$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

Wed, Sep 16 - Wed, Oct 7
Frontier Logo
8:45 am - 2:45 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
31h 00m1 stop Fort Lauderdale
Frontier Logo
7:11 am - 1:31 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
29h 20m1 stop Fort Lauderdale
$196Frontier
Thu, Sep 24 - Sat, Oct 24
Frontier Logo
7:00 am - 2:45 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
8h 45m1 stop Fort Lauderdale
Frontier Logo
8:04 am - 1:31 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
28h 27m1 stop Fort Lauderdale
$197Frontier
Sat, Oct 10 - Sat, Oct 24
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
8:13 am - 2:03 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 50mnonstop
$217American Airlines
Wed, Oct 14 - Sat, Oct 17
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
8:13 am - 2:03 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 50mnonstop
$217American Airlines
Wed, Sep 30 - Tue, Oct 6
Southwest Logo
5:15 am - 12:05 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 50m2 stops Orlando Atlanta Hartsfield-Jackson
Southwest Logo
3:20 pm - 11:10 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
6h 50m1 stop Baltimore/Washington
$226Southwest
Sat, Sep 26 - Thu, Oct 29
Southwest Logo
6:25 am - 4:45 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
11h 20m2 stops Orlando Philadelphia
Southwest Logo
12:45 pm - 12:10 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 25m1 stop Baltimore/Washington
$246Southwest
Wed, Sep 16 - Wed, Oct 7
Multiple Airlines Logo
4:39 pm - 2:45 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
23h 06m2 stops Tampa Fort Lauderdale
Multiple Airlines Logo
7:11 am - 1:31 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
29h 20m1 stop Fort Lauderdale
$266Multiple Airlines
Thu, Sep 24 - Wed, Oct 7
Multiple Airlines Logo
7:00 am - 2:45 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
8h 45m1 stop Fort Lauderdale
Multiple Airlines Logo
7:11 am - 11:58 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
15h 47m2 stops Fort Lauderdale Tampa
$273Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
United Airlines Logo
3:56 pm - 8:05 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 09mnonstop
United Airlines Logo
5:00 am - 1:45 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
7h 45m1 stop Newark
$282United Airlines
Fri, Sep 25 - Mon, Sep 28
United Airlines Logo
3:56 pm - 8:05 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 09mnonstop
United Airlines Logo
5:00 am - 1:45 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
7h 45m1 stop Newark
$282United Airlines
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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 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 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 10146 reviews
7.7Boarding
8.1Crew
7.3Comfort
7.1Entertainment
6.7Food
Airline reviews

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 !!!!

2.0 MediocreRafik, Aug 2026
Read more United Airlines reviews

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.

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Seats are complete BS for 10 hrs. The guy at counter canceled our return flight from europe. Lufthansa on the way back made United look like a trailer park gathering. If given the opportunity, I will never fly united again. Lufthansa seats werent much better to be fair but the service was a 10 out of 10. Incant express how difficult umited made my trip.

It was a great experience to fly with ANA, the sit is very comfortable.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

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

The flight was delayed in 30 minute increments for a total of 4 hours and 30 minute delay. All other flights to Chicago left on time except for this one flight. If there is an issue with the inbound flight, just let customers know so they can find another flight right away, Once we got on the plane there was another 30 minute delay taking off at 10:30 at night which is very unusual that a flight wouldn't be ready to take off

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

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Caribbean Islands