Find cheap flights from Caribbean Islands to Chicago

Find cheap flights from Caribbean Islands to Chicago

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Boston (BOS)
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Good to know

Low season

JanuaryBest time to beat the crowds with an average 4% drop in price.

High season

JanuaryMost popular time to fly with an average 11% increase in price.

Average price round-trip

$378(avg. price over the last 2 weeks)

Good deal round-trip

$153or less

Good deal one-way

$151or less

FAQs for booking flights from Caribbean Islands to Chicago

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Top 5 airlines serving from Caribbean Islands to Chicago

Scores according to KAYAK customer reviews

8.1
JetBlue
Overall score based on 19,466 reviews
8.3
Boarding
8.2
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews

Pros: "The pilot provided us with a trip that felt more entertaining and expedient."

Pros: "Comfortable !"

Pros: "Yes"
Cons: "Good"

Cons: "."

Cons: "Todo fue Exelente..."

Cons: "Yes. Delay by 4 hours. I got the notification when I was at the airport."

Pros: "Staff was amazing, and the movie selections are always good"

Pros: "Amazing landing"
Cons: "All good"

Pros: "The luggage waiting time was 0!"

Cons: "Good"

Pros: "Everything was amazing...."

Cons: "JetBlue is amazing and my favorite airlines for domestic travel."

Cons: "Nada"

Cons: "You get what you pay for"

Pros: "The space was very comfortable."

Pros: "It was on time"
Cons: "My Screen didn’t work"

Cons: "clearly communicate delays. We had no idea what was happening or what our options were."

Cons: "Need more vegan food options"

Cons: "El vuelo se atrasó demasiado"

Pros: "El personal es muy amable"
Cons: "Que no viajen mas para la ciudad de Santiago de los caballeros en D.R.es una pena de verdad para mi ."

Cons: "We waited at least 8 hours in the delay and I wasn’t texted early enough to plan ahead. We waited in the airport and then we waited on the turnpike before take-off."

Cons: "legspace"

Pros: "LOTS OF LEGROOM"
Cons: "They have a habit of not being ontime"

Cons: "The new security check in with the automated bins."

Pros: "Natalie was not pleasant I asked a question and she ignored my questions"
Cons: "I aske Natalie if there were any sit available so that my husband and I can sit together she quickly responded with out looking in the computer"

Cons: "Asked the stewardess to have a blanket and water she had not brought. Service was bad ."

Pros: "Nothing"
Cons: "Late and unstable"

Cons: "2 hr delay. Poor ventilation"

Cons: "Nothing"

Cons: "The 3 hours delay"

Cons: "Delay and 4 hours in the craft upon arrival to Chicago"

Cons: "Very cheap food , only cockies and water"

Cons: "Another plane mechanical issue causing another delay of over 2 hours."

Cons: "The have problems with the movies"

Pros: "Puntualidad"
Cons: "Todo bien"

Cons: "Cancellations after cancellations due to the aftermath of hurricane Maria through Puerto Rico. A lot of missinformation taken from the airlines."

Cons: "Delay the fligh two times"

Cons: "It was great!!!"

Pros: "On time. Very organized. Great price."
Cons: "Nothing"

Cons: "Never got on it."

Cons: "It was too cold inside."

Pros: "What can I say? The trip to Punta Cana was smooth."

Pros: "Everything on time."
Cons: "The seat in hard."

Pros: "Everything!"

Pros: "Fatal"
Cons: "Muy malo el viaje"

Pros: "Everything"

Pros: "I wasn't able to make a seat selection on line. When I went to the counter I was given an extra room seat which I appreciated. Unfortunately this seat was next to someone with a dog. I don't like dogs due to unpleasant childhood experiences. I was able to change my seat with no problem. Thank you."

Pros: "Fast boarding, excellent costumer service."

Pros: "Everything went to plan. Very nice."
Cons: "Nothing"

Pros: "Everything was great. Seats, service, flight, crew."
Cons: "N/A"

Cons: "Not a thing!"

Pros: "Cabin crew was great. Was told they don’t feel they can do a good job of serving 48 passengers in Premium Select with 2 crew."
Cons: "Image recognition step slowed boarding down a lot. Food and amenities on Delta Premium Select seem to be getting worse"

Pros: "Fast service and precise timing"

Pros: "Great comfortable seats"
Cons: "Crowds in airport"

Pros: "Comfort is excellent"
Cons: "When traveling with the pet, personally always travel to Puerto Rico, we take our cat, I would like Delta to have the option of making the reservation online until paying for it, although you should always call to confirm, that would be super excellent."

Pros: "Nothing exceptional stands out"
Cons: "Flight was not on time"

Pros: "Clean plane. On time"

Cons: "They have to improve the boarding process a bit."

Pros: "Smooth ride"
Cons: "Seating"

Pros: "Flights were both timely"
Cons: "WiFi on flight from Atl to Tallahassee wasn’t working at first"

Pros: "Amazing service from crew"

Pros: "The entertainment"
Cons: "Space between"

Pros: "I missed my flight and you guys helped me catch the next one :D I was able to still make it yo my final destination within the same day"

Pros: "On flight entertainment was very good. Flight was smooth and ran ahead of schedule."
Cons: "They were out of vegetarian meal options. Really poor for a six hour flight. Also, the family behind us was atrocious, but that’s not Delta’s fault."

Cons: "Was refused to use the 1st clas restrooms but 10 minutes layer the flight attendant allowed an older gentleman and a lady to use them. I was in 10A with my service dog"

Cons: "Bigger personal space"

Cons: "No room to move very cramped"

Pros: "see above"

Pros: "Excelent flight excelent service.."
Cons: "The entrance in the gate to the plane always disorganized"

Pros: "My flight from STX was delayed some 30 minutes. That made a dent in the 57 minutes I had to catch my Delta flight. Naturally we landed at gate A2 and Delta was boarding at Terminal 2 gate B9. Me with my knee replacement can’t run and my wheelchair was not in sight. Thank goodness I had a carryon with wheels. I was out of breath when I got to Delta and the last passengers were boarding. I started panicking and interrupted the ground steward who asked me to wait with a smile. I waited . So when I told them I was standby they waved me on after showing my passport. I couldn’t find my boarding pass. I was pleasantly surprised to get a seat in first class. I was so thankful. My first time. Good things come to those who wait! Thank you Delta."

Cons: "Entertainment system wasn’t working"

Pros: "I like the fact that entertainment and technology is always good."
Cons: "Boarding is always a horrible experience. I never know what zone is boarding. Your agents at the gates are overwhelmed with so many things."

Pros: "Service was great, crew was responsive, snacks were good per usual."
Cons: "The AC was blasting at an all time high, felt frozen to my seat, even asked for a blanket but “ they didn’t have any more “, had to tuck in my arms into my layered shirt. this was a morning flight and no breakfast was served ... they didn’t even have food available for purchase."

Cons: "N!A"

Pros: "Nothing"
Cons: "Flight delay 5+ hours poor Service"

Cons: "The bulkhead sears had no electrical outlet"

Cons: "Flight delayed 2 hrs"

Pros: "After almost every airline cancelled. Delta still took me to where I needed to go with not one single problem. That pilot was amazing. I forget his name. But the plane didn't slide or anything during take off. Amazing."
Cons: "What was there not to like. We were a little bit late but I wasn't in a rush. I planned well ahead. Delta moved my flight from 10 a.m. to 6 a.m. and that was perfectly fine with me."

Pros: "Once we boarded the plane, we still had to wait for the pilots to arrive and then for them to run through their pre-flight checking before we could get underway."
Cons: "The flight was delayed and the departure gate moved at the Atlanta airport 3 times to 3 different concourses before we were finally able to depart around 1 hour later than scheduled."

Pros: "Was initially hoping to fly a US airline but will now look for Aeromexico first. Exceeded my expectations!"
Cons: "The layover in Mexico City was a bit long and the airport was not so great"

Cons: "Cancel my flight at 7:50 am to 1:50pm"

Pros: "Boarding, checking in etc. The usual stuff, nothign spectacular."
Cons: "Seats are getting too crowded!"

Pros: "The crew was beyond friendly and courteous. Lots of leg room."
Cons: "I was an older plane, it was louder than our flight down to Atlanta. Nothing they could do about it, but a slight annoyance."

Pros: "Everything. I really loved that I could track where my checked luggage was, so when I arrived to my final destination I knew my bag was going to be there. The individual TV for my seat, so I could watch what I wanted. Having an USB port to charge my devices."
Cons: "Liked everything."

Pros: "No hubo retraso y salió todo el vuelo a tiempo. El personal fue atento."
Cons: "El espacio entre asientos es mínimo y es súper incómodo. La experiencia fue de incomodidad."

Pros: "Friendly and informative flight attendants kept the passengers in reasonable spirit."
Cons: "Left nearly an hour late after confusion related to oversold seats and upgrades. The gate agent entered the plane multiple times. The landing was rough, the brakes were loud."

Pros: "In flight entertainment interface and options were great!"
Cons: "Very uncomfortable!! Spent the entire flight with my knees pressed against the seat pocket. One flight attendant was somewhat rude and unpleasant."

Cons: "I don't know why delta's service has deteriorated so much in the last few years. Last two times that I flew the service and attitude at the gate has been horrible. Seat assignment has become a dread. Upgrade options are over priced. I guess I will be looking for a new airline."

Pros: "Everything"

Pros: "The crew was friendly and accommodating, and service was good"
Cons: "I purchased a basic economy ticket and upon checking in, my Delta app said my seat was unassigned and I had to get my boarding pass at the airport. I checked back later and the app had me as number 7 on the standby list. I called Delta (wait time 3+ hours... my flight was in 3), and then the Delta app support where I was able to get through to someone. She told me that the ticket I purchased over a month in advance did not guarantee me a seat on the plane (???). She said that if I was bumped from the flight they would reschedule me for the next morning. She was pretty rude and made it seem like I had a 50/50 shot of getting on this plane. I rushed to the airport in hopes that I would be the first from Standby there, and the gate agent told me that I was fine and would board right after first class and be assigned a seat then. Great. Once I got my seat assignment, I board to find out there is someone else sitting in my seat...... They eventually called the desk and had her moved, but it was the weirdest boarding experience I've had.. and I've flown Spirit. These planes that Delta fly's are SO OLD. Both times I have flown Delta the "turbulence" has been so bad and cold air was blowing right on my the whole flight with no option to turn it off (it wasn't from one of the vents, but from the side). Someone close to me works for Delta and I know for a fact that some of their engines blow mid-flight.. and they tell the passengers that it's turbulence.. so that doesn't make me feel very safe. I won't fly Delta again if there is another comparable option."

Cons: "Headphones suck"

Cons: "Flight attendants were a little snobby and didn't treat all passengers equally, in my humble opinion (note: I was sitting in 1st class)."

Pros: "The plane was surprisingly comfortable. The seats had USB ports. The touch screens were clear and responsive. Most importantly, the service of the flight attendants was excellent. I was quite happy."

Pros: "Always have great experience with Delta flight attendants and staff. The entertainment on mobile phone was a really nice add-on, I had never seen before."
Cons: "Flight was delayed in taking off, waiting for connecting passengers. Plane was old, which is most Delta planes, but this one showed it. The tray table looked like it was from the 70s or 80s. Flying into Midway instead of O'hare was anticlimactic."

Pros: "The onboard entertainment system was awesome.seats were comfortable."
Cons: "Flight was a bit bumpy."

Pros: "The gate agent was very helpful."
Cons: "The seat was very tight because the person who was next to me leaked over the arm rest into my space. I had a window seat. Also I had a torn ACL and requested a seat with more leg room and it was not assugned."

Pros: "Great Delta crew at check in and boarding!"
Cons: "Rear of plane very hot after passing through a very cool front. Service without a smile. "Don't have that" monitors on seats were almost useless."

Cons: "Seats too narrow"

Pros: "The pilot did a good job flying considering the conditions."
Cons: "Delta and Midway airport did not handle the weather conditions as well as they could have. Communications we terrible and no one adapted quickly to handle things properly. Of course the winter weather alert was mostly to blame, but what could be done to smooth things out didn't happen."

Cons: "Get with the times and stop using plastic cups."

Pros: "Great"

Cons: "I cant think of anything at the moment."

Cons: "They canceled the flight last minute and I had to spend the night and I missed work and a doctors appointment. I asked to be put on another flight and they told me to wait and when I asked again they said they couldn’t cuz the flight left. If they would have changed it in the first place then I woud"

Pros: "see previous comments"

Pros: "The crew was wonderful. They were very attentive throughout the course of the flight."

Cons: "Follow through with reservations made 6+ months ago. I shouldn't have been on stand by and the vouchers to make up were absolutely ridiculous. $10 does not make up for the major mistake your company made."

Cons: "Good service"

Cons: "Nithing"

Cons: "Too warm in cabin. Someone was sitting in my seat 7D and actually began to negotiate w me to sit somewhere else."

Pros: "It got me back to Chicago."
Cons: "It was so uncomfortable - the seats were horrible and the temperature on the plane was way too hot the entire flight."

Cons: "Queria pagar la diferencia de 5 boletos a Business Class y la del mostrador me dijo que no se podia. Tenia que ser 5 horas antes???? Gordita Dominicana aragana !!!! No quiso vender e hizo perder a su empresa. El Business tenia suficientes espacios. Mal personal el de Copa. No recomiendo la linea aerea."

Pros: "Food was great, crew was great."
Cons: "This flight did not have the screens for each seat, leaving no choice to choose what to watch or to see flight info."

Pros: "TV options, meals, check in"
Cons: "The bus shuttle in Panama and in Bogota."

Pros: "the meal was nice."
Cons: "that I was crammed into a seat. I was seated in the back row and the person in front of me leaned their seat all the way back and because of my height I was literally stuck. Flight attendants wold roll eyes if I didnt understand their spanish immediately or spoke english to them."

Pros: "The breakfast was good, warm, fruits were fresh."

Pros: "Leg room, crew"
Cons: "Old equipment"

Pros: "The stewardess was very unprofessional and being racist"

Pros: "Always is on time"

Pros: "Smooth flight, made up for lost time"
Cons: "Very unpleasant experience with crew generally. Very surprising, given previous experiences with Copa."

Pros: "The seat had extra leg room, BUT..."
Cons: "The seat's cushion was pulled out from the backrest, making it a very uncomfortable seat & giving me Backpain. (This was the seat next to the window, not the middle seat.)"

Pros: "The flight attendants were good to everyone and the plane was either new or very close to it"

Pros: "Great overall experience. Hassle free."

Cons: "Lo últimos grupos deberían pasar primero."

Pros: "Perfect"
Cons: "No complaints"

Pros: "I got upgraded to first class. Awesome experience"

Pros: "The food was pretty good."
Cons: "After boarding the plane, we sat on the runway for like 30 minutes waiting to take off. Nothing was said and no explanation was given as to why we had to wait 30 minutes to take off."

Cons: "We did not have the little TVs"

Pros: "Same"
Cons: "Same"

Cons: "I went through security at Lima Peru (Jorge Chavez International), everything was fine. I arrived to Panama, and the gate was next door which is just great awesome. The bad part was that I had to go through a security check once again there, although I had not left the airport since I left Lima. I went through the exercise, I was told that there would be no liquids (8 oz bottle of water, soda, etc) allowed passed that check point. Yet they were selling these items next to the gate. It made no sense why this checkpoint and why the liquid restrictions. Once in the area if I wanted to go use the restroom or whatever I needed to go through the checkpoint. There were 6 Copa employees manning this station, that's extra expense that the company passes on to the flyer for a step that should be evaluated and look at to see why other airlines do not do this. I was not the only one getting frustrated with this setup, but also passengers that did not speak Spanish they could not communicate with Copa employees. I saw this liquid restriction with Spirit Airlines in Lima, and I decided not to fly with them any more, no matter how inexpensive their fares were. Spirit told us that it was US law that made them have people throw away their drinks, although they were bought in a secured area. To me this was just a way to charge for drinks on the plane. I never had to throw away my drink if I had bought it in a secured area."

Pros: "On time departure from the gate."
Cons: "To board the plane in Panama City passengers had to go through a second security screening and were therefore unable to bring bottled beverages onto the plane. Once through this second security there was no where to purchase water. The free never came through the plane to offer more beverages after the meal service. Many passengers got up and corralled at the back of the plane to get water. I watched a flight attendant drink from one the large bottles herself and then presumably serve to a customer."

Pros: "Food was decent. All Crew very helpful and polite."
Cons: "I wished the longer flight had personalized entertainment in each seat instead of the shorter flight. I could have watched two movies on the longer flight instead of just one."

Cons: "Why would you put a cartoon on to watch??"

Pros: "Loved the check in. No baggage expense. Up to two bags FREE! Then, we had a meal --that was included in the fare. The crew was pleasant and accommodating. Everyone was pleasant. To pass the time on the 5 1/2 hour flight, there were options for movies, TV, games and etc. Overall, it was a pleasant flight. When I book my next trip, I'm going to see if Copa goes there. If so, that's my first choice."

Pros: "LOVED the individual TV's on each seat"

Pros: "The food"
Cons: "Maybe a lil more movies"

Pros: "Friendly and Courteous employees. Flights were on time."
Cons: "Gates were not available upon arriving at destinations. Once we had to take a shuttle bus from plane to gate."

Pros: "They gave me a upgrade!! What else did I want."

Pros: "Made it home safe"
Cons: "Seat didn't recline and horrible gas smell. Blower didn't work."

Pros: "I love the comfort in these planes and also the fact that at least they serve food, which they don't do in other airlines. The boarding wasn't good due to the stupid restrictions the US imposes on flights to the USA. We didn't appreciate the fact that the airline didn't let us know in advance that we couldn't buy drinks at the airport. That was a waste of money. The food wasn't good at all though. The coffee was terrible and so were the eggs, but at least we got something."

Pros: "Copa allows two bags of 50 pounds to be checked along with carry-ons. They provide a full meal on each flight (at least that we've been on). The crew is accommodating, even providing more than one drink. The chairs are fairly comfortable."
Cons: "The headset didn't work well."

Cons: "Nelson Jose zelaya durmió en una sill en ese aeropuerto porque no lo dejaron hacer conexión a punta cana que era su destino; porque nunca dijeron nada tanto el Consulado de Panamá como la aerolínea que cuando una persona ha sido deportará de US A no puede viajar; utilizaron el fly que estaba comprado para su devolución al país de origen; ustedes creen es justo?"

Pros: "Nothing. Everything was a bad costumer service."
Cons: "I missed my flight because in the town I live , there was a landslide and rocks fall on the road. And it was impossible to get out of the town and I didn't find any help for refunding or changing the dates of my flight. Really bad costumer service, I'm still waiting for a reply of the emails I sent to vayama. Imposible to comunicar with it by phone with them and with the kayak office in Colombia."

Pros: "I liked the fact that there was variety for entertainment! There had great movies, new ones, not all airlines focus on that. Another thing was the food and drinks that the offered. They really kept passengers happy."
Cons: "N/A"

Pros: "Everything"
Cons: "Nothing wrong. Complete perfection"

Pros: "All of my grievances regard the Panama staff at the airport and on the plane, the staff and services at O'Hare were top notch. Customs was extremely fast and efficient and everyone was friendly and did their jobs well. As far as the Panama airlines go, the food was okay, nothing special but not disgusting, and not all the flight attendants were unpleasant."
Cons: "The worst thing that happened was mean spirited security guards at the airport did a security check before allowing us to get to our gate. They forced us to dispose of a bottle of water that we had bought at that very airport. We were then quarantined into a waiting area with no seating and no access to other water, bathroom or food. Then on the plan we were offered beverages twice, so I was only able to get about six swallows of water from Panama to Chicago. Dehydration makes a plane ride a lot less healthy and comfortable. The staff was mostly unpleasant, the seats were really small and uncomfortable (more so than any other airplanes I've been aboard), and for some reasons they kept turning the main lights on and off, allowing us to sleep and then waking us all up for no good reason. Unbelievable."

Pros: "The people from Copa are so helpful answer questions I like that."

Pros: "The service by the crew in providing the food and drinks was excellent."

Pros: "Great and friendly"

Pros: "Don't you know this information already?"

Pros: "Everything was great. But the American Airlines can improve on not letting non-first class passengers use the restroom up front."
Cons: "The food! Bring back real food please"

Pros: "Flight on time!!"
Cons: "Cramped space, no leg room. Seat 17A won’t recline"

Pros: "Safe flight"
Cons: "On time departure and arrival."

Pros: "Our seats were booked by a cruise line and were not together on this flight. When my husband asked, the gate agent was able to seat us in at least the same row."

Pros: "On time"
Cons: "Flight attendant had some attitude as if they were not enjoying their work."

Pros: "Ok time flight"
Cons: "Entertainment system did not work in all stops"

Cons: "The flight attendant was arrogant. This is her job... just for $$$"

Cons: "I traveled with this carry on for numerous flights and for the last three legs of this trip w/of having to check it. For some reason they made me check it. because I had to spend time at the baggage claim carousels I almost missed the last train of the night back home. Fortunately all is fine, but it caused unnecessary stress."

Pros: "It is good"

Cons: "No tv on seat. Those dumb comedy tv show"

Pros: "I had a great experience overall. I don't give 5 stars because there is always room for improvement no matter how good your service is."
Cons: "Size of the snacks"

Pros: "How spacious it felt and there were film selections"
Cons: "My film kept stopping randomly."

Cons: "The boarding experience is awful. I wish that there was more order to the boarding process such as with Southwest Airlines. There is simply no control over rude passengers who push there way to the front."

Pros: "at least flights were on time. 20 minutes delay is not bad."

Pros: "Nothing."
Cons: "Cramped, claustrophobic space. Cabin too warm."

Pros: "It was very inexpensive and on time. And it was much more comfortable than those budget airlines like Spirit, Frontier, etc."
Cons: "The snack choice was unappealing."

Cons: "The touch-screen entertainment system was not very responsive. It was difficult to get the screen to recognize your selection."

Pros: "Aircraft comfort and entertainment options"

Pros: "I like it! Thank you, kayak"

Pros: "Friendly and prompt service."

Pros: "personal entertainment systems and charging plugs"
Cons: "only pretzels and no headphones offered for the entertainment systems."

Cons: "Aircraft need to be updated. Or price should be credited when you get such an old aircraft."

Pros: "Entertainment and great beverage options"

Pros: "Seat were comfortable and I didn't feel claustrophobic."

Pros: "Todo muy bueno"

Pros: "The staff was friendly and helpful"
Cons: "There was a ton of turbulence"

Cons: "Boarding late"

Pros: "Friendly staff Smooth ride On time"

Cons: "20 min delay at Dallas International"

Cons: "Always delayed"

Pros: "NOTHING"
Cons: "Everything. DELAYS___DELAYS"

Pros: "Pretty comfortable"

Pros: "It was great."
Cons: "Everything was good."

Pros: "On time."

Cons: "Got cancelled"

Cons: "I am still not feeling well to travel, so I was staying at home and no Madrid, may be in the fall or winter when I get better, I will visit Madrid one more time."

Pros: "very smooth, ontime ride.. kool"
Cons: "everything was ok"

Pros: "Delays caused a little stress but all in all a good experience."
Cons: "Late arrival to DCA."

Pros: "The TIMING AND ATMOSPHERE"

Pros: "It was fine. I was comfortable and I slept throat most of it."

Pros: "Not much"
Cons: "We sat on the tarmac for an hour after we landed. Missed my connection, no other flights that night. It wasn't even 10 pm yet."

Pros: "Everything was very professional."

Cons: "90 min late"

Pros: "A breakfast offering at any time would be great."
Cons: "Too many people getting on at same time."

Pros: "Boarding was smooth"
Cons: "It was fine"

Pros: "Good"

Pros: "Roomy & comfortable seating for such a small aircraft"
Cons: "Late boarding, over an hour"

Cons: "Gate changed and baoarding time changed countless times."

Cons: "No tv."

Pros: "Both planes were delayed"
Cons: "I did not appreciated getting to my destination so late."

Cons: "Gate changes 6 different time Delays a lot Bad airline horror not recommended"

Pros: "the crew was great!"
Cons: "The plane was very dirty"

Cons: "My flight did not go to Chicago. United changed our flight without notifying us. Instead we went to DC. Almost missed our plane."

Pros: "United provided excellent service for my return from Puerto Rico to the mainland. Unlike other carriers, United quickly adapted to the reality on the ground and adjusted their schedules accordingly. The result was a safe, comfortable, flight for a very reasonable cost given the very short amount of time I had to make reservations. Thank you!"
Cons: "Seriously? Landing on one end of one terminal and having my connection at the end of another?"

Pros: "The crew Personnel was courtesy and there were friendly."
Cons: "I didn't like the process of me having either laptop or some kind of computer to see the TV set because I can't afford that and that's why I had to be looking side-to-side to watch TV also changing to Gates when I got to Chicago I had to change three gates C24 B6 and B2 it was too much changes in a short time that has to be improved."

Pros: "Helpful crew"
Cons: "Almost lost my job because of the flight cancellation and delays."

Cons: "The flight attendant was super rude an racist to one of the passengers"

Pros: "Had a complimentary drink given to three of us because some rain water leaked in as passengers were boarding the plane. The staff was excellent beyond that!!!"
Cons: "Our flight was late leaving and for some reason when I checked in on my phone it said I needed to see an agent for my seat assignment"

Pros: "Excelente"

Pros: "It was an over night flight and I usually fall asleep on those, but sometimes I have to wake up due to noises etc. This wasn't the case. Thanks"

Pros: "Chairs, charging stations onboard, courteous flight attendants, onboard entertainment."

Pros: "I like the boarding process and the confort."
Cons: "My birthday was yesterday, August 22, and we were traveling to Atlanta, and at the San Juan airport the flight to Chicago was delayed so we upgrade to first class because we don have enough time to get birthday diner in the stop in Chicago to Atlanta, so the thing was that they didn't have enough meals for the costumers, they were 2 meals short , my husband couldn't eat so we ask for other options and they only had 2 thing that my husband couldn't eat, because they were horrible. So that brought my husband mad, so it was not enjoyable because every time he tried to do something to feel calm again but they couldn't do anything to help us calm down. They keep telling us that it was her mistake that she miscounted and that they didn't give them enough snacks, we didn't had snacks for the rest of the flight it was stressed full. Tomorrow i have to travel again back to Puerto Rico, and im scared that tomorrow will be a horrible day traveling with United, with no space for being comfortable with no food for 9 hours, im worried that the flight is delayed again and that a lost my flight back home, were my dogs are in a hotel till that night so im scared to have to pay another night for my dogs, and I wouldn't be able to pay it. I hope you could help me to figure something out to make this experience more enjoyable my phone number is 7876440442 Zaimee Esteves and Gian K Cruz"

Cons: "That you have to pay for a movie and snacks."

Pros: "All good"

Pros: "Nothing"
Cons: "Turbulence"

Pros: "Great service. Free Internet and movi9"
Cons: "Seat next to the restroom"

Pros: "Cleanliness of plane"

Pros: "Great staff. Great safety explanation. Smooth fight"
Cons: "Nothing. Everything was great. I'll definitely try to stick with united for my future travels"

Pros: "arrived on time despite delayed departure"

Pros: "Flights was ontime"
Cons: "Plane was too hot, and then way to cold. This seems to be a re-occurring problem. I am not sure why the plane can't just be set to be be 68-72 degrees. There is no need for it to be above 80 or less than 60."

Pros: "Lots of turbulence"

Cons: "Delayed three times"

Pros: "Nice plane for a small one"
Cons: "Bumpy ride."

Cons: "The seats didn't bend back to be comfortable. Only 1 inch!!! The back was restless"

Cons: "Departure from Chicago was delayed"

Cons: "The very very long delay"

Pros: ". We got back 30minutes early then schedule!"

Pros: "Pilot got is there 25 min early"

Pros: "Attendants were very personable and friendly. I loved that they brought multiple rounds of water throughout the flight. Communication was great and no waiting times. Wonderful flight home after a wonderful vacation!"

Pros: "Cost Ease of booking"
Cons: "delays (weather based )"

Pros: "On time."

Pros: "Everything else was fine"
Cons: "Not a lot of smiles"

Pros: "Still deciding"
Cons: "All flights were late."

Pros: "Quick check in!"

Cons: "Delayes"

Pros: "Trip was on time and a good experience overall."
Cons: "No Coffee"

Cons: "Lack of comfortable space. :-("

Pros: "I like the complementary soda. The boarding groups system is smart."
Cons: "I don't care for the wifi options. Loud children."

Pros: "Excellent"

Pros: "On time"

Pros: "As pleasant as possible."
Cons: "Nothing negative to note."

Pros: "Attendant was attentive to her job."
Cons: "The aircraft is uncomfortable."

Pros: ".The attendant was caring and efficient."
Cons: "The boarding process seems to be a cluster of misguided sheep. The aircraft is uncomfortable even for us thinner patrons."

Cons: "The plane was just small and I'm a big guy."

Pros: "I was so comfortable and I got to sleep"

Cons: "Checked luggage took close to 45 mins to arrive"

Pros: "Great service. ...communicate with customers about changes at all times."

Pros: "Very friendly and great service. Gave us drinks twice."

Pros: "The service for wheel chair people was excellent"

Cons: "Late no place for my carryon"

Read more about JetBlue
COVID-19 information

Safety measures for airlines flying from Caribbean Islands to Chicago

Airlines flying from Caribbean Islands to Chicago 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 Caribbean Islands to Chicago

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Caribbean Islands to Chicago

Pre-flight testing

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

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