$113 Find Cheap Flights from Caribbean Islands to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 5/6. 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
1 adult, Economy, 0 bags

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Cheap Flights from Caribbean Islands to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean Islands to Chicago

Fri, May 1 - Mon, May 4
Spirit Airlines Logo
12:57 pm - 12:24 am
SJU
-
ORD
12h 27m
1 stop
Spirit Airlines Logo
4:44 pm - 10:21 pm
ORD
-
SJU
4h 37mnonstop
$147Spirit Airlines
Thu, Apr 30 - Mon, May 4
Spirit Airlines Logo
4:34 pm - 8:49 pm
SJU
-
ORD
5h 15mnonstop
Spirit Airlines Logo
4:44 pm - 10:21 pm
ORD
-
SJU
4h 37mnonstop
$150Spirit Airlines
Fri, May 15 - Sat, May 30
Frontier Logo
11:00 am - 11:59 pm
SJU
-
ORD
13h 59m
1 stop
Frontier Logo
12:33 am - 6:24 am
ORD
-
SJU
4h 51mnonstop
$152Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
6:09 pm - 11:13 pm
SJU
-
ORD
30h 04m
1 stop
Frontier Logo
7:30 am - 11:28 pm
ORD
-
SJU
14h 58m
1 stop
$159Frontier
Thu, Jul 16 - Sun, Jul 19
American Airlines Logo
2:23 pm - 7:16 pm
MBJ
-
ORD
4h 53mnonstop
American Airlines Logo
9:13 am - 1:23 pm
ORD
-
MBJ
4h 10mnonstop
$281American Airlines
Sat, May 16 - Mon, May 18
United Airlines Logo
1:52 pm - 6:15 pm
MBJ
-
ORD
4h 23mnonstop
United Airlines Logo
11:00 pm - 1:30 pm
ORD
-
MBJ
14h 30m
1 stop
$286United Airlines
Fri, Aug 21 - Wed, Aug 26
American Airlines Logo
2:00 pm - 6:30 pm
MBJ
-
ORD
4h 30mnonstop
American Airlines Logo
7:30 am - 1:28 pm
ORD
-
MBJ
5h 58m
1 stop
$291American Airlines
Fri, May 8 - Tue, May 12
United Airlines Logo
4:12 pm - 4:30 pm
MBJ
-
ORD
24h 18m
1 stop
United Airlines Logo
10:30 am - 1:30 pm
ORD
-
MBJ
27h 00m
1 stop
$292United Airlines
Fri, May 1 - Wed, May 6
Delta Logo
6:00 am - 9:57 pm
STI
-
ORD
16h 57m
1 stop
Delta Logo
8:15 am - 12:22 am
ORD
-
STI
15h 07m
2 stops
$471Delta
Wed, May 6 - Sat, May 9
Delta Logo
6:00 am - 5:41 pm
STI
-
ORD
12h 41m
1 stop
Delta Logo
6:07 am - 7:29 pm
ORD
-
STI
12h 22m
1 stop
$495Delta
Useful Info

Good to know

Low seasonMarch
Cheapest flight$113
Best time to beat the crowds but there is an average 39% increase in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from San Juan to Chicago Midway Airport

FAQs for booking flights from Caribbean Islands to Chicago

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

    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 Caribbean Islands to Chicago.

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

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

    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 Chicago with an airline and back to Caribbean Islands with another airline.

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

    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 Chicago from Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Caribbean Islands to Chicago

 
Need help choosing which airline to fly with from Caribbean Islands to Chicago? 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.
7.9
DeltaOverall score based on 8404 reviews
7.9Comfort
8.5Crew
8.1Boarding
7.2Food
7.8Entertainment
Airline reviews

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

10.0 ExcellentTeresa, Apr 2026
SMF - LAX
Read more Delta reviews

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

The crew was generally professional. Though one of the crew members seemed to be easily annoyed, the others were fine and helpful. The green olives and almonds snack was really good. A great idea, and nice balance of tastes.

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

Food and drink service was very low quality. The flight attendants in business class must have been short some staff. Service was sluggish and not much English was spoken

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
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Lansing
Valparaiso
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Saint John

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Caribbean Islands

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