Find cheap flights from Chicago to Caribbean Islands

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Wed 3/1
Wed 3/8

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Latest Caribbean Islands Flight Deals

Best round-trip prices found by our users on KAYAK in the last 72 hours

MOST POPULARPunta Cana
1 stop from $224
1 stop from $100
Montego Bay
Nonstop from $193
1 stop from $90
Santo Domingo
1 stop from $202
1 stop from $96
Nassau
1 stop from $228
1 stop from $73
Oranjestad
2+ stops from $286
1 stop from $129

Good to know

Low season

February

High season

December

Average price round-trip

$655

Good deal round-trip

$271

Good deal one-way

$125
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 12% increase in price.
(avg. price over the last 2 weeks)
or less
or less

Top tips for finding cheap flights to Caribbean Islands

  • High season is considered to be January, February and December. The cheapest month to fly from Chicago is January.

FAQs - booking Caribbean Islands flights

Top 5 airlines serving from Chicago to Caribbean Islands

Scores according to KAYAK customer reviews
8.1
JetBlueOverall score based on 19432 reviews
8.3Boarding
8.2Comfort
8.6Crew
7.9Entertainment
7.8Food
Airline reviews
Cons: "Was 2hrs behind schedule"
Read more about JetBlue
Cons: "Was 2hrs behind schedule"
Cons: "This flight was very delayed"
Pros: "Free wireless"
Cons: "I'm not in Charlotte"
Pros: "Seats are comfortable, main reason I like this airline. Crew was nice."
Cons: "The screens on the back of the seats are showing their age and the controls on the armrests are causing your neighbor to change your channel or the brightness of the screen. Letting everyone stream content to their own devices would probably be a better option, with safe charging available."
Pros: "Service was awesome, 100% recommended"
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."
Cons: "The food can be better."
Pros: "Unbelievable for the price."
Cons: "Nothing bad to say."
Pros: "Great flight and experience!"
Cons: "Left very late because of delayed inbound flight and need for deicing."
Pros: "Pilot did great job at landing."
Cons: "Flight was delayed without explanation and airplane was quite old."
Cons: "2 hours late!"
Pros: "Clean plane"
Cons: "Took 3+ hours to get in the plane"
Pros: "It was a great trip for the cost."
Cons: "Nothing."
Pros: "Free WiFi. Cute vids for Holloween"
Cons: "Nothing!"
Pros: "Nothing"
Cons: "Being delayed from 6am to 1:30pm"
Pros: "I appreciate that they let families with strollers board after Group A, there seems to be more space than the major carriers, and the snacks are good!"
Cons: "My Satellite XM radio didn’t seem to be working."
Pros: "Seat space for each passenger"
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: "More leg room Affordable prices Snacks dunkin donut coffee Pleasant flight attendant Punctuality"
Cons: "Nothing"
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: "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: "The seats were comfortable."
Cons: "Flight was very late leaving Chicago. We sat on the plane for quite a while (over 30 min) shut up tight with little air circulation AND no information about why we were not leaving the gate. Flight crew were not very friendly - almost "marched" up and down the aisle and barked at people."
Pros: "Adequate leg room and ability to take a carry on we if your extra charge"
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: "comfortable seats TV great beverages--actually get can or bottle"
Cons: "when we checked it, did not put us together"
Pros: "Seats were pretty comfortable with decent legroom."
Cons: "Plane was freezing cold, but a blanket had to be purchased."
Cons: "The flight was delayed and we would have missed our connection in NYC. So we had to cancel the trip."
Cons: "TV screen was working for some, but not for others."
Cons: "my flight was delayed for 2 hours and there was no compensation for it"
Pros: "Our flight attendant Jeramy was FABULOUS!!"
Pros: "The comfort of the seats are amazing. I was able to sleep through almost all of the flight."
Pros: "No gate, waited 2 hours in plane"
Pros: "Everything is ok"
Cons: "Not a thing"
Pros: "The plane had more room overall than comparable and more expensive flights from other major carriers. The crew was professional and efficient."
Cons: "Food options were limited and unappealing, though pretty standard for industry. Flight was short in duration ~3 hrs, so not a real issue.. I thought that selling blankets and pillows was very cheap BUT that savings is reflected in ticket cost and a better flying environmemt and experience from start to finish."
Cons: "Turbulence was terrible, understand that is not JetBlue issue - wanted to note."
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."
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: "Boarding system efficient. Lots of leg room. Choice of snacks. Good service."
Pros: "Entertainment on board"
Cons: "My flights was delayed"
Pros: "Gave me my refund!"
Cons: "Flight was delayed 5 times without sufficient reason. Weather was clear. Had to ask for a refund after the 6th delay. Missed an important event."
Pros: "This was my first time with JetBlue and I was pleasantly surprised with the size of the plane. It was pretty comfortable"
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"
Cons: "Both ways my flight was significantly delayed. Although Jet Blue sent me notices, none of those came before I was on my way to the airport."
Pros: "Kosher snacks! Thank you. Screens and outlets at every seat. Safe, controlled Covid protocols including de-boarding. Excellent!"
Pros: "Delta flight took extra precaution to keep all passengers safe before during and after the flight. They communicate effectively during the flight. I will be flying Delta again and again."
Cons: "The trip was great"
Cons: "We arrived around 39 minutes early and the whole process was very smooth"
Pros: "Super friendly and helpful with connections."
Cons: "The music on the plane was a bit much. Lol"
Pros: "Crew was friendly, seats really comfortable!"
Cons: "Headphones sold for $ 2. Headphones preferably free"
Pros: "Calm and safe, just like I like it."
Cons: "The carrots were hard and the bread was cold."
Pros: "Comfortable plane due to few passengers"
Cons: "7 hour delay after flight postponed."
Pros: "Got to my destination without any issues"
Cons: "Seats/seating area are too small, and I'm not a big person."
Pros: "All good."
Cons: "Price"
Cons: "No AC for an hour before takeoff - very uncomfortable. Audio for tv did not work."
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."
Cons: "It was late"
Pros: "Good snack selection. Crew was personable."
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."
Pros: "Jeff was our flight attendant in first class. He is an excellent flight attendant. He has an amazing attitude and his manner made us feel as if we had been friends with him for years."
Cons: "Passengers who pay retail for first class on domestic flights should get access to the Delta lounges even without the AE card. Other airlines do this, and we have come to expect it."
Pros: "The boarding was fast and very well handled."
Cons: "My flight from Chicago was two hours late and that's why I missed the flight from Atlanta to Buenos Aires. No one helped and did not know that the flight was delayed and I had to find a place to sleep. I'm not satisfied with the experience and I have not yet arrived in Argentina because of the whole"
Cons: "It was delayed"
Pros: "N/A"
Cons: "Chinese Eastern did not try to help and solve my problem."
Pros: "It was a smooth boarding, flight and exit out of the plane."
Pros: "Snacks, cleanliness and crew"
Cons: "N/A"
Cons: "From the begging they changed the flights for something totally different. It was a 14 hour trip. Awful"
Cons: "Entertainment app from Go Go didn’t Work."
Pros: "It was a normal flight as well expected."
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."
Pros: "I was given a complimentary upgrade."
Pros: "It was great"
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: "The service was amazing , the staff was honestly friendly and nice"
Pros: "Great service, nice agent friendly"
Pros: "Very friendly and professional gate agent and flight attendant"
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: "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."
Pros: "Nothing"
Cons: "Cancelled my flight because I lost one of the arms"
Cons: "Layover"
Pros: "Short flight"
Cons: "Too cold Not friendly boarding agent"
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: "Had a death in the family and no one would help me get back home"
Pros: "Seats were comfortable. Snacks!!! Nice flight crew."
Cons: "I liked everything."
Pros: "The Gogo Inflight wifi and entertainment did not work for even a minute. I choose flights based on their amenities and this one had offered full WIFI service which swayed me to choose to fly with Delta. I'm not sure who is to blame about this issue but I'm pretty frustrated that it was completely dysfunctional."
Pros: "The movie I watched was pleasant, although I had trouble hearing it because of the situation described below."
Cons: "There was a family seated behind us with several crying, loud children. We were miserable. Even my headphones with a Mozart sonata cranked up to loud did little to mask the noise. Probably not Dela'a fault, but the crew did nothing to mitigate the problem."
Cons: "Plane was sat broken at gate and needed part to be flown in. 150 minutes delayed. Not acceptable."
Cons: "The seats are very uncomfortable but other than that it was wonderful!"
Pros: "Service and comfort"
Cons: "Food"
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: "Good"
Cons: "Good service"
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."
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: "Roomy seats."
Cons: "One bathroom had a faulty toilet. The other had a door that would not lock. Some seat back pockets were in bad shape."
Pros: "puntual with great service"
Pros: "Service was good"
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: "Evrything fine!!!"
Cons: "No whell chair wait for me only this!!"
Pros: "Great crew from Chicago to Panama City. Accommodating and attentive."
Cons: "Ah, the usual airline stuff that we just have to live with."
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: "Food was ok"
Cons: "No WiFi, no outlets, no entertainment for international flights seems very outdated."
Pros: "Wouldn’t let me on the flight."
Cons: "After checking in via the mobile app, the front desk said they didn’t have me registered therefore didn’t know I was coming despite being at the gate well before the flight departed. Additionally, Kayak made it extremely difficult to consult with the issue. Very dissatisfied with the whole experience."
Pros: "Friendly service, food and drink included, and free luggage. Seats had limited leg room, but otherwise comfortable. Would select this airline again!"
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: "The food and service"
Cons: "Maybe more entertainment for a 5 hour flight"
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"
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: "Great service."
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."
Cons: "Late departure"
Pros: "Planes are clean and crew is nice"
Cons: "Overall they are a poorly organized airline and there is almost no entertainment."
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: "Food and drinks."
Cons: "Bad entertainment selection and screen."
Cons: "Not enough smiling from the crew"
Pros: "attendants were very friendly and the flight was on time."
Cons: "Business class seats were really economy seats in a closed section (this is the norm on flights operated by Copa Columbia)."
Pros: "Nothing"
Cons: "Individual TVs, perhaps"
Cons: "Late and then mechanical issues."
Pros: "Crew was great"
Cons: "Seat was uncomfortable. Flight was much too crowded"
Pros: "Flight was cancelled after multiple delays & I changed to United."
Cons: "Stop delaying & canceling flights, especially last minute"
Pros: "Really easy boarding and flight. Great in flight entertainment options."
Pros: "All was good"
Cons: "Nothing to complain about."
Pros: "Seat assignment process was great and considerate of my preferences."
Cons: "If AA could fix its luggage handling process that would be great. BOTH (!) of my bags have been lost on this flight. Both have been eventually located, recovered and delivered to me, but experience was not pleasant this time."
Pros: "Flight attendants were friendly and thoughtful."
Cons: "Seating is too tight. Hard to believe that in 2019, major airlines still have seats without any electrical or UBS outlets for charging devices."
Pros: "Crew was great."
Cons: "Plane was about 1000 years old and I don’t think I’ve sat in a more uncomfortable seat."
Cons: "Unable to connect to the new AA so-fi"
Pros: "Comfortable seats and snack / drinks service"
Cons: "Delayed flight departure and bumpy landing"
Cons: "I was apparently "flagged" by British Airways for extra security checks. As I understood it in London, I was randomly selected for this security check. This then apparently meant that I was to be flagged for all subsequent flights. This meant that in Chicago, after going through two other security checks that day (Zurich and London) and completing customs, I had to engage in a full Homeland security check. This involved removing protective covers from my laptop and phone that were hard to get off (not meant to be taken off regularly) and a full body search that I did not have to do in London. After many hours of traveling, this was very a frustrating experience."
Cons: "I will never, ever book with Kayak again"
Pros: "Flight crew was great. The plane was half full, so the attendants allowed us to move."
Cons: "Terrible landing in Charlotte. The plane was rattling and had an annoying whistle."
Cons: "British Airways/American Airlines lost/delayed luggage again! Then send an email in the middle of night with a link to schedule home delivery of the luggage that was valid for 4 hours only. It is clearly an attempt to cheat out of their responsibility of home delivery of the luggage that was delayed the second time. Poor, poor service by American Airlines."
Cons: "It was not clear that I needed a different 6 letter code to checkin using the AA website. I finally got frustrated and called AA only to find out the code was different. The codes should have been the same or you should have referenced it on the website when I tried to check in"
Cons: "Flight was delayed for more than 4 hours with little communication from staff as to why, gate was changed to a gate across the airport."
Pros: "The boarding was quick and easy as well as the crew was friendly and accommodating. Great end to a fun weekend away."
Pros: "Our plane was late getting to the gate. They kept us informed and turned it around pretty quickly. There were storms between Chicago and Rochester so we were rerouted. As a result the hour flight was an hour and a half. The pilot kept us informed and it was a very smooth flight. So even though I was over an hour late arriving I so appreciated the communications and the safer route. AA seems to be communicating more than other airlines and I appreciate that. Flying is absolutely no fun anymore so you take what you can get for the positives."
Cons: "WiFi wasn’t working so I couldn’t communicate my late arrival to family picking me up."
Cons: "On my first flight from SLC to ORD I asked 3 different American Airlines employees if I needed to pay for my carryon before I got on the plane. They all said no. I got on the plane, put my carryon under the seat in front of me and everything was great. I landed in Chicago, got to my gate, went to board and this very rude employee stopped me after I scanned my ticket and told me I couldn’t board with my bag. The EXACT bag I had boarded with in SLC. After harshly grabbing my bag and putting it in the carryon basket to check for size, she wouldn’t let me pass by her into the boarding bridge and told me I was going to have to pay. I tried explaining that I had asked I’m SLC if I needed to check it and they had all said no and that it fit under my seat. She said, “I don’t care what they said in SL, this is what I’m saying here.” And directed me to the front desk where I had to pay $50!! $50 for a carryon backpack that fit under my seat comfortably 20 minutes before!! Without saying a word (cause I didn’t want to yell at the poor girl behind the desk) I paid the $50 and proceeded to enter the bridge but before I passed through, the rude woman said, “have a nice flight ma’am” and scoffed!! An audible scoff. So I’m short, I hate American Airlines and I will do my BEST to not have to fly with them in the future."
Pros: "The fact that they re-booked without me having to contact customer service."
Cons: "The connecting flight was cancelled while boarding was in progress at the start of the journey."
Cons: "Flight was delayed by untold circumstances causing us to miss our connecting flight to Venice."
Pros: "On time departure and early arrival"
Cons: "Nothing"
Pros: "Nice crew Spacious plane"
Pros: "The crew was amazing, flight was very smooth, arrived early, plane clean, service was great."
Cons: "For being in first class, my seat did not recline so I couldn't sleep and audio for my entertainment center was not working"
Pros: "Good time for flight"
Cons: "Tight, hot inside plane, no refreshments"
Cons: "They left the lights on the whole flight"
Pros: "They alerted me to problems with our flight and we switched to an earlier flight. No problems with new flight. Good service."
Cons: "Great trip"
Pros: "Not turbulence"
Pros: "Was on time."
Cons: "Not eventful."
Pros: "crew was great, plane seemed newer and clean. individual screens worked better than others I've used in flights."
Cons: "newer touch screens were great except viewing angle couldn't be adjusted. standard food was horrible, esp for an international flight; not sure if specialty diets have better meals. kid movies were dubbed into many language options but Chinese was not one for ANY kid films. bathrooms with the same crappy mini sinks that you can't really wash your hands in, esp if someone pukes in it. they should all learn from Japan's ANA airliners with the motion sensor sinks with faucets raised up high enough for you to wash your hands without touching the gross basin."
Pros: "On time, good service."
Cons: "Luggage did not make the transfer on time (Chicago-Charlotte after Tokyo), although they had about 45 minutes to load it. Do not buy an international ticket with less than 1.5 hours transfer time. (It took 45 minutes to get through customs/immigration and retrieve luggage for transfer."
Cons: "Missed it."
Pros: "Nothing"
Cons: "An S80? Really? This plane was older than me! Horrible plane! The crew looked like they had been up since 4 am. Looked exhausted and unfriendly. I do want to clarify that this was an American Airlines operated plane, not etihad."
Cons: "The cramped space"
Cons: "All was excellent! Only the internet was not working good , payed for all flight access but most of the time the internet was not working. Anyway I contacted support team and they refunded me"
Cons: "The flight was delayed more times than I can count, we got a different reason each time. Weather I can understand, but telling us we are waiting on a specific crew to arrive and then announcing that crew is not for our flight was just terrible communication. No one seemed apologetic. The only thing they did was bring a snack cart over for us, and that got raided by children so many people didn't get anything. We had arranged transport from Orlando to Tampa for that evening, and our rides had to cancel because instead of 7pm we were now arriving at 130am. Your airline's mistakes put everyone at an inconvenience and we weren't offered assistance to fix it. My husband went to ask for help in arranging new transport home, but he couldn't even get to the front of the line. The customer service was terrible. We really enjoyed our first leg of the flight home with American Airlines, but after the second leg and all of the problems we had... we will not fly with American Airlines in the future."
Pros: "on time"
Cons: "very cold"
Cons: "This made the check in process extremely frustrating and confusing. Traveling with my elderly dad who had to squeeze between two large men for 7 hours because people who actually booked the airline got priority seating. We had to pay an extra $500 to upgrade to comfortable seats. Not pleased w Kayak."
Pros: "The crew was great and getting 2 meals was very nice."
Cons: "My headphone jack kept malfunctioning (loud popping noises in my earbuds) while watching the movie and all the reading lights came on and stayed on the majority of the flight so sleeping was difficult."
Pros: "An agent found me a window seat for the Chicago-Barcelona leg of the trip with extra leg room. That was amazing. Also, the lost luggage assistant for American Airlines was super helpful and nice. Also, the 787 (I think that was the Chicago-Barcelona craft) was a very enjoyable airplane. It was super smooth. It had high tech windows that adjusted the amount or type of light that could filter through the windows depending on the settings."
Cons: "When I arrived in Barcelona my Bag went missing. It showed up an two hours after my flight landed."
Pros: "I enjoyed the entertainment because I don't watch movies in the theater often. The movies I saw in-flight were recent films I've been wanting to see and made time pass fairly quickly."
Cons: "I'm not a giant, but there definitely was not enough leg room in the main cabin. I could not sit comfortably, especially in the middle seat."
Pros: "Good flight. Arrived on time"
Cons: "Jet bridge was broken and needed repair. Delayed departure."
Pros: "The crew were exceptionally friendly and helpful. They made the negatives about the flight much more bearably be their excellence service whether during boarding, in flight, or after landing."
Cons: "I booked the flight originally through british airways and expected your standard, modern plane for cross atlantic travel. Boarding to find myself on a 767 designed (and likely built) in the 80s was rather disappointing."
Pros: "Seats were really neither notably comfortable nor notably uncomfortable. I think they were slightly on the comfortable side."
Cons: "Would be nice to have more modern aircraft amenities, like power outlets for device charging, and display screens with at least some complimentary entertainment, or at least flight path tracking. Boarding counter lady was obnoxiously strict about not letting our carry-on bags to be carry-on. She made us test them in the size device and said they were too big, even though they could easy be pushed into the space, and regardless of the fact that we just flew on an American Airlines flight with them as carry-on and were only on a layover with them! Regarding the previous AA agent who let them be carry-on, she said "shame on them." Complete opposite of the positive experience we had with her counterpart in Phoenix. ಠ_ಠ"
Cons: "They cancelled the flight and put me to fly the next day"
Pros: "Everybody was nice my ride was comfortable and they treat me with respect"
Cons: "I like everything"
Cons: "Terrible. Flights delayed by 90 minutes. Then on boarding we as a couple weren’t sat next to each other on the four across plane, but in the two aisle seats. This was bad. But then no one was sat next to my wife. So an empty seat, my wife, me, then a stranger. C’mon Air Canada, figures it out."
Cons: "Good flight"
Cons: "They loose my luggage!!!!!!"
Cons: "The train at Chicago airport was broken. I walked to get the next gate to the other terminal."
Pros: "Upgraded to business class."
Pros: "I got upgraded to first class!"
Cons: "This flight was operated by United Airlines, a code-shared flight."
Pros: "We had a very good experience with Air canada and will use Air Canada again."
Pros: "It was overall a good experience, cannot complain about the service as it was great."
Cons: "The weather caused a bumpy return flight but that is not the airlines fault."
Pros: "Very short flight, not much to say"
Pros: "Extremely helpful and accommodating! Thanks to all!"
Pros: "Everything I will definately be back"
Cons: "See above."
Pros: "Long wait for ticketing and at customs during transfer"
Pros: "The crew were helpful and professional."
Cons: "The options for movies and music for the inflight entertainment were not that good. The AirCanada app for mobile devices was not as user-friendly as I expected it to be."
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."
Pros: "Air Canada is my favorite airline to fly. The employees are always helpful, from checking in to the flight crew."
Cons: "I only wish Economy had more leg room."
Pros: "Crew"
Cons: "Boarding gate very small"
Cons: "They lost our luggage and we didn't get it all back until about 7 days after we arrived! 7 Days!!!! Customer service was horrible and we were traveling with a small child."
Pros: "Flight was smooth; love being able to track route. Got in early."
Cons: "Flight was delayed but overall trip was good"
Pros: "Smooth take off and landing."
Cons: "The numbers above the seating arrangement cause a lot of confusion for people and some almost want to argue for the window seat."
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"
Cons: "It was so great we didn't go. Got a refund you retards"
Pros: "We were able to switch to an earlier flight. gate agent was very helpful"
Cons: "horrible"
Pros: "Clean, prompt, attentive staff"
Pros: "In flight entertainment. Friendly staff."
Cons: "Slight delay but related to the weather and not to the airline."
Pros: "There was nothing redeeming about this flight."
Cons: "Delay caused us to almost miss our flight to Dublin. Rude staff, and overall disappointing. I will not be flying on Air Canada again."
Cons: "Delayed"
Pros: "Nothing"
Cons: "Never flying Air Canada again!!!!"
Pros: "Staff was friendly"
Cons: "Uncomfortable seating"
Pros: "Everyone I came in contact with was amazing and super helpful!"
Pros: "Staff were friendly and helpful"
Cons: "Delays leaving the gate led to longer delays taking off."
Pros: "The flight seats were great. Spacious, charging ports, cheap flight, and had entertainment in-flight."
Cons: "The engine was making an unusually loud whirring sound. Felt concerned that the plane was not fit to fly."
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: "Very friendly staff."
Cons: "Left late so missed connection. Was put up in a mediocre hotel."
Cons: "Not enough time to go through customs. Missed connection."
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: "Provided a blanket and pillow, breakfast and dinner, had 3 bathrooms which was excellent for how many people on the plane. The flight attendants were excellent and very nice as well. I do love air canada for long flights."
Cons: "When i checked out the cabin after i bought the tickets i was under the impression that there would be screens on the plane to view movies for free. Instead they were offering for $10 to buy a ipad and more money for headphones to rent for the flight to watch movies. Kind of was a disappointment but i read a book which is always better to do anyway."
Pros: "The crew was very nice."
Cons: "It was like flying in 1995. They may want to consider buying more modern planes."
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"
Pros: "good entertainment but otherwise average or less"
Cons: "No free alcohol. Lights didn't turn off ever so I could get some sleep."
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: "On board service Comfortable seating and space On time dep. & arrival"
Cons: "None"

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