Find cheap flights from Chicago O'Hare Airport to Caribbean

Find cheap flights from Chicago O'Hare Airport to Caribbean

Round-trip
Economy
Chicago (ORD)
Caribbean
Fri 1/22
Fri 1/29
Any month
Compare vs. KAYAK |
Search hundreds of travel sites at once for deals on flights to Caribbean

Good to know

Low season

August Best time to beat the crowds with an average 5% drop in price.

High season

December Most popular time to fly with an average 16% increase in price.

Average price round-trip

$567 (avg. price over the last 2 weeks)

Good deal round-trip

$258 or less

Good deal one-way

$122 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 14% 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

Which airlines have a flexible cancellation policy for flights from Chicago O'Hare Intl to Caribbean due to COVID-19?

Which airlines apply social distancing measures on flights from Chicago O'Hare Intl to Caribbean due to COVID-19?

How long is the flight to Caribbean from Chicago O'Hare Intl?

How does KAYAK find such low prices on flights to Caribbean?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Caribbean?

What is the Hacker Fare option on flights to Caribbean?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Caribbean?

Top 5 airlines serving Chicago O'Hare Intl to Caribbean

Scores according to KAYAK customer reviews

8.1
JetBlue
Overall score based on 19,354 reviews
8.3
Boarding
8.2
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews

Cons: "This flight was very delayed"

Pros: "Free wireless"
Cons: "I'm not in Charlotte"

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: "Ease of checkin."
Cons: "Delayed by 2 hours."

Cons: "My first flight was delayed an hour due to pilot error (we left the gate on time, but sat on the tarmac for an hour). This caused me to miss my connecting flight, which stranded me at JFK because they only had one flight per day to my destination. JetBlue's customer service told me I could not reach my destination until the next day, which was unacceptable (I had a morning interview). In fact, the only thing they said they could do was *PARTIALLY* refund my ticket, even though they stranded me in a completely different city. They also said I would "be able to" book a new flight with a different carrier, which cost roughly $400, using my own money. In the end, I spent about an hour talking with customer service until they were "nice enough" to do a partial refund with an additional credit equaling the remainder of my $400 ticket to fly with them in the future. It was still a very poor interaction with customer service."

Cons: "2 hours late!"

Pros: "I love the fast service, and the willingness of the staff to help customers onto the flight. I loved the snacks and variety of drinks JETBLUE offered whilst on the airplane. The team on flight 421 was superb. They were courteous, knowledgeable, very accommodating in particular the steward by the name of TONY."
Cons: "Everything from start to finish, from check in to departure was excellent."

Pros: "Clean plane"
Cons: "Took 3+ hours to get in the plane"

Cons: "The cabin crew was a little lacking and the captain did not mentioned that we had landed almost a full hour later than scheduled."

Pros: "Pilot’s smooth take off and landing."
Cons: "The weather haha."

Pros: "I liked that the pilot was able to make up some time because our flight was delayed over one hour in Chicago."
Cons: "The notification that the flight was boarding early. I enabled notifications and still did not receive notification that the plane was boarding."

Pros: "Nothing"
Cons: "Being delayed from 6am to 1:30pm"

Pros: "Flight was delayed 30 minutes at takeoff but landed when it was scheduled, so it was fine. Flight attendants didn’t make you stay in your seat, so you could use the lavatory. A fine, uneventful flight. Free WiFi. Snacks. Drinks. Fairly comfortable seats with decent legroom."
Cons: "Wish the seats in front of the emergency exit reclined."

Pros: "The crew was unfailing cheerful and helpful. The seats are comfortable and there’s a little more space than some airlines. The fight and particularly the landing was very smooth. Great experience!"

Pros: "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: "Nothing!"
Cons: "IT WAS TWO BOURS LATE!"

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: "The crews were very friendly A lot of options from direct tv and other entertainment programs The seats were wide enough Free Wifi"
Cons: "The plane got 2 hours delayed The screen was too small There was no charger on the plane Food option was limited"

Pros: "Entertainment, food, crew, and cleanliness were 100000% on point. Loved it."
Cons: "Turbulence and the flight was longer than necessary because we had to go around bad weather. Not the fault of JetBlue!"

Pros: "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: "Seats were pretty comfortable with decent legroom."
Cons: "Plane was freezing cold, but a blanket had to be purchased."

Cons: "We arrived later for almost 2 hours"

Pros: "I dont usually fly, staff was friendly and helpful, made my experience less stressful."

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

Pros: "Our flight attendant Jeramy was FABULOUS!!"

Cons: "No movies just Direct TV."

Pros: "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: "Smooth flight"
Cons: "Tvs were off for the entire flight, and no explanation."

Pros: "Extra leg room"
Cons: "On both legs of our vacation, going and coming we experienced long delays , 2 hours Boston.to Vhicago and 3 hours Chicago to Boston"

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: "L.L Bean crew was amazing!! The tv channels and movies!!"

Pros: "I appreciated the fact that we didn't take off until the weather was clear and it was safe to fly. I am glad that they were concerned about our safety."

Pros: "the plane was good!"
Cons: "the plane boarded late"

Pros: "Surprisingly good leg-room. Comfortable seats."
Cons: "We had some mechanical issues that delayed us, but we arrived on time. So it turned out fine."

Pros: "Everything."

Pros: "Entertainment"
Cons: "Flight was delay. Long waiting on the runway for takeoff."

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: "Everything was great. Easy boarding great comfortable seating and friendly efficient stewardship"

Cons: "Boarding was a little chaotic. Could have been more organized."

Pros: "staff was amazing, entertainment great, dasani sparkling lime water tasty, very clean and reasonably comfortable"
Cons: "the breakfast was made of 90% sugar - this was very disappointing."

Pros: "Everything was on time!"

Cons: "The flight was cancelled. I didn't receive a refund or free hotel accommodations. I've been on flights in Africa where free hotel accommodations were standard for a layover over 3 hours. A little embarrassing that an airline in America can't afford a hotel for people stranded in a city overnight."

Pros: "I got the vegetarian meal I asked for."
Cons: "Flight was delayed, because of the boarding process with immigration"

Pros: "This flight left about 90 minutes late again due to weather issues. The crew was excellent which made this long flight enjoyable."

Pros: "Staff extremely friendly and helpful"
Cons: "Old plane with no individual tv screens!!! Didn't know these planes still existed!"

Pros: "Extra blanket and pillow. Empty seat to sleep in. Fairly clean interior for the most part."

Pros: "Flight attendants were nice"
Cons: "The seats were incredibly uncomfortable. There was no leg room and 122 of the space below the seat in front of me was taken up by a metal box attached to the seat. I couldn't put both feet under the seat in front of me. The food was bad tasting and overly processed. We were fed a lean cuisine. The entertainment was from mounted tv's in the aisle. At this point, all planes crossing the ocean should have individual tvs for a customer to watch. They had this 15 years ago, how do they not have it now."

Pros: "Flights lately have been a huge disappointment but American Airlines was great! Crew was so pleasant and helpful,food was good and the "entertainment" was too! I'll definitely fly with them again!"

Pros: "All good! Nice staff. Easy travel."

Pros: "The crew was very efficient and friendly while handling everyone. Flight was smooth, food was good. I went to the wrong terminal and did not know that the advertised finair flight was actually American Airlines, the AA ticket counter attendant went all out to make sure I made it to the gate. All this with less than an hour before departure."
Cons: "I went to the wrong terminal, the email ticket had finair in large print and in smaller print indicated American. Luckily I was able to literally run and make my flight. Would be better to more clearly indicate actual airline."

Cons: "Small seats, no wifi, no chargers, terrible entertainment."

Pros: "Once we got on the plane, everything was pretty standard"
Cons: "Flight was delayed 5 hours."

Pros: "The water was clean"
Cons: "Everything else! We were first sold a British airlines flight, and then we got switched to American Airlines. I don't know if that is actually an okay thing for them to do. When we got onto to plane we were stuck on the runway for over 2 1/2 hours, where the outside temperature was 95 degrees and the AC in the plane didn't work. The delay was all due to a mechanical difficulty with the engine, this did not give us peace of mind when flying over the atlantic. while up in the air my newly wedded wife and I were hoping maybe we could watch a movie to help keep our minds off the creaking of the wings, the pool of sweat from the delay, and the grumpy flight attendants. Seeing as it was a 9 hour international flight, you would have expected some sort of entertainment. Maybe a personal TV.... nope. Maybe a community TV... nope. At least they have to have a radio....... nope. All we got were our two thumbs to twiddle. After a much needed nap. We woke up hoping maybe for a hot breakfast, but to put the cherry on top of some terrible ice cream, we got a mediocre cold breakfast. All in all I will not fly American Airlines again. I would happily and quickly pay double for any other airlines but them. It's such a poor reprisentation of our country."

Cons: "Old plane with no plug-ins and outdated media."

Pros: "Staff on the plane were nice."
Cons: "5 hour delay, fear of cancellation ruining a trip planned for years, not feeling we were told what was happening, series of delays extending decision time, unappetizing sandwiches during delay."

Pros: "Free alcohol and good passenger friends and friendly service."
Cons: "No outlets for phones"

Pros: "All the movies"
Cons: "Legroom"

Cons: "Could not read paper when passenger in front reclined seat. No space between rows."

Cons: "My flight was actually processed under American Airlines. Oddly, the confirmation email stated it was Finnair."

Pros: "On time"
Cons: "Cramped seats. Entertainment system outdated"

Cons: "Plane was too old, flight attendants were rude"

Pros: "The departure time. This left enough time to get to the airport and go through security without rushing!"
Cons: "Sitting in the middle Paying for luggage ( I wish Southwest flew out of ORD)"

Cons: "No complaints."

Cons: "Boarding seemed extremely unorganized. Crew skipped group 2 when calling groups to board, resulting in a mad rush."

Cons: "Due to two flight delays, I traveled an additional 24 hours, on top of my 20 hour original flight. Albuquerque Airline staff were rude, dismissive, incompetent, and each individual I spoke with gave me wildly differing information. The two delays (leading to approximately 48 hours of travel) would have been stressful enough, but the callous, ignorant and unprofessional attitudes of American Airlines staff (and staff in general at Chicago O'Hare Airport) really disappointed me. This was even more striking compared with the professional service I received from British Airways (from whom I purchased the tickets). I was ashamed that my country could lag so far behind in terms of basic customer service and problem solving."

Cons: "Requested for wheelchair assistance but none provided?!!"

Pros: "Timing and transit time was excellent"

Pros: "Everything."
Cons: "Nothing."

Cons: "Food was horribe and no dedicated tv per seat"

Cons: "We were delayed for 6 hours due to a maintenance issue. Horrible customer service"

Cons: "Always a problem with these guys"

Pros: "Couldn't of been more impressed especially after being hung out by Southwest!!!"

Cons: "We have flown to Europe recently on SAS and that airline was so much more comfortable than airberlin. Things we missed: personal TVs on the seats, good leg room (airberlin was quite cramped), and small attentions like a disposable towelette. I got no sleep on airberlin."

Pros: "Staff was very friendly and helpful"
Cons: "Experienced 4 hour delay with mechanical and weather problems. But glad they put safety first"

Pros: "They put safety first"
Cons: "Frustrating 4 hour delay"

Cons: "I am very disappointed in my flight. I am 6'7 and paid for an exit row seat. When I got to the airport they gave me a different seat with no leg room. They told me they changed planes and there was nothing they could do to help me. I tried again at the gate and again nothing. Will never fly again."

Pros: "Room on flight in coach was sufficient and im 6 ft 2"

Pros: "The entertainment was pretty good . There was a good variety of movies and music"
Cons: "the cabin was extremely small, absolutely no leg dpace unless you were in first class, specially if you are a taller person."

Pros: "Overall pleasant experience."
Cons: "I was not aware that the FinnAir flight was being handled by American. I missed it when reading my itinerary and had a brief panic when I showed up to the international terminal and my flight was not even listed on the board. Perhaps it could be written a little larger? Thanks."

Pros: "Good value"
Cons: "Poor food quality"

Cons: "That small space!! This is a long flight and you have no room to move around at all!!!!!"

Pros: "Appreciated that the cre didn't wake me to give me my landing card. They did make sure I got one though."

Cons: "I didn't get vegetarian food that I ordered over the phone and I did made sure that it said vegetarian Jain meal on the ticket that I printed. Very disappointed because no point ordering then. I paid $1234 for the trip. And I am traveling because of funeral."

Cons: "Seats too tight. No room"

Pros: "Food, entertainment and free checked bag. Can ask for more!"

Pros: "In flight service."
Cons: "The first check in kiosk associate was turning us away because we reached 30 minutes prior to scheduled departure. However, by then they knew that they were going to be at least 1 hour 30 minute late. Then when kayak emailed us about the delay, the check in people let us in. Ultimately the flight was three hours late."

Pros: "Food, blanket & pillow,"
Cons: "Most of the video screens did not work. Long flight with no entertainment!"

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."

Pros: "The flight was on time."

Pros: "Flight was on time."

Pros: "Flight itself was fine. Major delay resulted in arriving one day later than planned, additional transportation cost, unplanned, and unplanned parking fees. No travel voucher was offered and when I asked was told it was not possible to issue a travel voucher."

Pros: "The flight was good..."
Cons: "No entertainment was available ... even do they announced ..."

Pros: "In flight entertainment. Was able to watch a movie for free."

Pros: "Flight on time and arrived early"

Pros: "That I finally got there a day later. I only had carry on bags, so they weren't lost."
Cons: "At OHare the gate agent sent me to the wrong gate and plane for my flight. I did not arrive Thursday at 8:30 pm as scheduled. Customer service put me on "red eye" to Dulles for the next flight to Charleston, without motel or meal vouchers. I couldnt sleep on the benches there due to asthma and diabetic issues. I arrived Friday 2:30 pm 17 hours late. Dulles overnight cleaning staff helped more than agents at OHare."

Pros: "Good crew"
Cons: "Shitty seats was very uncomfortable probably won't fly United just because of that... Delta has a lot more comfortable seats"

Pros: "Seats were nice and crew was friendly"
Cons: "It wasn't their fault but we did have to land at a different airport due to weather, but it showed that the crew took safety first"

Pros: "Excellent service and friendly staff"
Cons: "Absolutely not enough room to stretch your legs"

Cons: "Some inspector idiot decided that the exterior cover stickers weren't "up to code" literally half an hour before my flight, delaying us 2 hours. I got onto a different flight at the last second, then the same thing happened to that plane. Brilliant on their parts. I almost lost a job interview thanks to your people."

Pros: "same as above"
Cons: "same as above"

Pros: "Getting to Charlotte"
Cons: "Plane dirty. Windows dirty. Extremely bumpy. Seats clostraphobic. Sat too long leaving"

Pros: "The flight crew apologized and kept everyone informed."
Cons: "The plane was having mechanical problems. Once it was determined that the problem couldn't be fixed it took the airline quite some time to locate a new plane. They should have started working to identify a new plane sooner. Ended up arriving in Portland after 3 am."

Pros: "Overall fine"

Pros: "flight was excellent"
Cons: "Monitor kept running commercials and a show i couldn't hear very annoying"

Pros: "The seats were perfect, a lot of leg room. Comfortable side pillows on the seats"
Cons: "All the rest including the absence of food"

Cons: "Why should I have to pay to watch tv? I know you don't have to pay on Southwest, Virgin America or Jet Blue. Not sure that a very (and I mean VERY SMALL) snack can be considered food"

Pros: "On time, gates were close together"

Pros: "Comfy environment, not completely booked plane"
Cons: "The price for one little bottle of Rum, highway robbery I say."

Cons: "The plane was delayed."

Pros: "Newer plane. Very nice staff"
Cons: "Floor around seat was dirty. Lot of exaggerated braking. Suggested a new pilot perhaps?"

Pros: "Getting from point a to point b."
Cons: "Lack of good free snacks. Not getting free bag checked."

Cons: "Deverted to Newark to get to portland"

Pros: "Duration of flight was shorter than expected. Arrived at destination fifteen minutes early."
Cons: "No complaints."

Pros: "Good"

Cons: "Delayed because there was no crew to fly the plane switched gates 6 different time other than that everything was good"

Pros: "I was incredibly disappointed that my luggage got sent on an earlier flight to Memphis from Chicago. When I arrived in Memphis after 24 hours of flying, I found my luggage locked up and no representative to be found. Exhausted, frustrated, and seeing my luggage through the glass door and not being able to retreave it, I was incredibly frustrated with United. If you are going to send luggage on a different flight, be there and available to let travelers claim their luggage. My entire flight had gotten their bags from baggage claim before I even found someone available to open the door. I had to get an American Airlines representative to call them to the area twice before they arrived. If you are going to do this, offer the traveler to be on the earlier flight too. I was very disappointed, especially after my flight was delayed by 45 minutes on top of it."
Cons: "The poor customer service."

Cons: "Never made it so I can't rate it"

Pros: "Everything went smoothly"

Pros: "Crew was nice"
Cons: "Flight was delayed. Food was terrible"

Pros: "Large plane very comfortable"
Cons: "Nothing"

Pros: "Nice service, friendly crew."

Pros: "Kind staff and crew."
Cons: "As usual, there were extensive delays. This time it was due to a plane change initially because there was a maintenance issue. Then, we had to walk across the airport to board our other plane at a gate on the other side. Then we had to wait for the crew to arrive before we could board. It wasn't until we finally were able to board that they discovered a maintenance issue on the second plane, so we sat on the tarmac in stifling heat due to the engine not being on for an hour and a half while they worked on the plane. We didn't take off until about 11:40 central time and arrive home until 1:30 AM eastern time instead of the scheduled 11:38 PM arrival time."

Pros: "Staff was great"
Cons: "Second delay in a row"

Pros: "Pilot/Crew Communication was frequent and accurate"
Cons: "Flight was delayed 1.5 hrs due to an electronic problem after we left the gate."

Cons: "Delays both ways"

Pros: "On Time, polite smiling crew, happy passengers, overall excellent."

Pros: "Totally on time: excellent everything. This was a smooth flight both ways."

Pros: "Flight wasn't full"
Cons: "Flight was delayed an hour due to maintenance repairs."

Cons: "There should be some free tv"

Pros: "Everything!"

Cons: "Many hours of delays from and to.."

Cons: "Had an extended overlay because of an overlap booking with our pilot. He was on another plane that wasn't due to come in until two hours later."

Pros: "Smoothly and on time"

Pros: "Willingness to check carry ons for sold out flights"
Cons: "Choosing of seats process. My traveling partner and I did not get to sit together on way home. Everyone was nice and got a free upgrade but would have been nice to sit together"

Pros: "My mother is disabled and was assigned wheelchair assistance and does not speak English very very hopeful does not have a cell phone because she is disable and does not know how to use a cell phone I was calling the one 800 number for united airlines they gave me a phone number for the terminal where she was delayed and I was just trying to check to see if my mother was aware of what was going on with the delay I just need to know if my mother was OK to give her comfort but unfortunately the number they gave me was not working I was calling over 30 rings with nobody answering for over three hours O'Hare airport was very hopeless for united airlines it's a shame that that is their head quarters i'm pretty sure I will never ever use United Airline again in my life after the terrifying experience I had waiting over four hours from my mother besides the four hour flight I was very terrified until my mother was in my arms I never ever want to experience that again or I hopefully nobody ever that uses your United airline will ever experience that"
Cons: "My mother is disabled and was assigned wheelchair assistance and does not speak English very very hopeful does not have a cell phone because she is disable and does not know how to use a cell phone I was calling the one 800 number for united airlines they gave me a phone number for the terminal where she was delayed and I was just trying to check to see if my mother was aware of what was going on with the delay I just need to know if my mother was OK to give her comfort but unfortunately the number they gave me was not working I was calling over 30 rings with nobody answering for over three hours O'Hare airport was very hopeless for united airlines it's a shame that that is their head quarters i'm pretty sure I will never ever use United Airline again in my life after the terrifying experience I had waiting over four hours from my mother besides the four hour flight I was very terrified until my mother was in my arms I never ever want to experience that again or I hopefully nobody ever that uses your United airline will ever experience that"

Pros: "Good customer service"

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 O'Hare Intl to Caribbean

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

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago O'Hare Intl to Caribbean

Mandatory masks

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

Social distancing seating

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

Pre-flight testing

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

Book cheap flights from Chicago O'Hare Airport to Caribbean

Recent round-trip flight deals

2/4
Thu
1 stop
Spirit Airlines
17h 27m
ORD - SJU
2/5
Fri
1 stop
Spirit Airlines
12h 03m
SJU - ORD
2/16
Tue
1 stop
Spirit Airlines
7h 05m
ORD - SJU
3/2
Tue
1 stop
Spirit Airlines
7h 48m
SJU - ORD
1/31
Sun
1 stop
Spirit Airlines
11h 40m
ORD - SJU
2/5
Fri
1 stop
Spirit Airlines
12h 03m
SJU - ORD
2/15
Mon
1 stop
Spirit Airlines
11h 40m
ORD - SJU
2/23
Tue
1 stop
Spirit Airlines
7h 48m
SJU - ORD
1/30
Sat
1 stop
Spirit Airlines
14h 57m
ORD - SJU
2/1
Mon
1 stop
Spirit Airlines
10h 33m
SJU - ORD
2/1
Mon
1 stop
Spirit Airlines
11h 40m
ORD - SJU
2/5
Fri
1 stop
Spirit Airlines
12h 03m
SJU - ORD
2/3
Wed
1 stop
Spirit Airlines
6h 40m
ORD - SJU
2/23
Tue
1 stop
Spirit Airlines
7h 48m
SJU - ORD
2/5
Fri
1 stop
Spirit Airlines
11h 40m
ORD - SJU
2/12
Fri
1 stop
Spirit Airlines
7h 48m
SJU - ORD
2/1
Mon
1 stop
Spirit Airlines
17h 27m
ORD - SJU
2/2
Tue
1 stop
Spirit Airlines
10h 33m
SJU - ORD
2/2
Tue
1 stop
Multiple Airlines
17h 27m
ORD - SJU
3/9
Tue
nonstop
Multiple Airlines
5h 35m
SJU - ORD
2/16
Tue
1 stop
Multiple Airlines
7h 05m
ORD - SJU
2/22
Mon
2 stops
Multiple Airlines
18h 31m
SJU - ORD
2/16
Tue
1 stop
Multiple Airlines
7h 05m
ORD - SJU
3/1
Mon
1 stop
Multiple Airlines
22h 04m
SJU - ORD
3/1
Mon
1 stop
Multiple Airlines
11h 40m
ORD - SJU
3/3
Wed
1 stop
Multiple Airlines
22h 04m
SJU - ORD
2/16
Tue
1 stop
Multiple Airlines
7h 05m
ORD - SJU
2/23
Tue
2 stops
Multiple Airlines
18h 31m
SJU - ORD
1/26
Tue
1 stop
Multiple Airlines
17h 27m
ORD - SJU
1/31
Sun
1 stop
Multiple Airlines
10h 54m
SJU - ORD
2/14
Sun
nonstop
United Airlines
4h 30m
ORD - PUJ
2/17
Wed
nonstop
United Airlines
5h 05m
PUJ - ORD
2/14
Sun
1 stop
United Airlines
16h 10m
ORD - PUJ
2/21
Sun
nonstop
United Airlines
5h 05m
PUJ - ORD
4/23
Fri
1 stop
American Airlines
17h 42m
ORD - STX
4/28
Wed
1 stop
American Airlines
7h 11m
STX - ORD
4/21
Wed
1 stop
American Airlines
6h 52m
ORD - STX
4/28
Wed
1 stop
American Airlines
7h 11m
STX - ORD
2/20
Sat
1 stop
JetBlue
6h 34m
ORD - SDQ
2/27
Sat
1 stop
JetBlue
8h 24m
SDQ - ORD
Show more results

Recent one-way flight deals

3/9
Tue
1 stop
Spirit Airlines
11h 30m
ORD - SJU
2/2
Tue
1 stop
Spirit Airlines
17h 27m
ORD - SJU
2/8
Mon
1 stop
Spirit Airlines
11h 40m
ORD - SJU
2/8
Mon
1 stop
Spirit Airlines
17h 27m
ORD - SJU
2/3
Wed
1 stop
Spirit Airlines
6h 40m
ORD - SJU
2/8
Mon
1 stop
Spirit Airlines
11h 40m
ORD - SJU
2/15
Mon
2 stops
Spirit Airlines
23h 05m
ORD - SJU
2/13
Sat
2 stops
Multiple Airlines
19h 04m
ORD - SJU
1/28
Thu
1 stop
Frontier
12h 51m
ORD - SJU
2/20
Sat
2 stops
Multiple Airlines
19h 04m
ORD - SJU
2/10
Wed
1 stop
Multiple Airlines
25h 40m
ORD - SJU
3/8
Mon
nonstop
Frontier
4h 43m
ORD - SJU
4/19
Mon
nonstop
Frontier
4h 55m
ORD - SJU
2/10
Wed
2 stops
Multiple Airlines
38h 30m
ORD - SJU
2/3
Wed
nonstop
United Airlines
4h 30m
ORD - PUJ
2/11
Thu
1 stop
United Airlines
7h 55m
ORD - PUJ
3/6
Sat
1 stop
JetBlue
9h 42m
ORD - NAS
2/16
Tue
1 stop
American Airlines
8h 02m
ORD - PUJ
3/25
Thu
1 stop
Copa Airlines
27h 49m
ORD - PUJ
2/11
Thu
1 stop
Delta
5h 01m
ORD - NAS
Show more results
-
1
  • Round-trip
  • One-way
  • Multi-city
  • Trip Builder
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First