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Find cheap flights from Chicago O'Hare Airport to Caribbean from $57

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Caribbean departing on 5/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Tue 6/4
Tue 6/11

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Best Caribbean Flight Deals

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

Punta Cana
Punta Cana1 stop$223
Montego Bay
Montego Bay1 stop$362
Santo Domingo
Santo Domingo1 stop$274
Oranjestad
Oranjestad1 stop$277
Nassau
Nassau1 stop$359
Kingston
Kingston1 stop$334
Simpson Bay
Simpson Bay1 stop$184
Providenciales
Providenciales1 stop$457
Port of Spain
Port of Spain1 stop$440
Bridgetown
Bridgetown2 stops$341
George Town
George Town1 stop$444
Aguadilla
Aguadilla1 stop$244
Castries
Castries2 stops$915
Willemstad
Willemstad2 stops$445
St. John's
St. John's1 stop$609

Good to know

Low season

September

High season

December

Cheapest flight

$57
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 21% increase in price.
Flight from Chicago O'Hare Airport to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago O'Hare Airport 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?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean from Chicago O'Hare Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago O'Hare Airport to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Caribbean with an airline and back to Chicago O'Hare Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Caribbean from Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Morning departure is around 4% 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

Top 5 airlines serving from O'Hare Intl to Caribbean

 
Need help choosing which airline to fly with from O'Hare Intl to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10826 reviews
8.6Crew
7.9Comfort
8.0Entertainment
8.2Boarding
7.4Food
Airline reviews

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

10.0 ExcellentBranton, May 2024AVL - ATL
Read more about Delta reviews

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

Book cheap flights from Chicago to Caribbean

Recent round-trip flight deals

5/21Tue
1 stopSpirit Airlines
13h 11mORD-SJU
5/25Sat
1 stopSpirit Airlines
9h 00mSJU-ORD
$120
6/4Tue
1 stopSpirit Airlines
17h 00mORD-SJU
6/8Sat
1 stopSpirit Airlines
8h 21mSJU-ORD
$132
5/18Sat
1 stopFrontier
20h 11mORD-SXM
5/25Sat
1 stopFrontier
9h 44mSXM-ORD
$184
5/18Sat
1 stopFrontier
7h 13mORD-SJU
5/20Mon
1 stopFrontier
27h 45mSJU-ORD
$198
5/12Sun
nonstopAmerican Airlines
4h 35mORD-PUJ
5/16Thu
nonstopAmerican Airlines
5h 05mPUJ-ORD
$237
5/12Sun
1 stopAmerican Airlines
9h 05mORD-PUJ
5/16Thu
nonstopAmerican Airlines
5h 05mPUJ-ORD
$282
7/9Tue
1 stopDelta
5h 07mORD-NAS
7/16Tue
2 stopsDelta
14h 57mNAS-ORD
$428
5/29Wed
2 stopsDelta
17h 48mORD-SDQ
6/12Wed
2 stopsDelta
16h 38mSDQ-ORD
$433
5/18Sat
nonstopUnited Airlines
4h 00mORD-MBJ
5/25Sat
nonstopUnited Airlines
4h 24mMBJ-ORD
$435
8/2Fri
nonstopUnited Airlines
4h 00mORD-MBJ
8/6Tue
1 stopUnited Airlines
15h 28mMBJ-ORD
$444

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Recent one-way flight deals

5/14Tue
1 stopSpirit Airlines
20h 42mORD-SJU
$57
5/29Wed
nonstopSpirit Airlines
4h 53mORD-SJU
$62
5/18Sat
1 stopFrontier
15h 51mORD-SJU
$63
5/21Tue
1 stopFrontier
11h 28mORD-SJU
$69
7/12Fri
2 stopsAmerican Airlines
24h 14mORD-SJU
$142
8/25Sun
1 stopAmerican Airlines
8h 49mORD-SJU
$143
7/3Wed
nonstopUnited Airlines
4h 36mORD-PUJ
$187
5/15Wed
nonstopUnited Airlines
4h 50mORD-SJU
$189
7/14Sun
1 stopDelta
7h 38mORD-PUJ
$211
7/15Mon
2 stopsDelta
18h 09mORD-PUJ
$212

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Last minute flights from O'Hare Intl to Caribbean

Last minute flight, train and bus deals

5/7Tue
multi-stopSpirit Airlines
13h 41mORD-SJU
5/11Sat
nonstopSpirit Airlines
5h 10mSJU-ORD
$189
5/8Wed
nonstopSpirit Airlines
4h 53mORD-SJU
5/14Tue
multi-stopSpirit Airlines
22h 16mSJU-ORD
$196
5/7Tue
multi-stopFrontier
27h 24mORD-PUJ
5/8Wed
nonstopFrontier
5h 29mPUJ-ORD
$248
5/7Tue
multi-stopAmerican Airlines
6h 30mORD-SJU
5/20Mon
multi-stopAmerican Airlines
8h 50mSJU-ORD
$252
5/7Tue
multi-stopAmerican Airlines
6h 10mORD-SJU
5/10Fri
nonstopAmerican Airlines
5h 15mSJU-ORD
$260
5/7Tue
nonstopUnited Airlines
4h 50mORD-SJU
5/7Tue
multi-stopUnited Airlines
7h 34mSJU-ORD
$266
5/7Tue
multi-stopFrontier
14h 18mORD-PUJ
5/8Wed
nonstopFrontier
5h 29mPUJ-ORD
$273
5/7Tue
multi-stopDelta
8h 04mORD-SJU
5/8Wed
multi-stopDelta
7h 20mSJU-ORD
$354
5/7Tue
nonstopUnited Airlines
4h 50mORD-SJU
5/7Tue
multi-stopUnited Airlines
8h 34mSJU-ORD
$356
5/7Tue
multi-stopDelta
6h 45mORD-PUJ
5/8Wed
multi-stopDelta
10h 05mPUJ-ORD
$435

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Chicago O'Hare Airport - Caribbean Flights

Departure:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Caribbean - Chicago O'Hare Airport

Cabin classes:

$872
$435
$1,002
$178