$120 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

Tue, Sep 1 - Mon, Sep 7
Frontier Logo
7:14 pm - 11:27 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 13mnonstop
Frontier Logo
12:44 am - 6:44 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
5h 00mnonstop
$185Frontier
Thu, Sep 3 - Mon, Sep 7
Frontier Logo
7:14 pm - 11:27 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 13mnonstop
Frontier Logo
12:44 am - 6:44 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
5h 00mnonstop
$188Frontier
Thu, Sep 10 - Tue, Sep 15
Southwest Logo
2:35 pm - 9:30 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 55m1 stop Orlando
Southwest Logo
9:40 am - 9:00 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 20m1 stop Orlando
$226Southwest
Thu, Sep 10 - Tue, Sep 15
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 - 4:25 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
9h 10m1 stop Orlando
$226Southwest
Tue, Sep 1 - Sun, Sep 6
American Airlines Logo
12:55 am - 5:00 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 05mnonstop
American Airlines Logo
6:49 am - 12:15 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
16h 26m1 stop Charlotte Douglas
$242American Airlines
Fri, Sep 4 - Tue, Sep 8
American Airlines Logo
12:55 am - 5:00 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 05mnonstop
American Airlines Logo
6:45 am - 10:24 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
14h 39m1 stop Philadelphia
$242American 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
8:55 am - 2:44 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 49mnonstop
$247United Airlines
Fri, Sep 11 - Mon, Sep 21
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
8:55 am - 2:44 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 49mnonstop
$247United Airlines
Tue, Sep 29 - Thu, Oct 1
JetBlue Logo
6:00 am - 7:05 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
14h 05m1 stop Baltimore/Washington
JetBlue Logo
8:40 pm - 9:20 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
11h 40m1 stop Orlando
$247JetBlue
Wed, Oct 21 - Wed, Oct 28
JetBlue Logo
9:00 am - 11:44 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
15h 44m1 stop Fort Lauderdale
JetBlue Logo
7:00 am - 10:09 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
14h 09m1 stop Fort Lauderdale
$256JetBlue
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Good to know

Low season

March

Cheapest flight

$120
Best time to beat the crowds but there is an average 32% increase in price.
Most popular time to fly and prices are also 1% lower on average.
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 10102 reviews
7.7Boarding
6.7Food
7.3Comfort
8.1Crew
7.1Entertainment
Airline reviews

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

6.0 GoodDario, Aug 2026
Read more United Airlines reviews

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.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

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.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

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
Chesterton
Munster
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Caribbean Islands