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Find cheap flights from Chicago to Caribbean Islands from $69

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Caribbean Islands departing on 5/9. 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
Sun 5/26
Sun 6/2

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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 Cana1 stop$209
Montego Bay
Montego Bay1 stop$345
Santo Domingo
Santo Domingo1 stop$242
Oranjestad
Oranjestad1 stop$281
Nassau
Nassau1 stop$350
Kingston
Kingston1 stop$328
Simpson Bay
Simpson Bay1 stop$179
Providenciales
Providenciales1 stop$459
George Town
George Town1 stop$405
Aguadilla
Aguadilla1 stop$198
St. John's
St. John's1 stop$604

Good to know

Low season

September

High season

March

Cheapest flight

$69
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago Midway Airport to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Chicago 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 to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago 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 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 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 with another airline.

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

 
Need help choosing which airline to fly with from Chicago 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 10966 reviews
8.2boarding
7.9comfort
8.6crew
8.0entertainment
7.4food
Airline reviews

Delta is one of the best airlines I have flown

10.0 ExcellentKellie, Apr 2024ANC - SEA
Read more about Delta reviews

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

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.

my seat got changed twice after checking on then boarding it had been given to a family so by the time they found a seat for me no overhead storage left. i ended up losing my Sony Headphones case because i could even access underthe seat in front of my when deplaning.

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.

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.

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. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

I do not like the customer service, I had an emergency and needed to cancel a pet reservation right after I had booked it and they would not do anything but issue a credit. I haven't flown in years as I have 7 kids and don't have spare time. I want my $125 back on my card please

Spirit airline tries to screw you at every opportunity. Spirit wanted 65$ for an extra pound in the suitcase Made me open the suitcase at the counter to remove 1 pound. Staff very cold and rude Will never fly spirit again and will recommend same to family and friends

Delayed..4 times...completely disorganized boarding. After 5 hours they scrambled to move ppl off plane bc they overbooked. Then they didn't have a cabin crew. WiFi on plane didn't work. Zero amenities. Once we boarded we sat on tarmac for an hour. Explore all alternate options including purchasing a pair of hiking boots and walking to your destination instead of flying spirit.

what I like about Spirit is that the pilot and crew are good communicators. The plane itself - well, its a budget airline and you get what is expected, But I generally just feel safer, somehow, when I know more about what is going on - and Spirit has always done a good job of telling me what is going on: why the delay, why the turbulence, why this and that... and that means a lot to me.

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.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

Book cheap flights from Chicago to Caribbean Islands

Recent round-trip flight deals

5/21Tue
1 stopFrontier
11h 49mMDW-SJU
5/22Wed
1 stopFrontier
16h 05mSJU-MDW
$135
5/14Tue
1 stopFrontier
11h 39mMDW-SJU
5/18Sat
1 stopFrontier
29h 24mSJU-MDW
$136
5/15Wed
1 stopSpirit Airlines
13h 54mORD-STT
5/22Wed
1 stopSpirit Airlines
8h 14mSTT-ORD
$175
5/8Wed
1 stopSpirit Airlines
19h 00mORD-SJU
5/13Mon
1 stopSpirit Airlines
20h 40mSJU-ORD
$186
5/6Mon
1 stopAmerican Airlines
7h 10mORD-PUJ
5/12Sun
1 stopAmerican Airlines
15h 52mPUJ-ORD
$349
5/3Fri
1 stopAmerican Airlines
17h 12mORD-PUJ
5/6Mon
1 stopAmerican Airlines
19h 04mPUJ-ORD
$365
8/12Mon
1 stopDelta
5h 07mORD-NAS
8/15Thu
1 stopDelta
7h 44mNAS-ORD
$423
7/8Mon
2 stopsDelta
15h 38mORD-NAS
7/12Fri
2 stopsDelta
16h 46mNAS-ORD
$428
6/30Sun
nonstopUnited Airlines
3h 23mORD-NAS
7/7Sun
nonstopUnited Airlines
3h 45mNAS-ORD
$433
6/25Tue
1 stopUnited Airlines
17h 22mORD-NAS
7/6Sat
nonstopUnited Airlines
3h 45mNAS-ORD
$438

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Recent one-way flight deals

5/9Thu
1 stopFrontier
7h 19mMDW-SJU
$69
5/13Mon
1 stopFrontier
12h 17mMDW-SJU
$71
4/30Tue
nonstopSpirit Airlines
4h 43mORD-SJU
$87
4/29Mon
nonstopSpirit Airlines
4h 43mORD-SJU
$88
5/15Wed
nonstopAmerican Airlines
4h 40mORD-SJU
$139
7/20Sat
2 stopsAmerican Airlines
18h 55mORD-SJU
$142
5/28Tue
nonstopUnited Airlines
4h 36mORD-PUJ
$152
9/26Thu
1 stopDelta
15h 41mORD-MBJ
$211
6/30Sun
nonstopUnited Airlines
3h 23mORD-NAS
$224
7/28Sun
2 stopsDelta
16h 49mORD-NAS
$234

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Last minute flights from Chicago to Caribbean Islands

Last minute flight, train and bus deals

4/30Tue
nonstopSpirit Airlines
4h 43mORD-SJU
5/14Tue
multi-stopSpirit Airlines
13h 48mSJU-ORD
$134
4/30Tue
nonstopSpirit Airlines
4h 43mORD-SJU
5/14Tue
multi-stopSpirit Airlines
34h 35mSJU-ORD
$153
5/1Wed
multi-stopFrontier
9h 38mMDW-SJU
5/11Sat
multi-stopFrontier
8h 50mSJU-MDW
$196
5/1Wed
multi-stopFrontier
12h 31mMDW-SJU
5/10Fri
multi-stopFrontier
17h 18mSJU-MDW
$197
4/30Tue
nonstopAmerican Airlines
4h 40mORD-SJU
5/6Mon
multi-stopAmerican Airlines
8h 50mSJU-ORD
$241
4/29Mon
multi-stopAmerican Airlines
17h 10mORD-SJU
5/2Thu
multi-stopAmerican Airlines
17h 20mSJU-ORD
$242
4/27Sat
nonstopUnited Airlines
4h 47mORD-SJU
5/15Wed
multi-stopUnited Airlines
10h 17mSJU-ORD
$257
4/27Sat
nonstopUnited Airlines
4h 47mORD-SJU
5/15Wed
nonstopUnited Airlines
5h 11mSJU-ORD
$325
4/30Tue
multi-stopDelta
7h 40mMDW-PUJ
5/1Wed
multi-stopDelta
8h 13mPUJ-MDW
$435
4/27Sat
multi-stopDelta
17h 13mORD-PUJ
5/1Wed
multi-stopDelta
16h 35mPUJ-ORD
$440

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