$105 Find Cheap Flights from Chicago O'Hare Airport to Caribbean - 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 from O'Hare Intl to Caribbean departing on 9/26. 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.
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Cheap Flights from O'Hare Intl to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$375
Santo Domingo
Santo Domingo1 stop$337
Montego Bay
Montego Bay2 stops$419
Oranjestad
Oranjestad1 stop$391
Nassau
Nassau2 stops$360
Kingston
Kingston2 stops$479
Simpson Bay
Simpson Bay1 stop$334
Providenciales
Providenciales1 stop$351
Port of Spain
Port of Spain1 stop$472
Bridgetown
Bridgetown1 stop$365
George Town
George Town1 stop$346
Willemstad
Willemstad1 stop$347
Castries
Castries2 stops$708
Aguadilla
Aguadilla1 stop$356
St. John's
St. John's2 stops$575
Puerto Plata
Puerto Plata1 stop$395
Punta Cana
Punta Cana1 stop$375
Santo Domingo
Santo Domingo1 stop$337
Montego Bay
Montego Bay2 stops$419
Oranjestad
Oranjestad1 stop$391
Nassau
Nassau2 stops$360
Kingston
Kingston2 stops$479
Simpson Bay
Simpson Bay1 stop$334
Providenciales
Providenciales1 stop$351
Port of Spain
Port of Spain1 stop$472
Bridgetown
Bridgetown1 stop$365
George Town
George Town1 stop$346
Willemstad
Willemstad1 stop$347
Castries
Castries2 stops$708
Aguadilla
Aguadilla1 stop$356
St. John's
St. John's2 stops$575
Puerto Plata
Puerto Plata1 stop$395

Book Cheap O'Hare Intl to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Caribbean 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 O'Hare Intl to Caribbean

Thu, Sep 17 - Thu, Sep 24
Frontier Logo
7:11 am - 1:34 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
29h 23m1 stop Fort Lauderdale
Frontier Logo
7:00 am - 2:45 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
8h 45m1 stop Fort Lauderdale
$222Frontier
Sat, Sep 12 - Fri, Sep 18
Frontier Logo
7:11 am - 5:03 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
8h 52m1 stop Fort Lauderdale
Frontier Logo
3:08 am - 2:17 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
12h 09m2 stops Miami Houston George Bush Intcntl
$223Frontier
Sat, Aug 22 - Sat, Aug 29
Multiple Airlines Logo
12:44 am - 6:44 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
5h 00mnonstop
Multiple Airlines Logo
5:00 pm - 11:44 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
7h 44m1 stop Fort Lauderdale
$229Multiple Airlines
Mon, Aug 24 - Tue, Sep 1
American Airlines Logo
5:20 pm - 11:15 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 55mnonstop
American Airlines Logo
12:55 am - 5:00 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 05mnonstop
$247American Airlines
Thu, Aug 20 - Tue, Sep 1
American Airlines Logo
5:20 pm - 11:15 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 55mnonstop
American Airlines Logo
12:55 am - 5:00 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 05mnonstop
$247American Airlines
Sat, Sep 19 - Sat, Sep 26
United Airlines Logo
8:55 am - 2:44 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 49mnonstop
United Airlines Logo
3:56 pm - 8:05 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 09mnonstop
$247United Airlines
Mon, Sep 7 - Sat, Sep 19
United Airlines Logo
8:55 am - 2:44 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 49mnonstop
United Airlines Logo
3:56 pm - 8:05 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 09mnonstop
$247United Airlines
Wed, Aug 26 - Tue, Sep 1
Delta Logo
6:00 am - 4:33 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
9h 33m1 stop New York John F Kennedy Intl
Delta Logo
7:30 am - 5:06 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
10h 36m1 stop New York John F Kennedy Intl
$256Delta
Sat, Aug 29 - Sat, Sep 5
Multiple Airlines Logo
3:20 pm - 11:20 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
7h 00m1 stop Fort Lauderdale
Multiple Airlines Logo
7:14 pm - 11:27 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 13mnonstop
$264Multiple Airlines
Tue, Sep 22 - Tue, Sep 29
Delta Logo
10:25 am - 11:49 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
12h 24m1 stop New York John F Kennedy Intl
Delta Logo
1:16 pm - 9:37 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
9h 21m1 stop New York John F Kennedy Intl
$276Delta
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Caribbean flights

Get data-powered insights and trends into flights from O'Hare Intl to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago O'Hare Intl Airport to Caribbean flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Chicago O'Hare Intl Airport found in the last 5 days was to San Juan, at $191 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $191.

What is the cheapest time of day to fly to Caribbean?

The average price for all round-trip flights from Chicago O'Hare Intl Airport to Caribbean depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $362 on average. Morning departures are around 19% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $522.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Caribbean?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $672, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Caribbean is August, when tickets cost $438 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $610 and $599 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Caribbean?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Caribbean clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago O'Hare Airport to Caribbean, look for departures on Tuesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Caribbean, Thursday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low season

September

Cheapest flight

$105
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chicago O'Hare Airport to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Caribbean?

    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 Chicago O'Hare Airport to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport to Caribbean 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 Chicago O'Hare Airport to Caribbean?

    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 from Chicago O'Hare Airport to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Caribbean?

    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 from Chicago O'Hare Airport to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Caribbean

  • Looking for a cheap flight? 25% of our users found tickets from Chicago O'Hare Airport to the following destinations at these prices or less: San Juan $130 one-way - $315 round-trip

Reviews of the top 5 airlines serving from O'Hare Intl to Caribbean

 
Need help choosing which airline to fly with from O'Hare Intl to Caribbean? 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 10080 reviews
7.1Entertainment
8.1Crew
7.7Boarding
6.7Food
7.3Comfort
Airline reviews

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

2.0 MediocreRichard, Aug 2026
Read more United Airlines reviews

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

gate crew was courteous and helpful, flight attendant was nice and friendly once we got going. But we pushed off from the gate relatively on time, then sat there like 10 ft away, for an hour, with no announcement or explanation. Taxiing then took forever, and I get that there was runway congestion, but would be helpful to keep us posted on whats going on

The power outlets were not working for my row. Also felt like the seats have gotten smaller. I was in the window seat and felt like suffocated, as the two passengers next to me were tall and wide.

Terrible. The flight I booked had a convenient departure time. Quick layover. And an arrival timed that worked for the people who had to pick me up. Thanks to delays and rebooking I got none of those things

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

You did a great job rescheduling my cancelled flight. However, you made me pay for two seats for $118 even though the seats on the original flight were free. I think that was a very unfair thing to do.

They cancelled the flight after 5 hours at the airport and the only flight they offered was for the next day with a 7.5 layover in fll. This was not going to work for me as this was only a weekend trip and getting into providence at 10 pm a day later caused me to lose Mo ey on hotels money on airport parking a dog sitter etc. they wouldn’t offer any type of a voucher or anything else. All they did was refund the flight which didn’t help me with all the money in time I lost. I was going to see my very sick father

The flight was on time the crew was courteous that makes for a good flight.

A more comfortable seat. Padding would be really helpful but I've read the airlines don't want customers to be satisfied with economy seats.

When I booked, I included my checked luggage and when the bill was sent there was no record of this. Its was costly since I am from Trinidad amd Tobago. Exchange rate over seven dollars to one US dollar.

Everything was good except checking bags . I had paid for two bags but it didn’t show so we had to do it again while people waited and we were struggling to get to our flight

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

The seats were roomier than other airplanes I’ve been on.

Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.

Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

The food for sale on board has opportunity for improvement.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports