$115 Find Cheap Flights from Caribbean Islands to Chicago - Compare and Save

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Cheap Flights from Caribbean Islands to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean Islands to Chicago

Sat, Oct 17 - Mon, Oct 19
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:15 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 51m1 stop Atlanta Hartsfield-Jackson
$212Frontier
Mon, Oct 12 - Wed, Oct 14
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:21 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 45m1 stop Atlanta Hartsfield-Jackson
$212Frontier
Fri, Oct 23 - Sat, Oct 24
United Airlines Logo
1:25 pm - 10:28 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
10h 03m1 stop Newark
United Airlines Logo
8:55 am - 2:44 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 49mnonstop
$216United Airlines
Thu, Oct 29 - Mon, Nov 2
United Airlines Logo
7:25 am - 11:47 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 22mnonstop
United Airlines Logo
2:16 pm - 9:00 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 44mnonstop
$217United Airlines
Thu, Nov 5 - Mon, Nov 9
American Airlines Logo
3:52 pm - 7:30 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 38mnonstop
American Airlines Logo
7:50 pm - 10:45 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
12h 55m1 stop Miami
$222American Airlines
Thu, Oct 22 - Sat, Oct 31
American Airlines Logo
2:53 pm - 7:29 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 36mnonstop
American Airlines Logo
5:29 pm - 10:45 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
16h 16m1 stop Miami
$222American Airlines
Fri, Dec 4 - Mon, Dec 7
Delta Logo
7:00 am - 5:19 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
12h 19m1 stop New York John F Kennedy Intl
Delta Logo
6:00 am - 4:55 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
8h 55m1 stop New York John F Kennedy Intl
$230Delta
Thu, Oct 29 - Mon, Nov 2
Delta Logo
6:45 am - 5:20 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
11h 35m1 stop New York John F Kennedy Intl
Delta Logo
1:50 pm - 12:52 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
9h 02m1 stop New York John F Kennedy Intl
$230Delta
Fri, Sep 25 - Tue, Sep 29
Southwest Logo
10:00 am - 6:00 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 00m1 stop Orlando
Southwest Logo
6:15 am - 1:30 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
6h 15m1 stop Orlando
$246Southwest
Thu, Sep 24 - Tue, Sep 29
Southwest Logo
10:00 am - 6:00 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 00m1 stop Orlando
Southwest Logo
12:45 pm - 10:05 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 20m2 stops Cincinnati Cinci./N. Kentucky Baltimore/Washington
$246Southwest
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Good to know

Low season

March

Cheapest flight

$115
Best time to beat the crowds but there is an average 33% increase in price.
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 airlines flying 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.
7.4
United AirlinesOverall score based on 10194 reviews
7.3Comfort
8.1Crew
7.1Entertainment
7.7Boarding
6.7Food
Airline reviews

The counter person at the gate was rude and demeaning, to the point that I wouldn't fly this airline again.

2.0 MediocreAnonymous, Sep 2026
Read more United Airlines reviews

The counter person at the gate was rude and demeaning, to the point that I wouldn't fly this airline again.

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

Awful. Delay after delay. And then again on the tarmac.

Kept changing the takeoff time and the moved it up so arrived when boarding had already started. Then sat waiting to taxi in for a long time

Food was not Good Nuts came very wet & not tasting Good Main course I asked for Steak they got me Chicken because they don’t have more !!!!

It cancelled and we were unable to catch our connecting international flights.

Leaving at 7 when scheduled to leave at 4:20 - you tell me. Understood there was a ground stop. Then having to "reboot" the plane because of a lighting strike, also understood. But basically the flight was a "clusterf#$%".

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

ok, butt flght was delyed for 2,5h from Frankfurt, and next Flight to Columbuse same

Flight was great. Almost miss my connecting flight due to late departure from Haneda. Had to run all through airport in Chicago to make the flight. Experience was great for 1st time flyers using ANA Airlines.

Our flight from Chicago to Des Moines was the problem flight due to a dismissive flight attendant. His conduct was unnecessary and unprofessional.. I will avoid using Americam Airlines again because of the situation. Very disappointing.

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

Mechanical issues and delays. I get it but bad experience. Turned my 3 hour airport experience into a 9 hours

The baggage process at the gate was terrible. Stay was not friendly at all

Flight was delayed because of mechanical. Could not get landing space which caused me to miss my connection. Messy and not organized.

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Little bit of trouble getting my KTN and pre-check status onto the ticket, but otherwise the counter staff were friendly and truly concerned to get it right.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Missed connection from delays and times changing multiple times and then involuntarily booked on another airline next day

Traveling to a place near Chicago?

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

More options for your flight to Chicago