$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 5/21. 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

Mon, Aug 10 - Mon, Aug 24
Frontier Logo
3:06 am - 11:05 pm
SJU
-
ORD
20h 59m
1 stop
Frontier Logo
12:29 am - 6:26 am
ORD
-
SJU
4h 57mnonstop
$201Frontier
Thu, Sep 3 - Mon, Sep 7
Frontier Logo
6:11 pm - 10:26 pm
SJU
-
ORD
5h 15mnonstop
Frontier Logo
12:29 am - 6:26 am
ORD
-
SJU
4h 57mnonstop
$220Frontier
Wed, Sep 2 - Tue, Sep 8
American Airlines Logo
12:59 am - 5:00 am
SJU
-
ORD
5h 01mnonstop
American Airlines Logo
5:00 am - 1:43 pm
ORD
-
SJU
7h 43m
1 stop
$222American Airlines
Tue, Aug 25 - Sun, Aug 30
American Airlines Logo
7:14 pm - 7:34 am
SJU
-
ORD
13h 20m
1 stop
American Airlines Logo
6:45 am - 2:53 pm
ORD
-
SJU
7h 08m
1 stop
$226American Airlines
Wed, Aug 19 - Sun, Sep 6
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
6:00 am - 4:35 pm
MDW
-
SJU
9h 35m
1 stop
$226Delta
Sat, Sep 5 - Tue, Sep 8
Southwest Logo
5:05 am - 1:10 pm
SJU
-
MDW
9h 05m
2 stops
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
2 stops
$236Southwest
Thu, Aug 27 - Sat, Aug 29
Southwest Logo
6:30 am - 1:45 pm
SJU
-
MDW
8h 15m
2 stops
Southwest Logo
7:50 am - 6:05 pm
MDW
-
SJU
9h 15m
2 stops
$296Southwest
Wed, May 27 - Fri, Jun 5
United Airlines Logo
4:12 pm - 11:26 pm
MBJ
-
ORD
7h 14m
1 stop
United Airlines Logo
9:55 pm - 3:10 pm
ORD
-
MBJ
17h 15m
1 stop
$312United Airlines
Wed, Jun 24 - Tue, Jun 30
United Airlines Logo
2:40 pm - 7:59 am
MBJ
-
ORD
17h 19m
1 stop
United Airlines Logo
8:40 am - 3:10 pm
ORD
-
MBJ
6h 30m
1 stop
$316United Airlines
Mon, Aug 24 - Mon, Aug 31
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
6:00 am - 4:35 pm
MDW
-
SJU
9h 35m
1 stop
$326Delta
Useful Info

Good to know

Low seasonMarch
Cheapest flight$112
Best time to beat the crowds but there is an average 36% increase in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from San Juan Airport to Chicago O'Hare 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 8450 reviews
7.8Comfort
8.1Boarding
7.8Entertainment
8.5Crew
7.2Food
Airline reviews

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

6.0 Goodrghinftl, May 2026
FWA - ATL
Read more Delta reviews

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

Every flight was delayed except the last one. One layover turned into two. Travel time extended by three hours. No compensation offered. Repeatedly asked if I'd like to cancel my flight for a partial refund.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Everything could and should be better. We are paying for, it's not a favor, it's a service and should involve quality, responsibility and respect.

Seats were comfortable, 8 hours. One flight attendant was not appropriate in his verbal response: "Please, DON'T touch me.", after being tapped near his elbow after being made unaware he skipped serving me & had passed further down the aisle.

Boarding in Amsterdam is always chaotic. More complicated than needs to be ( boarding pass checked twice, once for general security, then by the airline). The bathrooms on this flight are dirty, and smelly. The food was mediocre at best The crew was decent

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Schererville
Chesterton
Munster
Porter
Monticello
Saint John
Griffith

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.