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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

Tue, Sep 15 - Sat, Sep 19
Frontier Logo
8:45 am - 3:20 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
7h 35m1 stop Fort Lauderdale
Frontier Logo
7:11 am - 5:03 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
8h 52m1 stop Fort Lauderdale
$184Frontier
Fri, Nov 13 - Mon, Nov 16
American Airlines Logo
3:49 pm - 7:27 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 38mnonstop
American Airlines Logo
8:05 am - 2:55 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 50mnonstop
$217American Airlines
Fri, Sep 18 - Fri, Sep 25
Frontier Logo
3:55 pm - 10:59 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
8h 04m1 stop Orlando
Frontier Logo
11:15 am - 11:13 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
10h 58m1 stop Orlando
$217Frontier
Fri, Oct 23 - Mon, Oct 26
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
Thu, Sep 24 - Tue, Sep 29
Southwest Logo
6:00 am - 2:30 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 30m2 stops Tampa Louisville Intl
Southwest Logo
6:15 am - 1:30 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
6h 15m1 stop Orlando
$226Southwest
Thu, Sep 24 - Tue, Sep 29
Southwest Logo
6:00 am - 2:30 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 30m2 stops Tampa Louisville Intl
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
$226Southwest
Tue, Sep 15 - Tue, Sep 22
United Airlines Logo
1:25 pm - 10:15 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
9h 50m1 stop Newark
United Airlines Logo
8:55 am - 2:44 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 49mnonstop
$252United Airlines
Fri, Sep 25 - Sun, Sep 27
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
$252United Airlines
Wed, Sep 16 - Wed, Sep 23
Multiple Airlines Logo
8:45 am - 2:45 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
31h 00m1 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
$270Multiple Airlines
Wed, Oct 21 - Sun, Oct 25
Air Canada Logo
12:30 pm - 9:00 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
20h 30m1 stop Toronto Pearson Intl
Air Canada Logo
10:15 am - 11:50 amORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
25h 35m1 stop Toronto Pearson Intl
$327Air Canada
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Good to know

Low season

March

Cheapest flight

$119
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 10121 reviews
6.7Food
8.1Crew
7.3Comfort
7.1Entertainment
7.7Boarding
Airline reviews

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.

6.0 GoodRaghupathy, Aug 2026
Read more United Airlines reviews

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.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

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

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

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
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