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$56 Find Cheap Flights from Illinois to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Illinois to Caribbean departing on 10/30. 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

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Low season

September

High season

December

Cheapest flight

$56
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 for booking flights from Illinois to Caribbean

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

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean from Illinois 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 Illinois 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 Illinois with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois 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 Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Illinois to Caribbean

Need help choosing which airline to fly with from Illinois 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.
8.9
Cape AirOverall score based on 46 reviews
8.9Entertainment
8.6Food
9.3Crew
8.6Boarding
8.3Comfort
Airline reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10.0 ExcellentSonia, Apr 2023CPX - SJU
Read more Cape Air reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10 seat Cesna. Equal parts transportation and adventure. 20 minute hop at 10000 feet and 160 mph, sitting 10 feet from the pilot. Panoramic views of the island. Very simple boarding, very low stress. VQS airport tiny, undeveloped. Highly recommended flight, Cape Air doing a great job here.

We traveled in a small Cesna so there was no food or entertainment. The pilot was excellent enjoy being able to see the places we were flying above. It was an OK flight.

Very smooth flight and landing. Pilot delivered his safety instruction in such a monotone that it wasn’t easily understandable. Words were said but he didn't communicate to us. If he was communicating to someone he cared about, he would have used inflection and other nuances of speaking. Virtually all emphasis was removed so it was just blah blah blah (really fast, like the end of a Pharma commercial)

My pilot on Cape Air was AMAZING!!!! I hoping that next time I fly I have him as my pilot. He made me feel safe and secure in his skills.

I so appreciate this service into and out of Glendive. Always a good experience with crew and support team.

It was not what I had expected but it was a great way to see the landscape.

Pros: "ground crew, pilot, flight was smooth and gate connections to Jet Blue in Boston were fantastic!"
Cons: "leg room"
Pros: "The pilot was kind and to the point."
Cons: "The guy who boarded us told me to wait as his computer could not check me in. 10min later he is rushing me to get on the runway. It was 30min before scheduled take off. I had ordered food and had to cancel my order before the café had finished, so he wasted food and did not get paid and I was hurried and boarded the plane hungry. I probably won't use Cape Air again unless it's an emergency situation"
Cons: "Boarded half hour late. No explanation. Pretty standard on Cape Air these days"

My flight from Avianca was 45 minutes late and it's very complicated to recheck in in ...also I have to say the silver desk folks were neither efficient nor helpful...so I missed my connecting flight. I actually got there before tge flight left but they refused to let me on....and gave me no vouchers for hotel etc

The cancelled our flight 3 times and we never made it to our destination. Every single airplane had a maintenance problem. Never fly this airline

9 hrs wait in airport then flt redirected to airport an hour away from our booked airport. Then at 8:00pm flight Cancelled. Silver supposed to book us on American the next day. Booked my husband but not me. Cost me Ubers, hotel, meals, new ticket and 1 hour taxi Cuz no flights to our home airport. Absolute disaster. Silver staff had no idea what was going on or what to do. Never Again Silver

Nothing about this flight was good. They are always cancelling or grossly delayed. We were delayed for 45 minutes for no apparent reason with no explanation or anything we could see and I missed my connection to Durham NC. I was on my way to my best friends memorial and funeral. Now I'll missed them both!!

Total disaster! The easiest flight was kept delayed till … cancelled! And before official announcement of the flight cancellation I was offered to join ongoing boarding to FLL so I had to change all my traveling plans, have lost my car reservation and a payed spot at the meeting I was going for to begin with! I had to no show to my flight back, because it was from different airport again!

The worst experience we had traveling. The worst experience we have had traveling. The service is lousy, I will NEVER choose this airline again.

Never in time always late, even on arrival gate not ready so waited on tarmac another 45 min

Flight canceled 11 hours after being delayed. Miss annual family vacation because of this

This was a short flight so food was not offered. The stewardess was great at giving water out. The baggage check at the airport was hideous. One person was untrained and had asked a question. The other two people were just dealing. Someone could have worked the line and said you must have a luggage tag and you must have confirmation. We waited for some people at the counter for 20 minutes because they couldn't find their reservation or they were missing their luggage tags. We were in line an hour and 20 minutes had to run to her gate just to find out our flight was delayed 40 minutes. The silver air website never updated with status changes on the phone. Horribly irresponsible flight company.

I like that the crew member offered to hand me my carry in after I walked up the stairs

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

Pros: "Nothing!!! Horrible airline with horrible staff members."
Cons: "Everything. The staff and crew of Intercaribbean airlines are very unprofessional and not helpful at all. On top of the flight delays all the luggage for that particular flight was left in Kingston. Everybody was rather nonchalant and unapologetic about the situation. I was told I would get the the following day. The next day only two of my three bags showed up. I was not compensated for the inconvenience and was told point blank that they will only deliver one of my bags to my address even though they were the reason I had NONE of my luggage in the first place. They are disgusting!!! I would never recommend this airline to anyone."
Pros: "Nice people"
Cons: "A long walk to the D3 gate, but there were no amenities there I.e. snacks (to be fair a new terminal is under construction)"
Cons: "There was no air. I understand when you are on the ground it can be limited but even after getting to altitude there was no air conditioning."
Cons: "The flight was delayed for over three hours, apparently it is a regular occurence."

Friendly staff, easy, and on time. Needs improvement on booking directly. Also

No comments, the complete handling and flying was excellent,keep up the good works.

Book cheap flights from Illinois to Caribbean

Recent round-trip flight deals

12/6Fri
1 stopFrontier
16h 47mMDW-SJU
12/9Mon
1 stopFrontier
13h 47mSJU-MDW
$158
10/28Mon
nonstop
4h 45mORD-SJU
11/2Sat
1 stop
12h 59mSJU-ORD
$159
11/15Fri
nonstopSpirit Airlines
4h 30mORD-SJU
11/20Wed
nonstopSpirit Airlines
5h 29mSJU-ORD
$179
10/26Sat
1 stopSpirit Airlines
15h 24mORD-SJU
11/2Sat
nonstopSpirit Airlines
5h 19mSJU-ORD
$181
10/23Wed
1 stopAmerican Airlines
14h 06mORD-SJU
11/1Fri
1 stopAmerican Airlines
11h 15mSJU-ORD
$220
10/30Wed
1 stopSouthwest
10h 15mMDW-SJU
11/6Wed
1 stopSouthwest
10h 05mSJU-MDW
$220
12/10Tue
1 stopAmerican Airlines
7h 02mORD-SJU
12/11Wed
1 stopAmerican Airlines
12h 59mSJU-ORD
$260
10/23Wed
1 stopSouthwest
7h 55mMDW-SJU
10/30Wed
1 stopSouthwest
9h 15mSJU-MDW
$265
11/16Sat
1 stopJetBlue
6h 59mORD-NAS
11/23Sat
1 stopJetBlue
11h 56mNAS-ORD
$399
11/20Wed
1 stopJetBlue
7h 22mORD-PUJ
11/24Sun
1 stopJetBlue
14h 02mPUJ-ORD
$424

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Recent one-way flight deals

10/30Wed
1 stopFrontier
11h 44mORD-SJU
$56
11/7Thu
1 stopFrontier
17h 19mORD-SJU
$57
10/25Fri
1 stopFrontier
28h 29mORD-SJU
$63
11/4Mon
1 stopSpirit Airlines
15h 36mORD-SJU
$80
10/28Mon
nonstopSpirit Airlines
4h 45mORD-SJU
$81
11/5Tue
2 stopsSouthwest
11h 05mORD-SJU
$110
11/6Wed
1 stopSouthwest
9h 20mMDW-SJU
$110
11/4Mon
1 stopJetBlue
6h 07mORD-NAS
$139
11/25Mon
1 stopJetBlue
10h 07mORD-MBJ
$177
10/16Wed
1 stopCopa Airlines
19h 09mORD-PUJ
$343

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Last minute flights from Illinois to Caribbean

Last minute flight, train and bus deals

10/12Sat
multi-stopSpirit Airlines
14h 23mORD-SJU
10/17Thu
multi-stopSpirit Airlines
24h 34mSJU-ORD
$302
10/12Sat
multi-stopFrontier
12h 36mORD-SJU
10/19Sat
multi-stopFrontier
11h 13mSJU-ORD
$318
10/9Wed
multi-stopSouthwest
10h 50mMDW-SJU
11/16Sat
multi-stopSouthwest
8h 35mSJU-MDW
$347
10/13Sun
multi-stop
9h 56mORD-SJU
10/18Fri
multi-stop
15h 27mSJU-ORD
$367
10/12Sat
multi-stop
12h 36mORD-SJU
10/19Sat
nonstop
5h 19mSJU-ORD
$370
10/12Sat
multi-stopAmerican Airlines
10h 20mORD-SJU
10/17Thu
multi-stopAmerican Airlines
13h 13mSJU-ORD
$394
10/10Thu
multi-stopAmerican Airlines
10h 35mORD-SJU
10/11Fri
multi-stopAmerican Airlines
16h 48mSJU-ORD
$419
10/10Thu
multi-stopSouthwest
13h 20mMDW-SJU
10/12Sat
multi-stopSouthwest
7h 20mSJU-MDW
$429
10/11Fri
multi-stopUnited Airlines
12h 00mORD-SJU
10/12Sat
nonstopUnited Airlines
5h 03mSJU-ORD
$466
10/9Wed
nonstopUnited Airlines
4h 47mORD-SJU
10/9Wed
multi-stopUnited Airlines
10h 29mSJU-ORD
$548

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Everything you need to know for your flight to Caribbean

Cabin class types available on flights to Illinois
Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.