$119 Find Cheap Flights from Caribbean Islands to Chicago - Compare and Save

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 8/13. 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

Wed, Jul 22 - Mon, Aug 10
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$235Frontier
Fri, Aug 28 - Tue, Sep 1
Frontier Logo
6:45 am - 1:00 pm
SJU
-
ORD
31h 15m
1 stop
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$236Frontier
Sat, Sep 5 - Tue, Sep 8
United Airlines Logo
3:56 pm - 8:05 pm
SJU
-
ORD
5h 09mnonstop
United Airlines Logo
8:55 am - 2:44 pm
ORD
-
SJU
4h 49mnonstop
$237United Airlines
Thu, Aug 20 - Sun, Aug 23
American Airlines Logo
7:24 pm - 7:34 am
SJU
-
ORD
13h 10m
1 stop
American Airlines Logo
5:20 pm - 11:15 pm
ORD
-
SJU
4h 55mnonstop
$242American Airlines
Wed, Aug 19 - Mon, Aug 24
Delta Logo
12:56 pm - 10:36 pm
SJU
-
MDW
10h 40m
1 stop
Delta Logo
6:05 am - 1:42 pm
MDW
-
SJU
6h 37m
1 stop
$246Delta
Wed, Aug 26 - Sat, Aug 29
Delta Logo
12:56 pm - 10:36 pm
SJU
-
MDW
10h 40m
1 stop
Delta Logo
6:05 am - 4:38 pm
MDW
-
SJU
9h 33m
1 stop
$256Delta
Wed, Aug 19 - Fri, Aug 21
Southwest Logo
8:20 am - 4:55 pm
SJU
-
MDW
9h 35m
2 stops
Southwest Logo
1:00 pm - 10:50 pm
MDW
-
SJU
8h 50m
2 stops
$286Southwest
Thu, Sep 17 - Mon, Sep 21
Southwest Logo
8:55 pm - 11:25 am
SJU
-
MDW
15h 30m
2 stops
Southwest Logo
1:00 pm - 11:50 pm
MDW
-
SJU
9h 50m
2 stops
$291Southwest
Fri, Sep 4 - Sun, Sep 13
American Airlines Logo
2:12 pm - 6:55 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
6:00 am - 12:53 pm
ORD
-
MBJ
6h 53m
1 stop
$326American Airlines
Sat, Jul 4 - Sun, Aug 16
United Airlines Logo
2:40 pm - 7:59 am
MBJ
-
ORD
17h 19m
1 stop
United Airlines Logo
6:00 am - 3:10 pm
ORD
-
MBJ
9h 10m
1 stop
$331United Airlines
Useful Info

Good to know

Low seasonMarch
Cheapest flight$119
Best time to beat the crowds but there is an average 45% 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.
7.8
DeltaOverall score based on 8432 reviews
7.8Comfort
8.5Crew
8.1Boarding
7.8Entertainment
7.2Food
Airline reviews

Love me some Delta. One of the few airlines to recognize and support veterans. Easy boarding, flight was on time and arrived early and the flight attendants were excellent on this flight.

10.0 ExcellentAnonymous, Jun 2026
SEA - LAX
Read more Delta reviews

Love me some Delta. One of the few airlines to recognize and support veterans. Easy boarding, flight was on time and arrived early and the flight attendants were excellent on this flight.

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

Very good flight. Crew was great. No issues and we even arrived early.

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

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

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

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
Munster
Chesterton
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.