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Find cheap flights from Chicago O'Hare Airport to Caribbean Islands from $88

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 Islands departing on 6/25. 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
mer. 6/26
mer. 7/3

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Best Caribbean Islands Flight Deals

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

Punta Cana
Punta Cananonstop$213
Montego Bay
Montego Bay1 stop$272
Santo Domingo
Santo Domingo2 stops$281
Oranjestad
Oranjestad1 stop$283
Nassau
Nassau2 stops$422
Kingston
Kingston1 stop$366
Simpson Bay
Simpson Bay1 stop$275
Providenciales
Providenciales1 stop$459
Port of Spain
Port of Spain2 stops$366
Bridgetown
Bridgetown2 stops$427
George Town
George Town1 stop$415
Aguadilla
Aguadilla1 stop$296
Willemstad
Willemstad3 stops$493
Castries
Castries2 stops$775
St. John's
St. John's1 stop$609

Good to know

Low season

September

High season

December

Cheapest flight

$88
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Chicago O'Hare Airport to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

  • 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 Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 5 airlines serving from O'Hare Intl to Caribbean Islands

 
Need help choosing which airline to fly with from O'Hare Intl to Caribbean Islands? 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 10512 reviews
7.4Food
7.9Comfort
8.6Crew
8.0Entertainment
8.2Boarding
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

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

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.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

Flight was cancelled just 6 days before. No more flights that day, and the following date was sold out. Had to obtain a refund and buy more expensive flights on another airline.

The flight was on time and nice as always for me with spirit but the cabin crew were not good. They left the lights on on a red eye for the entire flight.

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

This recognisable no-frills airline gets me from point-A to point-B. I was able to get to Chicago without stress. The checked baggage collection and reclaim could be improved.

The crew was the best and very accommodating I know you don't offer any complimentary items but water and coffee will not break the bank !!

My flight was cancelled!!! I had to spend 200.00 on another flight!!

The whole day was a nightmare. Flight extremely late. Boarding was a mess of a nightmare.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Book cheap flights from Chicago to Caribbean Islands

Recent round-trip flight deals

9/10mar.
1 stopSpirit Airlines
10h 32mORD-STT
9/17mar.
1 stopSpirit Airlines
7h 35mSTT-ORD
$173
8/22jeu.
nonstopSpirit Airlines
4h 48mORD-SJU
8/24sam.
1 stopSpirit Airlines
9h 04mSJU-ORD
$193
8/6mar.
nonstopFrontier
4h 44mORD-PUJ
8/10sam.
nonstopFrontier
5h 11mPUJ-ORD
$213
8/2ven.
1 stopFrontier
28h 07mORD-PUJ
8/8jeu.
1 stopFrontier
10h 43mPUJ-ORD
$251
8/18dim.
1 stopAmerican Airlines
9h 22mORD-PUJ
8/22jeu.
nonstopAmerican Airlines
5h 00mPUJ-ORD
$304
9/23lun.
1 stopAmerican Airlines
17h 12mORD-PUJ
9/27ven.
1 stopAmerican Airlines
17h 33mPUJ-ORD
$315
10/19sam.
1 stopUnited Airlines
14h 05mORD-PUJ
10/24jeu.
1 stopUnited Airlines
7h 39mPUJ-ORD
$395
10/26sam.
1 stopUnited Airlines
17h 48mORD-PUJ
11/2sam.
1 stopUnited Airlines
7h 47mPUJ-ORD
$405
7/19ven.
1 stopDelta
6h 26mORD-NAS
7/23mar.
2 stopsDelta
18h 10mNAS-ORD
$453
11/11lun.
1 stopDelta
5h 44mORD-PLS
11/15ven.
1 stopDelta
8h 04mPLS-ORD
$462

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Recent one-way flight deals

6/25mar.
1 stopSpirit Airlines
15h 12mORD-SJU
$88
8/11dim.
nonstopFrontier
4h 44mORD-PUJ
$89
8/13mar.
nonstopAmerican Airlines
4h 35mORD-PUJ
$132
5/29mer.
1 stopAmerican Airlines
10h 40mORD-SJU
$136
7/24mer.
nonstopUnited Airlines
4h 36mORD-PUJ
$195
6/1sam.
nonstopUnited Airlines
4h 47mORD-SJU
$208
8/4dim.
2 stopsDelta
8h 38mORD-NAS
$228
6/4mar.
2 stopsAir Canada
18h 50mORD-NAS
$238
6/4mar.
1 stopAir Canada
20h 15mORD-NAS
$239
8/4dim.
2 stopsDelta
8h 38mORD-NAS
$273

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Last minute flights from O'Hare Intl to Caribbean Islands

Last minute flight, train and bus deals

5/31ven.
nonstopSpirit Airlines
4h 53mORD-SJU
6/3lun.
multi-stopSpirit Airlines
13h 48mSJU-ORD
$205
5/30jeu.
nonstopSpirit Airlines
4h 53mORD-SJU
6/4mar.
multi-stopSpirit Airlines
20h 49mSJU-ORD
$216
5/28mar.
multi-stopAmerican Airlines
9h 35mORD-SJU
5/31ven.
multi-stopAmerican Airlines
8h 18mSJU-ORD
$265
5/29mer.
multi-stopAmerican Airlines
7h 14mORD-SJU
6/3lun.
multi-stopAmerican Airlines
8h 18mSJU-ORD
$266
5/31ven.
multi-stopFrontier
13h 50mORD-PUJ
6/7ven.
multi-stopFrontier
9h 16mPUJ-ORD
$276
6/1sam.
multi-stopFrontier
20h 08mORD-SXM
6/8sam.
multi-stopFrontier
27h 45mSXM-ORD
$293
5/28mar.
nonstopUnited Airlines
4h 50mORD-SJU
6/3lun.
multi-stopUnited Airlines
10h 30mSJU-ORD
$386
5/29mer.
nonstopUnited Airlines
4h 36mORD-PUJ
6/5mer.
nonstopUnited Airlines
4h 59mPUJ-ORD
$481
5/29mer.
multi-stopDelta
12h 10mORD-SDQ
6/12mer.
multi-stopDelta
15h 58mSDQ-ORD
$483
5/30jeu.
multi-stopDelta
16h 36mORD-SDQ
6/3lun.
multi-stopDelta
18h 10mSDQ-ORD
$535

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Chicago O'Hare Airport - Caribbean Islands Flights

Departure:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Caribbean Islands - Chicago O'Hare Airport

Cabin classes:

$172
$194
$296
$38

Browse destinations:

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