead of a quick 4 hr plane ride."
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: "El tiempo para entrar a los gates y pasar aduana fue extremadamente largo. No había organización el personal a cargo no manejo bien el orden de llegadas y turno."
Cons: "The food can be better."
Cons: "We had to wait 30 minutes for a crew member to show up which delayed our flight."
Pros: "Loved the roomy seats"
Cons: "Sound system was low quality. Hard to here the movie."
Cons: "The boarding process"
Pros: "The crew was great. We left on time & arrived a few mins early"
Cons: "I guess boarding and disembarking. Since there’s only 1 door used it’s time consuming. Some international carriers do both front and back boarding & disembarking."
Cons: "Left very late because of delayed inbound flight and need for deicing."
Cons: "The flight was delayed for like an hour"
Pros: "Decent airfare and a standard domestic flight. Nothing to complain about. Stewardess was super friendly."
Cons: "Nothing really comes to mind. Everything was fine."
Cons: "First i did check in snd told everybody that st that time 3 hours before flight they can't check the Luggage so de has to wait 20 minutes more and do the line again y just to check in the Luggage having already the boarding pass,then they change the gate 2 times and nobody knew where to go and no representive or notification there for half hour y before boarding time."
Cons: "Can’t have a free bag under the plane."
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: "It was on time, friendly flight attendant and the flight was very snooth i was so relax i fell asleep"
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: "Nothing. I didn’t get to fly and service are check in area was a disaster."
Cons: "On the itinerary my last name was missing an o and they did allow for a name correction."
Cons: "If the flight is to be delayed, the airline should notify the full delay at once , so people may have a chance to delay arriving to the airport. Additionally when the delay is over 2 hrs they should allow rebooking without penalty, because for some people the trip becalmed useless that particular day because the delay caused the to miss their reasons for flying that day"
Pros: "Comfortable seat, friendly service.The flight was also delayed due to a wing that needed to be repaired before take off. Pilot apologised and stressed that safety comes first."
Cons: "Flight was crowded. Some senior citizens were making "funny" jokes about the wing that was repaired. These jokes were not only not funny, they were making them at the top of their lungs as if they shouting to someone miles away. There were some passengers travelling with pre-teen children also speaking so loudly, it was more like shouting."
Cons: "my flight was delayed for 2 hours and there was no compensation for it"
Cons: "Almost all JetBlue employees I encountered were rude - yes I know they were frustrated with flight delays because of system failure, but at least y’all are paid. The terminal was dirty, crowded, and everything was shutting down even though people we still looking for food, beverages, Etc (so passengers make sure you are fed / prepared if you’re flying late out of Newark). There was miscommunication from almost every step and even on the play, delays were not conveyed. I’ll definitely avoid booking this flight with the airline & airport moving forward."
Pros: "Comfortable leg room"
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: "Movies didn't work and we were one hour delayed on the runway."
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: "Our experience leaving tampa to San juan was absolutely perfect! We were starting our honeymoon and as a courtsey, the attendant who checked us in, was absolutely so sweet. She even upgarded us to even more space seats at no extra charge."
Cons: "The flight back to tampa from san juan was a complete nightmare! We arrived at the gate 15 minutes before and was extremely upset to find out that the gates were closed. The pilot and the attendants saw that we were banging on the door and yet they just stared at us. The plane wasnt detached from the terminal which is why I didnt understand why they couldnt let me in unless they sold my seat. An attendant finally came out by the name of Chanel (the AD Lead). All she did is rebook me for 2 days later and told me that that flight might get cancelled due to the hurricane. She wasn't even trying at all to help me. She had a rude attitude and told me that she will be back to help me. Yeah right! She came back 3 hours later! I could not stand to even look at this unprofessional employee. I paid extra to fly jetblue as I have been told they have great customer service. Pshhhh.... I myself had to call jetblue and spoke to melinda (customer service supervisor) she was trying everything in her power and it really showed. An attendant came and started checking the next flight out of puerto rico to ft. Lauderdale. Melinda put me on stand by for the flight and ecen spoke directly to the Natalie who was checking guests on the flight. Two seats came available for me and my husband to get back to florida. We then rented a car and drove 4 hours back to tampa. I was just completely disgusted on how Chanel handled the whole situation. I told her that I had medical treatments the next morning in tanpa that I could not miss but yet she did not at all seem to care. As a lead I thought she would at least put me on stand by to go to ft. Lauderdale. That wasnt even an option for Chanel. She was completely worthless and had a stupid look on her face when she saw me get on the plane to fy. Lauderdale. Something she could have helped me with instead of saying she would be right back and left me for 3 hours later with no help. Jetblue, I say this in the kindest of ways, please fire chanel. People like that will only cost you guys more in the future as you will loose so much clientel due to the unprofessional conduct and customer service she gave. Hire more Natalie's and Melindas who help you regardless of the situation and not Chanel who didnt care and was a bother to her to put in the same type of customer service that Melinda and Natalie gave me."
Cons: "It was cold. Regulating temperature would be nice"
Pros: "Conscience and timing"
Cons: "Tv, internet did not work majority of the flight, air was not that high."
Pros: "Very good"
Pros: "Rapido"
Cons: "Avion pequeño"
Cons: "Long security lines; contradictory agent instructions; couldn't pick seat; flight delayed three times; Uncomfortable seats."
Pros: "This trip from Orlando to San Juan had a swift boarding process"
Cons: "Due to the Orlando airport that was upgrading the tram we had a additional travel time to the terminal"
Pros: "That they emailed me about the delay ahead of time"
Cons: "Most of airport was close with late delayed flight, would of like hour updates on status of flight so I wouldn't have to wait at the airport"
Pros: "The staff is great, the seats are comfortable, and the food is good"
Cons: "My daughter was unable to use her tray table due to how dirty it was."
Pros: "Very helpful customer service, really appreciate their help."
Cons: "I took two JetBlue flights within 4 days, both with delays > 2 hr for mechanical issues. I can count on one hand the number of times I've been significantly delayed in the past 5 years, especially when not in the winter. JetBlue, please fix whatever is wrong with your planes. I've otherwise had nothing but positive experiences with them."
Pros: "Smooth experience."
Cons: "Nothing."

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.

Boarding took a long time. Taking off took a long time. I spent over an hour connecting, disconnecting repeatedly from the Wifi just to watch the last 15 mins of the movie I watched on my first flight. Wasn’t offered ice with my drink. They passed me twice to throw out my garbage. And the guy next to me had his arm in my ribs the whole time.

It was a smooth flight. Nothing untoward happened

They made us check carry ons despite the entire aircraft overhead space being empty

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

Cons: "We arrived around 39 minutes early and the whole process was very smooth"
Pros: "Flight was on time and crew helped find a place for my violin. Even though I was early to the gate, they also helped me update my seat before the new flight crew arrived."
Pros: "Crew was friendly, seats really comfortable!"
Cons: "Headphones sold for $ 2. Headphones preferably free"
Pros: "The crew was not overly friendly"
Cons: "The carrots were hard and the bread was cold."
Pros: "All good."
Cons: "Price"
Pros: "The flight was on time, the crew was pleasant and looked like they enjoyed working in the air."
Cons: "Our second time on a 787 Dreamliner across the Atlantic as about the same as the the first. The seat pitch is very tight so when a passenger reclines into the next row the seatback nearly touches your face. The Dreamliner seats seem to be very hard and it's difficult to get comfortable."
Cons: "Flight was delayed a bit due to a couple passenger booking/misc issues. 1st class didn’t get gate bevfood service. Oven was busted so my meal wasn’t available. Entertainment console had all channels functional except — not really an issue I just really wanted to have ESPN playing in the background"
Pros: "Son got wings, so was happy."
Cons: "No entertainment."
Pros: "Nice service"
Cons: "It was late"
Pros: "Good snack selection. Crew was personable."
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."
Cons: "Seat assignment for me and my traveling companion was done at gate. We had to sit in 2 different rows."
Pros: "Crew was nice and welcoming"
Cons: "Well, if our plane had been leaving on time it would've been superb."
Cons: "Notify the delay quickly"
Pros: "Helpful"
Cons: "More print media to read on"
Pros: "Crew was great."
Cons: "Couldn’t hear/understand the pilot"
Pros: "Flight attendant in first class was amazing."
Cons: "It was delayed"
Pros: "N/A"
Cons: "Chinese Eastern did not try to help and solve my problem."
Pros: "There was a bit of a mixup in boarding the plane but otherwise the flight was good. There was no entertainment system on this short flight. The flight attendants were very pleasant & efficient. They only served snacks on this short flight but were very good at ensuring everyone had at least one or more beverages. The premium seats were very comfortable ."
Pros: "Short flight"
Cons: "Flight attendant was not willing to go above and beyond as he stated he would. My husband asked for a coke and the flight attendant told him he could only get water."
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: "Snacks, cleanliness and crew"
Cons: "N/A"
Pros: "Nothing"
Cons: "They take them forever to find me another fly ,make miss my other fly, my work my time and my sleep"
Cons: "Entertainment app from Go Go didn’t Work."
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."
Pros: "I was with my friend"
Cons: "Delayed 12+ hours"
Pros: "We had a 2 1/2 delay due to mechanical issues but the crews, flight and ground, did a great job. Thanks."
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: "Staff were friendly and boarding was and getting off was easy because flight was super empty. Timeliness was appreciated too."
Cons: "Seats don't recline far enough."
Cons: "It takes time and worries to find the air train and Aeroflot registration."
Pros: "My flight was great. Boarding was easy and the seats were comfortable."
Pros: "Giid free sandwixh. Very good entertainment system. Good seats."
Pros: "I needed to run real fast to the connection flight and gladly got there on time."
Pros: "The service was amazing , the staff was honestly friendly and nice"
Pros: "Great service, nice agent friendly"
Cons: "I was unable to fly at all due to a spelling error on my ticket. The airline refused to alter the ticket. Worst experience of my life, ruined my Christmas"
Pros: "Entertainment is very good"
Cons: "Send my carry on bag, outside."
Pros: "Very nice flight and attentive staff. Enjoyed the view of NYC as we flew up the East River, then looped over Nassau County to approach LGA."
Cons: "The male flight attendant who handed out the complimentary drinks and snacks acted a bit strangely. I was very thirsty, and I asked him if I could keep the rest of the can of soda. He neither said yes nor no, but rather completely ignored what I said and just poured my drink and moved on. I was a mildly annoyed, but figured maybe it was policy and he was shy and didn't want to debate the matter. When he took care of the older couple behind us, however, things got really strange. He asked them whether they wanted pretzels or peanuts, but they misheard him and asked for a ginger ale. I happened to know that he did have ginger ale, since my wife had just gotten one, but rather than just pouring the old folks a drink, he repeated himself. "Peanuts or pretzels?" They misheard again and asked him whether he had a diet ginger ale. Again, rather than just pour them the drink, he repeated himself. "Peanuts or pretzels?" This went round and round a few more times -- like a poorly designed computer UI that refuses to accept anything except the correct input -- before the old couple finally figured out the disconnect and picked their snacks before their drinks. Very weird."
Cons: "Layover"
Pros: "N/A"
Cons: "2.5 hour delay for no apparent reason at first (supposed mechanical issues with plane) and then waited on plane at gate for a missing pilot who never got picked up from his airport and got stuck in Chicago traffic trying to get to O'Hare. Eventually had to take pilot from another flight before leaving at 8:45 when flight was scheduled for 6:00am."
Cons: "Small plane"
Cons: "The seats are very uncomfortable but other than that it was wonderful!"
Pros: "Service and comfort"
Cons: "Food"
Pros: "On time"
Cons: "Meals and more options to drink during flight. No entertainment system"
Cons: "Had an issue with my passport and the manager at the check in counter was rude and not helpful."
Pros: "Great crew; efficient, kind and accessible."
Cons: "Entertainment system. Tiny screens and no options."
Pros: "The food"
Cons: "Everything ok"
Cons: "Copa check-in in Chicago was awful, and it wasn’t just for my family and me. The manger and several employees were rude and seemed clueless about what they were doing. I shouldn’t be surprised that none of our luggage arrived because of the unorganized check-in but it just added to the frustration."
Pros: "Good food (especially the Fruit platter we get when departing from Panama and the Guayaba juice that's available in all flights), very short layover, short flying time, allowed 2 checked bags plus a carry-on and a personal item."
Cons: "Web-checking still a little buggy (I'm not allowed to web checking when going to the USA, when departing from the USA and my destination address is in a different country I'm still forced to choose a US State to continue). Also Panama Tucumen Airport is awful, crowded, expensive and usually dirty."
Pros: "On the flight from Chicago to Panamá crew was exceptional, friendly and attentive, I was very impressed with the service,PLEASE DON’T CHANGE ANYTHING , from Panamá to Costa Rica the crew was completely different, the service was efficient but not friendly, a smiling face makes a difference."
Cons: "The process of boarding was a little confusing but it went quickly, keep up the good work"
Cons: "Food on COPA is terrible."
Pros: "There is nothing to like because this flight never happened."
Cons: "Instead of going Chicago -> Panama City I was routed to Chicago --> Newark --> Bogota --> Cartagena. This means instead of arriving 8pm, I would now be arriving 8am the following day (I actually arrived after 1pm, so all in, it was about 30 hours of travel experience). At the request of the United agent in Minneapolis, I got in Customer Service line in Chicago to have my bags properly transferred to my connecting flights. After an hour in line, the agent proved to me by showing me the screen she was working on, that my bags would be routed directly to my final destination. She was confused why I was told to even come in line, so, great, another hour wasted."
Pros: "excellent service"
Pros: "Everything"
Pros: "The seats were comfortable, they served a free snack and also a adult beverage"
Pros: "Very friendly service and very helpful even though there is a language difference, they were great in making me feel comfortable."
Pros: "Nothing"
Cons: "Very old, uncomfortable airplane. Business class is a joke. Cabin temperature Was either too cold or too hot"
Pros: "Everything was great!"
Cons: "-lost my luggage -no entertainment on flight from Panama to Punta Cana"
Pros: "Good servoe"
Cons: "No WIFI connection movie selections"
Cons: "Uncomfortable seats. I ordered Kosher meals, but they did not have any available, so I pretty much watched everyone else eat while I couldn't."
Pros: "copa is punctual with the flights and offer a good service in the air."
Pros: "Service was excellent"
Pros: "The crew was great the food and service"
Cons: "For a 5 hour plus flight would have liked a more updated cabin with a charging station for electronic devices and possibly an entertainment center"
Pros: "Drinks"
Cons: "No entertainment OR WIFI?!"
Pros: "The staff was extremely helpful and pleasant. It seems like everyone spoke English and Spanish. Free drinks. A fine flight."
Cons: "Not a thing."
Pros: "All. A lot better. Of. Any. USA are line"
Cons: "All"
Pros: "The crew was really nice"
Cons: "There weren’t good options on food, and even it’s a 5 hours flight there was not internet or screen on the chairs."
Pros: "They provide any of your requests is they have it"
Cons: "Everything was fine"
Pros: "Crew was courteous, and very polite."
Pros: "Short flight and thankfully I slept a bit."
Cons: "The stewardesses just say in their area. Never offered extra coffee or drinks. No snacks. Food was pathetic."
Cons: "Older plane with less room from Chicago to Panama, but other than that everything was great."
Pros: "Seats didn't recline, entertainment was poor."
Pros: "My trip went really smooth with no delays. They were able to switch my seat to be closer to my friends that were flying with me with no hassle at all. I was surprise that they provided food on the trip, I have been in different airlines that don’t provide anything except for a drink. I would for sure use Copa Airlines for future South American trips"
Cons: "Only thing I might of dislike is that they were using an older plane and the tv quality was not good"
Pros: "The crew and staff were wonderful and professional"
Pros: "Nothing. Even when it's the cheapest flight, th insignificant price difference vs. other airlines doesn't compensate the awful experience"
Cons: "The treatment of the crew was unrespectul. The food is extremely bad. The airplane and seats were uncomfortable."
Pros: "Duration of flight."
Cons: "Food"
Cons: "Flight was overbooked and I got bumped. Needs to be ther for work very inconvienant"
Pros: "The food and flight crew were good. Both of my flights they served breakfast, just for reference."
Cons: "Checkin was poorly operated and the return flight had no inflight entertainment. I have never been on an international flight with no entertainment. There are certain expectations for flights that cost that much."
Cons: "Hice el webcheck in y aun asi me pusieron de ultimo en toda línea, entiendo que habian los que se quedaron del dia anterior, pero puso estrés en mi, también salimos tarde, y mas valijas se quedaron en Chicago y en lugar de mandarlas a mi casa, tuve que viajar 3 hours al aeropuerto y recogerlas yo misma despues que me habían dicho que las mandarían."
Pros: "Service of crew excellent. On time and good arrival. Web check in let me pick my seat. And nice stewardesses"
Pros: "Service."
Cons: "nothing"
Pros: "Flight was on time and affordable."
Cons: "No drinks were served in first 2 hours, and meal was very small. Also no customs forms were handed out in the flight, so it too a while in the airport to fill it out."
Pros: "Loved that I was able to take 2 suitcases with me... Happy about meals on flights and headphones! Captain kept us informed at all times about everything!"
Cons: "my table was dirty and I noticed right before my meal was served."
Pros: "Liked the dairy free options for the meal."
Cons: "Didn't have an individual tv to watch movies on, or cell phone charger. Given the price however, this was acceptable."
Pros: "nothing"
Cons: "custumer service"
Pros: "Planes are clean and crew is nice"
Cons: "Overall they are a poorly organized airline and there is almost no entertainment."
Pros: "plane was comfortable"
Cons: "Flight attendants weren't very polite."
Pros: "Comfortable leg room Friendly cabin crew"
Cons: "Very limited food options, International flights have poor entertainment options, Very old seats and covers gave a very dull impression"
Pros: "The check in staff are the first port of call. They were excellent and very friendly and helpful. It set the scene for the rest of my flight"
Cons: "One of my bags did not arrive in Panama. They tell me it is now on my ongoing flight to Belize .....we'll see!"
Pros: "They had a vegetarian pasta option and the crew is always friendly!!!!"
Cons: "We were an hour late arriving. Boarding was slow."
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."
Cons: "Delay"
Pros: "The place to charge the phone is easily accessible on the back of the seat in front (as opposed to underneath)."
Cons: "Did not like that I had to check my bag at the gate"
Pros: "Crew was very good."
Cons: "Seat 2L Rocked back-and-forth every time person in seat 1L moved. This was a day flight from Chicago to London so I wasn’t sleeping. I could see if you were sleeping and had to deal with all the seat movement it would not be ideal."
Pros: "Left on time and arrived early"
Cons: "Delayed"
Cons: "Couldn't turn on reading lights the entire 8 hour flight to Hawaii! 8 hour flight and only a wrap to eat. Not even food offered for purchase in the last 7 hours of the flight"
Cons: "Great ! Next time please confirm seats before boarding"
Cons: "The flight was delayed by over 3 hrs! As a result I missed work!"
Pros: "The tv and drinks"
Cons: "Being told why we’re delayed and then not being kept on board for so long once we arrived late"
Cons: "I was bumped off the flight due to weight restriction and moved to a flight 6 hours later, it only took me 4 hours to rent a car and drive home. I am a 210 lb 6ft tall male. I was not the reason for the plane being over weight, I was there before boarding took place they didn't ask and I didn't fly."
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"
Pros: "American Airlines Crew, friendly and personable"
Cons: "N/A"
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!"
Pros: "Easy boarding crew were friendly food was hot"
Cons: "Seating was a pain to try and get 2 seats together even though I booked it months in advance very noisy rude people couldn't sleep on a supposed overnight am exhausted"
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."
Cons: "Three hours delay. I paid for a upgrade to first class. But because of the flight change i didn't get to keep my upgrade and I had to beg for a refund. I have had two trips in the past 5 days and all flights have been anywhere from 1 to 3 hours late. Worst experience with AA I have had in a long time."
Pros: "Nothing - the flight from Chicago to Philadelphia was delayed by about 2 hours. Luckily, was able to get the flight switched to a Chicago - London direct flight."
Cons: "The connecting flight from Philadelphia to Manchester would've been missed. So, American Airlines booked the same flight for 24 hours later. Luckily, they offered a different flight. Due to the flight changes, the prepaid ground transportation from Manchester to Leeds wasn't used. Transportation from London to Leeds had to be purchased at a much greater additional expense."
Cons: "I got tranafered to 4 different gates aand my flight was delayed for 3 hrs with no explaination and the staff didn't try to help"
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: "How much tighter can they cram us? I'm 5'11" and 185 pounds and was too wide for the seats!"
Pros: "Clean plane. Excellent service. On time."
Pros: "Amazing entertainment selection, comfortable."
Pros: "Loved having 2 empty seats next to me so I could stretch out after a very long day of travel."
Cons: "Seats are not very comfortable in any position."
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: "The crew, the movies, and window seat"
Cons: "Didn't like how tight the flight was. Way too compact and 3 seats near window seats makes it so uncomfortable."
Pros: "Flight was on time."
Pros: "Staff courtesy."
Cons: "When I started this leg of my trip, I was completely exhausted having been in sitting position for almost 24 hours straight. Airline made no concessions for travelers knowing that some were just doing a simple trip and those others whose journey was very long. Narrow seats added to stress and discomfort. Airline policy seemed to be "Give me the money and I will deliver you safely. Period" Humanity seems to be last on airline list. Traveling is seriously grueling and unpleasant for all those not in First Class."
Pros: "The American Airlines crews and people manning the desk erred very professional. Yes, this particular flight was conducted by American for Iberia under a share code. So whatever horror stories you have heard of about European Iberia flights, the one I took was fine. But the airline's crew is being let down."
Cons: "In Chicago, our flight was delayed at least three hours for a "GPS update." The crews said the software wasn't even handshaking. Okay. But I have a feeling this is common, and wish the airline would figure out a way to conduct updates, safely, without impacting everyone's schedule. My wife flew through same connection on the same airline a week later. And her flight was canceled. Maybe for the same issue? Unsure. It could have been a a bad luck streak."
Cons: "They were late because of bad scheduling and the gate agent was rude"
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: "Nothing"
Cons: "They did not compromise when I couldn't go, I understand no refund but I cancelled a few days after,"
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: "United airlines canceled a flight last minute that I needed in order to get to my best friends' wedding on time, I usually fly AA but the United flights were slightly cheaper at the time. The options United gave me would have had me missing the wedding, AA had more flights that allowed me to make it in time, considering it was booked 12 hours before take-off, it was decently reasonable and left on time and got in early (imagine that, United). Thank you American Airlines, again!"
Pros: "The crew was very efficient and friendly while handling everyone. Flight was smooth, food was good. I went to the wrong terminal and did not know that the advertised finair flight was actually American Airlines, the AA ticket counter attendant went all out to make sure I made it to the gate. All this with less than an hour before departure."
Cons: "I went to the wrong terminal, the email ticket had finair in large print and in smaller print indicated American. Luckily I was able to literally run and make my flight. Would be better to more clearly indicate actual airline."
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."
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: "I sat next to a friend I haven't seen in almost a year"
Pros: "The entertainment selection was wonderful."
Cons: "The flight left on time but arrived late by at least 1/2 hour. I am small but the seat was narrow: my neighbors kept on hitting me when they moved. And I think it is terrible to have to pay to reserve almost any seats except for the middle seats."
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: "Crew was excellent but it was literally the most uncomfortable plane ride I have ever been. There was even an empty seat in the middle and I couldn't sleep at all. The seats were super shOrr and the headrests sucked"
Pros: "Entertainment system has a good selection"
Cons: "No earphones to listen to the soundtrack on the entertainment system"
Cons: "Where to begin? The pilot suggested we would "probably miss our connecting flight" but not to worry because he would be "moving quickly" through the air. Missed my connecting flight. Ended up stuck in Charlotte with no more flights to Florida. And the airline left my bag in Charlotte. Disaster."
Pros: "Very affordable! Traveling can be difficult, especially from Chicago O'hare - one of the busiest airports in the country - but everything was made easy for me and was a breeze!"
Cons: "No complaints here!"
Pros: "I had my first experience in the Admiral's Lounge at O'Hare and enjoyed it very much."
Cons: "My traveling companion's tray table was disgusting when she folded it down for beverage service. She asked for a wet towel and the flight attendant was snarky but went to get one without even looking or asking to see what the problem was. Her entertainment console wasn't working so they reset it but instead it reset mine (two seats over) they did this again and I let them know it was resetting mine. I was told that I was not in the seat they were resetting for ...I inquired if perhaps they should try to reset mine and see if it would, in fact, fix hers..it did. When she slipped off her shoes the carpet was soaking wet. This was a really crummy, crummy flight."
Cons: "Timeliness"
Cons: "Good flight"
Cons: "The flight was delayed I had to wait for more than an hour"
Pros: "I got upgraded to first class!"
Pros: "We had a very good experience with Air canada and will use Air Canada again."
Pros: "Nothing"
Cons: "Flight delay led us to miss our connecting flight. Air Canada then lost our luggage for 6 days on our honeymoon!"
Pros: "Very short flight, not much to say"
Cons: "They airline cancelled our return flight and booked us on another flight more than 2 hours later. We had an event to attend that night so we asked if they could book us on United so we wouldn't miss it. The agent outright lied and said there were no other United flights before then. As we were waiting for our flight, we heard the agents call the final call for a flight to Chicago. Truly disgusted with Air Canada - will never fly them again!"
Cons: "The seats are large, but they tilt forward. I'm 6'2" and have anxiety issues related to spinal problems. That forward pitch in the seat (half way up the seat) is an painful problem for people like me."
Cons: "Departure was late, causing me to have to run to the next gate"
Pros: "Not much."
Cons: "I thought Comcast service was bad. This was the worst. They cancelled my flight at the last minute, then escorted all passengers out of the gate, told us to go through customs then pick up our luggage. And said we had to call to arrange another flight, but the phones just left a message saying to call back in a few days. I was stranded with no phone, no hotel, and no flight home. Three days later, I still cannot get in touch with them."
Cons: "See above."
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."
Cons: "My original flight was delayed by 3 hours, causing me to miss my connecting flight. Instead of arriving at 9:30 at my final destination I arrived at 1:30 am. Exhausted."
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: "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: "short trip"
Cons: "delayed but didn't update the screen as delayed even though it was delayed an hour it still said on time."
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."
Pros: "When I had to reschedule they were very nice about making sure that I had the information I needed and they gave me great seats on the way to London."
Cons: "My flight was Delayed and I had to reschedule that was unfortunate."
Cons: "Delayed"
Pros: "Great Pilots The pilots were great! The weather was not optimal, but they did a great job of making us as comfortable as possible."
Cons: "Better Quality Food Needed The salted plate served was sub-standard. Also, it was full of salt and poses health risk for many people. In the past, better food was served including a pot pie. Also, the staff should be more aware of the wines to be served. And there is not enough attention paid to service in the executive cabin as the attendant runs back and forth between both cabins."
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: "Staff was friendly"
Cons: "Uncomfortable seating"
Pros: "The crew was very friendly."
Cons: "The plane boarded early and the food was not good. The pasta was over cooked and essentially a mash."
Pros: "Everyone I came in contact with was amazing and super helpful!"
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: "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: "Quick flight"
Cons: "Delays"
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: "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 was great, food was alright, and overall I enjoyed my flight"
Cons: "the only entertainment was able to connect to apple products or a renatble iPad. I don't have an apple product so that was a bit annoying"
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: "How quick it waz"
Cons: "How close the seats were"
Pros: "Friendly crew. Very smooth flight. Easy to navigate terminal."
Cons: "Nothing!"
Pros: "The crew was good!"
Cons: "I wished that there were opportunities given for beverages. I also would have liked more explanations on how to connect to the entertainment."
Pros: "I like having the trip map in front of me so I can track progress. Usually I don't get it on flights this short."
COVID-19 information

Safety measures for airlines flying from Chicago O'Hare Airport to Caribbean

Airlines flying from Chicago O'Hare Airport 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 O'Hare Airport to Caribbean

Mandatory masks

Masks required on board, masks provided on flights from Chicago O'Hare Airport to Caribbean

Social distancing seating

Middle seats unavailable to book on flights from Chicago O'Hare Airport to Caribbean

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago O'Hare Airport to Caribbean

Flexible cancellations

Waiving of change fees. Search flexible flights from Chicago O'Hare Airport to Caribbean

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