Find cheap flights from Chicago to Caribbean

Find cheap flights from Chicago to Caribbean

Round-trip
Economy
Chicago (CHI)
Caribbean
Fri 1/15
Fri 1/22
Any month
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Good to know

Low season

August Best time to beat the crowds with an average 6% drop in price.

High season

December Most popular time to fly with an average 9% increase in price.

Average price round-trip

$569 (avg. price over the last 2 weeks)

Good deal round-trip

$234 or less

Good deal one-way

$129 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 17% 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

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Top 5 airlines serving from Chicago to Caribbean

Scores according to KAYAK customer reviews

8.1
JetBlue
Overall score based on 19,351 reviews
8.3
Boarding
8.2
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews

Pros: "The crew"
Cons: "Everything good"

Pros: "Confortable seats"

Pros: "Fast boarding"
Cons: "Entertainment, comfort, food, crew politeness"

Cons: "They are advertising free movies and is not true, because once you're settled to watch the movie there is no headphones and If you want one they sell it, is not free."

Pros: "Short flight. Free movie was good."
Cons: "Flight attendant Christina (New York crew) did not like that I changed my mind about voluntarily checking my suitcase as there was plenty of room in the overhead compartment when I boarded. She said that the only reason I found room was because, by volunteering to check my bag, I was allowed early boarding. I corrected her by telling her that, no, I boarded early because I paid US$45 for an Extra Space seat. She made a face gesture and rolled her eyes. Very childish and unprofessional. She also seemed to have trouble reading the instructions clearly."

Pros: "Nothing"
Cons: "the flight was delayed 3 times and nobody could give us an explanation of what was happening, the customer service at the airport was extremely poor, informal and very very inefficient. I would like to know what the compensation will be for this unpleasant event."

Pros: "Cheerful, efficient service. No hidden costs. Free gate to gate WiFi. Comfortable seats. Never flown them before and they are now at the top of my list."
Cons: "Nothing yet."

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: "comfortable seats TV great beverages--actually get can or bottle"
Cons: "when we checked it, did not put us together"

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: "Food boxes for purchase are actually very good and probably well price"

Cons: "The flight was delayed and we would have missed our connection in NYC. So we had to cancel the trip."

Pros: "Great service, excellent snacks, the plane was new and new TVs, very comfy."
Cons: "Loved everything, thank you!"

Pros: "Good snacks, entertainment and excellent WiFi. Boarding was efficient and seats were comfortable."

Cons: "We arrived later for almost 2 hours"

Cons: "Delay flight"

Pros: "Per usual crew and plan itself were nice"
Cons: "Flight was delayed about 3 hours from scheduled take off"

Pros: "great service, friendly crew"
Cons: "none"

Pros: "The crew was friendly and courteous despite dealing with several young infants"
Cons: "No dislikes"

Pros: "Everything went smoothly...even boarded early."

Cons: "Plane was over an hour late"

Pros: "Great service"

Pros: "The flight was smooth and the crew was very friendly."
Cons: "Movie selection was very slim and could not get my seat to recline."

Cons: "my flight was delayed for 2 hours and there was no compensation for it"

Pros: "Very comfortable. Zero turbulence. Great crew."
Cons: "The lack of food options, but that is on every airline."

Pros: "Great flight awesome Crew"
Cons: "Cold lol"

Pros: "Very nice crew"

Cons: "Low variety of food and the fact that you have to pay for blankets, pillows and head sets"

Pros: "The crew was friendly and helpful as usual. There was a fair amount of leg room and overall space."
Cons: "One thing that has always made JetBlue stand out has been the customer service. I get pretty motion sick on flights, especially on an empty stomach, so the snacks and meals at mealtimes have always made this my favorite airline. There was none of that this time around. It feels like JetBlue is letting itself turn into just another commercial airline - over priced flights and amenities for overrated service and a lack of care for the consumer. Not to mention we were late"

Pros: "There was no entertainment on my leg from DC to SJU nor from SJU to STX. No power outlets for charging phone either"
Cons: "No entertainment nor power outlets"

Pros: "Nice employe"

Pros: "I appreciate Jet Blue's commitment to the people of Puerto Rico."

Pros: "A good Flight"
Cons: "TV was not function."

Pros: "From terminal to terminal the all jet blue experience is one of a kind. No other midsize airline for domastic flights provide the comfort and security as JB"
Cons: "Nothing"

Pros: "La cordialidad"
Cons: "La tv no funciono bien"

Pros: "The service"
Cons: "N/A"

Cons: "Service!!!!"

Cons: "Movies didn't work and we were one hour delayed on the runway."

Pros: "Crew worked hard to help us feel good"
Cons: "5 hours delay"

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: "Everything went smoothly!"

Pros: "Me encantó la gentileza de enviar correos electrónicos para mantenerme informada."

Pros: "Take off and landing was pretty good"
Cons: "Flight was delayed"

Pros: "Quick boarding process...good leg space"
Cons: "All was satisfactory"

Cons: "Flight delays."

Pros: "The crew was very attentive and accomadating. I travel with my daughter and her emotional support dog and they were understanding and made the trip easier for her. Thanks!!"
Cons: "The headphones should be complimentary and on flights of 3.5 hrs or more the snack should include a sandwich."

Cons: "My daughter was unable to use her tray table due to how dirty it was."

Pros: "I really enjoyed the in-flight FREE Wi-Fi, and the service was great! I will definately look for Jet Blue flights in the future"

Cons: "I couldn't breath well because the air conditoner, smell bad, loud crew and because of that I couldn't sleep and I was very tire."

Pros: "Good"
Cons: "Good service"

Pros: "The food"
Cons: "Everything ok"

Cons: "The gluten free food, I was food poisoned with it! It was horrible! Use better airplanes, the movie was ok but the system is old."

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"

Pros: "excellent service"

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: "Everything. They try so hard to accommodate regardless of class."
Cons: "Planes are equipped with old entertainment screens. Not a big deal though as you bring your own entertainment now a days."

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!"

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: "Service was excellent"

Pros: "Es la Primera vez qué vuelo con Uds. Me gusto La amabilidad del personal. Sigan así no cambien."
Cons: "Uds deberían llamar primero a Los grupos finales, ejemplo 5 ó 6 para evitar incomodidades por el pasillo."

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: "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: "Food was ok"
Cons: "No WiFi, no outlets, no entertainment for international flights seems very outdated."

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."

Pros: "Service"
Cons: "The business class was empty and Copa did not offer an upgrade."

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: "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."

Cons: "Flight was overbooked and I got bumped. Needs to be ther for work very inconvienant"

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: "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."

Pros: "nothing"
Cons: "custumer service"

Cons: "This trip was 1st time using Copa airlines. They misplaced my bag on the way to Bogotá and I didn't receive it until 3 days later."

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: "I love flying Copa! My friend and I had only a 40 minute layover on Tuesday morning from San Jose, CR to Panama City to Chicago. We were pretty worried about missing the flight in Panama City because that meant we missed our fight home. The crew was wonderful and changed our seats to the front of the plane so we wouldn't miss the flight. If he hadn't had done that, we 100% would have missed the flight .I will recommend Copa to everyone."

Pros: "They had a vegetarian pasta option and the crew is always friendly!!!!"
Cons: "We were an hour late arriving. Boarding was slow."

Pros: "Food and drinks."
Cons: "Bad entertainment selection and screen."

Cons: "I was forced/tricked to check my instrument on the boarding gate when what i really asked for is for the crew to take it o tha plane or for them to let me take it on carry on. Someone lied to me and then they checked in with the loggage"

Cons: "Not enough smiling from the crew"

Pros: "Cheapest flight to Cyprus"
Cons: "Dirty, cramped, and they neglected to send my luggage on from Amman."

Pros: "Exit row seat very roomy with plenty of leg room."
Cons: "Flight from ORD to LGA delayed even though the plane was already at the gate in ORD. No announcement explaining why it was delayed. What was worse was that after landing at LGA, baggage tagged as Priority did not come out first, it came out much later - after numerous non-priority baggage came out. This is not the first time this has happened at LGA. What's the point of tagging it as Priority if it won't be handled that way?"

Cons: "This agent spent 30+ min to check us in through a connection flight to Seattle. He couldn't find my wife's reservation, when it should be in the same reservation as me. He tried 5 times, and still failed. Later we found out at the gate that he was using the wrong name (same last name, different first name). Luckily the American Airline agent at the gate was more than competent and efficient to correct the issue in 5 min."

Pros: "Arrived early, friendly crew, good exit row seat."

Cons: "Horrible delays. Delta doesn't have these problems."

Pros: "Always delayed. Always check my carry on. Which equals me being late to where I'm going."
Cons: "See above"

Pros: "The plane left on time"
Cons: "Attitude of personnel on plane Plane was old and in need of up grading No service, you have to ask for a cup of coffee and they give it to you as it is a favor Keep inventing reasons to make it more difficult to achieve any level. They invented a platinum """""Pro""" level that used to be Platinum and downgraded the platinum level so they provide less perks"

Pros: "Food was decent, service was okay"

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: "Crew was very nice. Free snacks provided on plane."

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!"

Cons: "Surprisingly, AA provided the worst experience of the overall itinerary, compared to Aer Lingus and Iberia. The AA plane was outdated, cramped legroom - despite having purchased an "upgraded seat" and departed 1hr late"

Pros: "on time"
Cons: "very cold"

Cons: "The entertainment system in my seat was broken. Was a bummer since we added a extra hour ground hold for weather."

Pros: "Once I made it, they worked to get me on the plane from Chicago quickly."
Cons: "I barely made it for my flight in Chicago and that was with running. They were already boarding the other plane when my plane from Hattiesburg landed. Earlier in the day I had to get them to change my flight from Chicago in Hattiesburg because it wasn't changed for me when the delay had my original flight leaving before I was to land in Chicago. I don't fault them for someone getting sick at the last minute or my inconvenience, but it was still inconvenient."

Cons: "Tsa is very unorganized and extremely rude."

Pros: "In flight movie options are great!"
Cons: "We boarded about an hour late but that happens."

Pros: "NOT much!"
Cons: "My window seat was right against the right engine. I could feel the vibrations and noise. It seemed like an old plane. I was definitely miserable on this flight. Very!"

Pros: "I appreciated the American Airlines crew at the gate in Chicago, who helped us to get two seats together. The flight crew was excellent as well."
Cons: "Not being able to choose our seats beforehand."

Cons: "it was an hour late"

Pros: "Was listed on-time up to 20 minutes before boarding. Then the departure time kept getting pushed back until we departed two hours late"
Cons: "If there is a delay, I'd rather them just be up front in estimating the time of the delay."

Pros: "In your Chicago office. He was extremely helpful both to us (too older ladies) and to others. Please thank him for us and look at him for a promotion. I think he may work for American Airlines instead of British Airways."

Pros: "First class flight attendant was awesome!!"

Pros: "Actually, I like that it was late because my first flight arrived late. The flight overall was very quick and smooth."
Cons: "The seats were covered in crumbs from the previous flight, but that's probably because of the hurry to get passengers on to the next flight because the plane was late."

Pros: "Arrived early"
Cons: "Overweight flight attendant bumped into me everytime they went down the aisle making sleep very difficult."

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: "We boarded on time and arrived early. What more can ya ask for? Fairly easy ride. Free entertainment on board, movies and shows! Awesome."
Cons: "The speaker that the pilot used was static-y, hard to understand. No free wifi option. Rough landing."

Pros: "Staff was very nice; very courteous."
Cons: "We were delayed for 2 hours! I had a premium seat but still ended up boarding with Group 6. Almost ran out of room and had to check my roller. Not happy with late boarding given that when I booked my ticket, it said I'd have priority seating."

Pros: "All connections-smooth"

Pros: "We did not take this flight when its schedule was moved back, instead taking one LHR-SEA that would get us home at a reasonable hour."
Cons: "The change by British Air in flight departure/arrival times. The resulting adjustment was costly and we were unable to get "extra" seating on the long leg of the trip by the time we were notified of the changes."

Pros: "More options for entertainment on a long flight."

Cons: "one of the worst trip ever. although there were many turbulances, the captain did not appear to be proficient along the way. The landing was horrible as well."

Cons: "Ground crew was inadequate and unorganized. Ground crew caused a late flight to be even later. Plane was overbooked and the ground crew was more interested in filling the flight than accommodating Advantage Member seating."

Pros: "When we arrived, we found the plane was changed, and our seats were in the middle, and separated. We had paid extra to have window seats.. After speaking to one of the gate attendant ( Arturo ), he went out of his way to accommodate us, and we ended up with great seats. Friendly and accommodating crew! ."

Pros: "worst experience. Airplane people not so good"

Pros: "The crew was courteous and very nice."
Cons: "The aisles are too narrow. As passengers are boarding and you sit in the aisles you are constantly struck. FAA should investigate with the decreased aisle width and distance between the seats, can the evacuation be completed within required time, in an actual emergency. American Airlines is endangering the lives of passengers. And the cramped conditions are contributing to the hostile actions of some passengers. What does it take to do what is right?"

Cons: "Forced to check my carry on. Took 30min for the bags to come out on the carousel. Which is why i never check my bag."

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."

Cons: "I took the bus from Ohare to Gen Mitchell airport because of delay at Ohare. No crew, again."

Cons: "Lovely flight, but onboarding groups were a nightmare. Given the chaos, they started forcing bags to be checked early."

Pros: "Friendly crew"
Cons: "3 hour delay"

Pros: "Exit row seating."

Pros: "No individual screens to watch. Get with the times for long flights !"

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: "Flight was straightforward and crew were pleasant."
Cons: "The boarding process was not so good. It was a busy flight and they needed to put luggage underneath asking for volunteer, then after a certain point it was mandatory. I completely appreciate the need for it to happen, but it turned into caos. People everywhere stood waiting. My suggestion would be to have people who need to check baggage stand off to the side and continue boarding those who are ready to go."

Pros: "Ok flight"
Cons: "Not iberia"

Cons: "I was unable to get this flight and rebooked onto a United flight that was denatured 4 hours."

Cons: "Return flight was delayed, gate changes unfriendly and unhelpful flight attendants"

Pros: "Nothing"
Cons: "Thought it was funny I didn't get a survey about my disaster trying to leave Boston, only the on time flight getting back. 6 hour delay leaving because of a warning light they didn't catch to begin with. Missed a whole day of vaca. No help once they deplaned us. Horrible flight. First time on American too. Paid for a window seat specific and had no window."

Pros: "Boarded plane on time"
Cons: "Plane looked old and beat up. Sat in plane at jetway for a 45 minute maintenance delay."

Cons: "Free WiFi kn the plane was hardly working even over US mainland, before it list connection with outside internet over ocean. But it is something I do not care much about."

Cons: "We reserved wheelchair assistance prior to the flight. We had to wait an extended amount of time to actually get the wheelchair assistance with 5 kids 7 and under. Due to the wait we almost missed our flight, we were literally the last to board the plane. We were hoping to grab some breakfast for the kids as we had a long flight and did not have time to do so because of this delay. This is why we called ahead to reserve the wheelchair. The people checking in did not seem to care about the delay and only told us to be patient. Sad, unfortunate experience with accessibility issues."

Cons: "While going inside the flight they told me there is no room for Carryon and gave me ticket to book the luggage. When I went inside the Flight there is lot of room to carryon's, why they have to lie this BS."

Cons: "The crew no food no pillow no blanket"

Pros: "We'll coordinated."

Pros: "I liked the Lufthansa flights using Airbus Aircraft the entertainment system is the best."
Cons: "The entertainment system on the boeing planes is not necessarily the best, the screens are smaller, the selection of movies is not upto date and even Live TV does not work"

Cons: "See above comments."

Pros: "In flight entertainment was great!"

Pros: "The comfy seats"
Cons: "The fact that I had to pay to watch tv. Maybe people should have to pay for movies, but not for watching tv. Flights and till we takeoff can take a while. It would be nice to have some free entertainment. The plane was very hot when we were boarding."

Pros: "Seat to myself"
Cons: "Lil bumpy but there were a lot of clouds"

Cons: "The seats are tiny. If you drio something, you can't reach down to pick it up. The food was burnt. The app isn't downloadable in China. The overall experience makes me not want to ever fly United again."

Cons: "Entertainment and food could have been better."

Pros: "Excellent as expected."

Pros: "Good entertainment for a long flight."
Cons: "A power jack could come handing."

Pros: "United got me from point A to point B"
Cons: "Crew was rude, not just to me, but to other patrons. Flight was packed going and the man scanning boarding passes spoke to those of us asking simple questions as if we were stupid and defiant. Was he a prison guard in his previous job? On the way to Newark, I had an aisle seat. One of the stewardesses blazed by me with a cart ramming it into my shoulder without so much as a, "sorry." I'm not a big woman but maybe as I dozed off I leaned over a bit...There is no way she didn't feel her cart hit me. Rudeness, it seems is a part of the culture at United because the flight attendants coming back squeezed past the long line for the bathroom without saying, "excuse me." They did however, say, "I need to get by," and one of them brushed by the gentlemen sitting next to me and bumped his laptop and coffee. Overall it seems that the crew working these particular United flights have forgotten that we pay hard earned money to fly. Some of us are going on vacation, to see loved ones, and some are flying to deal with unpleasant circumstances. The staff may fly several times a day, but most passengers do not. There's a lot of prep and anxiety, that goes into taking a flight and a surly flight crew multiplies that anxiety. No one wants to fly with a crew that hates their job."

Pros: "The flight overall was great, easy to board and de-board, and a smooth process from start to finish."
Cons: "Connecting to the in-flight wi-fi to watch movies and tv shows was nearly impossible."

Pros: "Loved that it was an empty flight"

Pros: "The service was good"

Pros: "Friendly flight attendants, helpful staff at the ticket counter."
Cons: "Unable to check into both legs of my flight even though Air Canada used United for the first leg."

Cons: "Two hour delay for start of engines.. Not enough chichen and pasta was not good"

Pros: "The flight was a head of schedule and very smooth."
Cons: "It was freezing cold. I was wearing a sweater and was freezing."

Pros: "I have metal leg braces. The staff was helpful getting me from terminal to terminal. They were very helpful."
Cons: "Having a leg brace makes difficult I am blessed I can move a little without them. I had to move a short distance without my brace. No place to put it back on."

Cons: "i missed my flight because my flight left Toronto late"

Pros: "Pilot was very happy and friendly! Very informative throughout flight."
Cons: "On the return home, I was seated in the last row right next to the lavatory. I was bumped into at least 40 times by other passengers and flight attendants."

Pros: "not a damn thing"
Cons: "Weather delays are a typical part of travel. What's not typical are 5+ hour delays and sitting on the tarmac and watching your connection take off without you. First Class seats morphed into Economy center seats the next day, with nary a hotel room in sight. Thanks for nothing."

Pros: "The flight was on time."

Cons: "The flight was very hot and uncomfortable!"

Pros: "Nothing"
Cons: "This flight never happened it continued to get canceled and canceled!!"

Cons: "seats were very uncomfortable"

Cons: "We got on board, waited 20 minutes. Capt said it was a bad reverser, and we were waiting on paperwork for 15 minutes. Long story short, they make us leave the plane after 2.5 hours. Then we wait in the airport for another 2.5 hours. I missed my connection and spent 10 hours in Chicago."

Pros: "The flight attendant finally took care of it after I complained a couple of times."
Cons: "That you changed our seats, and, that there was no room in any of the overhead bins. So, the flight attendant told me that I needed to fight my way through the people coming toward me back up the aisle and check every overhead bin all the way back up to see if there was room for my one suitcase. Others had brought more than one bag up there. Finally they checked my one carry on bag. The ride was also really bumpy, worst that we've ever experienced. But that was due to weather conditions."

Cons: "Everything! Even worse than my previous flight. Delays were inexcusable, staff ridiculously unfriendly and just bad attitudes all round. Very unpleasant experience, won't be using this airline ever again."

Pros: "Nice clean plane, very friendly and helpful crew."
Cons: "The hour delay."

Pros: "The crew was fantastic despite the entertainment system wasn't working"
Cons: "The entertainment and wifi was nonfunctional for the 8 hr flight."

Pros: "Pre-check with United"
Cons: "Did not get connecting flights boarding pass from the beginning. Short connection time - was very stressful"

Cons: "Couldn't reserve/request a seat. Assigned to me About 1.5 hours prior to boarding. Had to wait Around the gate. Should have told me I would not have any choice. Could have walked around. Got a middle seat. It was a long flight."

Pros: "The flight attendant was great! Pleasant, polite and professional!"
Cons: "The flight from ORD to ABE was on a plane with expired maintenance logs or inspections? We were delayed 2 hours in arriving for what seemed like a pilots lax in paperwork. But what does a customer expect from an airline who knows they that customer by the balls?"

Pros: "Great boarding at ORD."
Cons: "My seat"

Pros: "Movie selection and delivery/access was very good"
Cons: "Seat legroom is insufficient. There was a water leak in the ceiling that dripped cold Wster on me for a portion of the trip."

Cons: "The flight was late by 5 hrs due to mechanical problems. The gate crew was confused about what to do and we ended up with several deboardings and boardings. Food was terrible. The entertainment system did not work."

Pros: "Everything else was fine"
Cons: "For such a long flight and quite expensive some food should be provided. I have never flown before like that (over hundreds of overseas flights) and had NO FOOD given at all."

Pros: "the flight attendant crew was super nice throughout the entire flight."
Cons: "the tvs weren't working for the all the seats, and the food was not very tasty."

Pros: "Flight itself was good. Nice flight attendants. Funny pilot."
Cons: "The lady at desk to board the flight made me check my carry on. I had assumed it was because the plane was full, but when I got on the plane there were more than adequate spots to stow more bags. There was a compartment across from my seat that remained open the entire flight. While I completely understand the need to check extra luggage when the plane is full, I was very upset when I saw it was not. I intentionally fly with a carry on for the convenience, and to be inconvenienced for absolutely no reason made me not want to fly with this company again for fear it could happen again in the future."

Pros: "The flight crew was very helpful and organised the connection between two flights very well under pressing circumstances when there was only 15 min between the flights and the boarding gates being in opposite ends of a big Munic airport"
Cons: "The flight was delayed for 2 h, so we had to run through Munic airport for connected flight. Good sport, but rather tiresome."

Cons: "8 channels of looped shows and movies. Too long a flight for that...and then have to use my device to watch on the free part of the wifi.so no battery left. For this price? And I booked through Lufthansa but flew United. Bad form."

Cons: "The plane was tiny and the seats were tiny. Could not carry on a bag and it took a long time to get the bag back from having been gate checked."

Pros: "the japanese speaking flight attendant was exellent! she was very observant to passengers needs. i was also pleasantly surprised by the entertainment system."
Cons: "there was a flight delay due to maintenance, which was inconvenient."

Pros: "The trip had minimal turbulence. The landing was smooth."
Cons: "-The 767 was old. -It did not have any power ports for my laptop or cell phone. -The interior was old and dated, reminiscent of the 1980's. -The TV screen for entertainment seemed to be smaller than a Samsung Note 5. -The seats are unreasonably narrow and not comfortable. -I had an isle seat and my shoulder width is literally wider than the seats. -Every time the isle cart went by, it hit my left shoulder. -The seats in general seating are too small and were cramped. -God forbid if we had to egress out of the plane. -There were no adjustable head rests, like other airlines have. -The Flight Attendant for my section DID NOT make me feel like I was a valued customer, even though I paid over $1500 for flight. -She scolded me for asking "Why," when she TOLD me that I needed to sit in one seat, even though the seat next to me was vacant. She literally treated me like a child. - NOT COOL. Overall, in comparison to my last international flight, I WOULD NOT recommend United. I feel like I paid too much for my experience with United. Aer Lingus has better/newer aircraft, better cabin crew, better entertainment selections to include music and a selection of movies to watch at your convenience, more comfortable seats, provide a better environment, and a better value for your experience. Aer Lingus was also cheaper. So if you are reading this, please shop around if you are considering United to fly."

Pros: "Flight left on time crew friendly and attentive"
Cons: "Long flight could not get a diabetic meal !"

Cons: "It was delayed so I had to take another flight. I've been trying to get this flight refunded"

Pros: "service,crue,flight"
Cons: "Flight was delayed 4 hours for departure.I am a member of Team USA and was on my way to OTC for TEAM PRACTICE getting ready for Panamericans in Santo Domingo.Arriving late caused a series of events that cost me a lot of money.I missed the athletes bus by being late and had to take a taxi.I missed the morning and afternoon practice due to the plane delay ,which was so important to me.The first day of training out of the 7 scheduled was waisted.I can not afford to lose time and money in that manner,therefore I will think twice before I risk another flight with Frontier."

Cons: "Arrival seemed uncoordinated and didn't have a dedicated terminal gate."

Pros: "Fast boarding and that's the only good quality. No refreshments or snacks offered without a price tag included. Seats don't recline. Uncomfortable hard seats without any head rests for Support. Small tray tables that won't hold a laptop or drink."
Cons: "It's been 45+ minutes after landing that we have been stuck on the runway unable to dock the plane due to some delays. How Terrible is it that the pilot gets on the radio to say he has no updates or much information to give! People are antsy, children crying and this delays all passengers with other accommodations. Seems like there's no communication or organization from Frontier at all!!'"

Pros: "Getting off the plane"
Cons: "Being in the plane"

Cons: "Staff was rude was not comfortable seating"

Pros: "N/A"
Cons: "I arrived 20 mins before departure and from front desk agents would not issue a boarding pass because they said they were already boarding and I wouldn't make it to the gate. Their only solution given to me was to fly to Denver the next day for a layover and fly out to my final destination the next day after that. I was encouraged to find another airline too."

Pros: "Fast boarding."
Cons: "Staff was rude. Seats uncomfortable. Sat on the runway for 30 minutes because we we're a half hour early."

Pros: "Quick boarding and great comfortable ride, awesome flight attendance!"
Cons: "No complimentary snacks nor tv"

Pros: "Offering a direct flight from COS"
Cons: "Outrageous charge for checked bag"

Pros: "Everything except the passenger who was drunk"
Cons: "The fact they allow him to answer the plane when he cannot stand on his feet"

Pros: "Nice crew"

Pros: "Best Frontier experience I've had in a long time. Everything was very good and despite a delay getting the plane to the gate in Chicago, we were able to make up almost all of the time!"

Cons: "Additional costs for selecting a seat and carrying on a bag that was not readily apparent when the flight was originally booked, but added $50+ to the overall cost of the flight. In addition, I experienced a 2+ hour delay on my flight from Chicago to LAX on a Sunday evening, which soured the comfortable end to my weekend travel experience."

Pros: "The crew were pleasant and helpful."
Cons: "Delayed 3 times. Didn't get to my destination until 1:30 am. 5 hours later than expected. I don't think I'll fly frontier again."

Pros: "Everyone was very nice, the seats were roomie!"
Cons: "Everything was good!"

Cons: "They didn't tell us they stop issuing tickets 45 minutes before departure."

Pros: "O'hare airport."
Cons: "I was unable to print a boarding pass at one of the many kiosks - it informed me I needed to speak with a Frontier agent. The line for the agents was about 2 hours long, too long to wait to make the flight. After being told by a frontier employee that I'd just want to get in to the line to rebook on a later flight (9 hours later) I proceeded to speak with a momentarily vacant agent who, helpfully, printed and handed me my boarding pass. I arrived at the gate to a closed door and ended up needing to rebook anyway. I decided to just not go on the trip.... wasn't worth having to deal with Frontier 2 times in one day."

Pros: "For less than two tanks of gas, I flew from RDU to Chicago and back. It's a no frills airline, but everyone was nice, and I got where I was going on time. Can't really ask for more than that."

Pros: "Flight was on time, boarding was quick."
Cons: "They charged to pick seating, for carry-ons, and for beverages on the flight. The money I "saved" compared to other airlines, I ended up probably spending more due to the additional charges."

Cons: "Seats are not conftable"

Pros: "Crew service"
Cons: "Free drinks and Snacks weren't provided"

Pros: "Boarding was easy. On time departure and on time arrival."
Cons: "Short flight so no food or entertainment. Initially crew said would be coming with cart with complimentary beverages and then they said they weren't but you could buy items."

Pros: "On time, friendly and affordable prices"
Cons: "Not very clean, the airplane was messy"

Cons: "It was a terrible experience in my life. A Frontier female worker who was working at O'Hare international airport between 4pm and 5pm was really rude. There was a problem in my barcode so I asked how I could solve the problem. When I first went there, she said "no" and she started to ignore me by not answering. I almost missed the flight. And when I went there twice, the woman hided under the counter after seeing me. I was shocked. The worker at Frontier was never professional and acted like a child. The service was terrible. I would feel okay if she could try to help me not to miss the flight. Instead, she had no willing to help me, and sneered me. I missed the flight so I had to buy a new flight ticket. I'll NEVER use Frontier anymore, and I'll recommend to people not to take Frontier. Workers' service is the representative of the company, and she was terrible."

Pros: "The over all experience"

Pros: "The price of the ticket"
Cons: "The seats were awful, no padding what so ever!!!!"

Cons: "Flight home was 30 minutes late and not one rep apologized or updated passengers. Horrible communication."

Cons: "3 HR unknown delay"

Pros: "Easy boarding easy check in"
Cons: "Nothing that bad, chairs are maybe a bit thin but not terribly uncomfortable"

Cons: "Cabin was pretty dirty and not well managed."

Pros: "price"
Cons: "seats are hard. the time on the ticket was not changed for the time zones so we waited to get to gate"

Pros: "Speedy boarding and fast flight, crew was ok."
Cons: "Charged for one bag, charged for soda and chips on plane."

Pros: "Price of the flight was great, but there are hidden fees."
Cons: "Having to pay for carry on and seats aren't comfortable"

Pros: "The crew was nice and fun"

Cons: "The web site is deceiving in that it makes you think every seat is an upgrade and no regular seats remain. A distinct "no upgrade" choice needs to be present for people to see. It makes one think, how much money Frontier has made from people due to their purposeful website's lack of clarity. This is pretty pathetic."

Pros: "Great prices and way better flight experience than I was expecting after reading other reviews. Seats don't recline but are still comfortable."
Cons: "Flight was delayed and no updates were given. Upon arrival, our checked bags took an hour to get to the carousel. Again, no updates at all."

Pros: "No problems went very well"
Cons: "Nothing bad to say"

Pros: "Non- Stop flight"
Cons: "6 hour 15 minute delay due to a mechanical problem. I learned that the problem was a broken seatbelt. I later learned that this plane was in the hanger in Chicago since the previous night. I received a $100 voucher for the inconvenience. I have to use the voucher in 90 days. Since I am not a frequent flyer this is no use to me,it should be extended to one year."

Pros: "Easy quick boarding"
Cons: "No entertainment or courtesy drinks on the flight"

Pros: "When it was over."
Cons: "A four hour delay with no explanation. Giving up my seat so a family could sit together, only to be told I might have to get off the flight because they were over sold. Complete lack of professionalism."

Cons: "plane 2 hours late. They charge for everything-even your seat"

Pros: "Boarding was easy due to being able to pay for a seat ahead of time."
Cons: "The flight attendant was cranky and I was shocked when I asked for a bag of peanuts and she said that I would have to pay for them. Not even a stale soda is offered. You have to pay for everything. I will pay for Southwest next time. The flight, after all the extra charges, was more expensive than the Southwest flight. I am very disappointed."

Pros: "Everything from start to finish was great. Professional crew, on-time, painless boarding. I'm a fan!"

Pros: "The flight was on time despite the Chicago snows. The gate staff and onboard flight staff were friendly and professional."

Pros: "Courteous crew."
Cons: "Gate change at last minute. Had to wait for plane to get to gate. 1 hour late. Another 45 minutes waiting for de-iceing but that not their fault. Will not use this airline again."

Cons: "You get what you pay for. I will pay for better service next time. I'm not a tall person I and I felt cramped in the seats. There was no in flight movie. It was a 4 hour flight. With all the add ons my ticket ended up being the same price as the other airlines. I will never fly frontier again."

Pros: "The flights were great. Left on time and arrived early!"
Cons: "Nothing"

Pros: "It's so nice to not be bombarded by mircrowave radiation durint the flight, thank you for not having wi-fi onboard, we appreciate it!"
Cons: "Seats could be more comfortable"

Pros: "Good flight"
Cons: "Just remember, you get what you pay for. My flight was $148 from Denver to Chicago on Frontier."

Pros: "It was very punctual"

Read more about JetBlue
COVID-19 information

Safety measures for airlines flying from Chicago to Caribbean

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

Heightened sanitation

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

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Chicago to Caribbean

Pre-flight testing

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

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