$96 Find Cheap Flights from Chicago O'Hare Airport to Caribbean

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 5/1. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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$300
Santo Domingo
Santo Domingo1 stop$309
Montego Bay
Montego Bay2 stops$297
Oranjestad
Oranjestad1 stop$402
Nassau
Nassau1 stop$474
Kingston
Kingston1 stop$326
Simpson Bay
Simpson Bay1 stop$254
Providenciales
Providenciales1 stop$380
Port of Spain
Port of Spain1 stop$384
Bridgetown
Bridgetown1 stop$430
George Town
George Town1 stop$345
Willemstad
Willemstad1 stop$372
Castries
Castries2 stops$673
Puerto Plata
Puerto Plata1 stop$510
St. John's
St. John's2 stops$458
Aguadilla
Aguadilla1 stop$221
Punta Cana
Punta Cana1 stop$300
Santo Domingo
Santo Domingo1 stop$309
Montego Bay
Montego Bay2 stops$297
Oranjestad
Oranjestad1 stop$402
Nassau
Nassau1 stop$474
Kingston
Kingston1 stop$326
Simpson Bay
Simpson Bay1 stop$254
Providenciales
Providenciales1 stop$380
Port of Spain
Port of Spain1 stop$384
Bridgetown
Bridgetown1 stop$430
George Town
George Town1 stop$345
Willemstad
Willemstad1 stop$372
Castries
Castries2 stops$673
Puerto Plata
Puerto Plata1 stop$510
St. John's
St. John's2 stops$458
Aguadilla
Aguadilla1 stop$221

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, Apr 16 - Fri, Apr 24
Multiple Airlines Logo
12:42 pm - 10:29 pm
ORD
-
SJU
8h 47m
1 stop
Multiple Airlines Logo
4:34 pm - 8:49 pm
SJU
-
ORD
5h 15mnonstop
$223Multiple Airlines
Fri, Apr 24 - Mon, Apr 27
Multiple Airlines Logo
2:09 pm - 11:43 pm
ORD
-
SJU
8h 34m
1 stop
Multiple Airlines Logo
2:59 am - 1:00 pm
SJU
-
ORD
11h 01m
1 stop
$224Multiple Airlines
Thu, Apr 16 - Tue, Apr 21
Multiple Airlines Logo
12:42 pm - 10:29 pm
ORD
-
SJU
8h 47m
1 stop
Multiple Airlines Logo
2:00 pm - 8:05 am
SJU
-
ORD
19h 05m
1 stop
$225Multiple Airlines
Mon, Apr 13 - Wed, Apr 15
Spirit Airlines Logo
12:45 pm - 9:59 pm
ORD
-
SJU
8h 14m
1 stop
Spirit Airlines Logo
10:59 am - 3:08 pm
SJU
-
ORD
5h 09mnonstop
$226Spirit Airlines
Thu, Apr 30 - Wed, May 6
Spirit Airlines Logo
7:15 pm - 7:22 pm
ORD
-
SJU
23h 07m
1 stop
Spirit Airlines Logo
11:01 am - 3:11 pm
SJU
-
ORD
5h 10mnonstop
$227Spirit Airlines
Thu, May 7 - Mon, May 11
Multiple Airlines Logo
4:44 pm - 10:21 pm
ORD
-
SJU
4h 37mnonstop
Multiple Airlines Logo
6:00 am - 11:13 pm
SJU
-
ORD
18h 13m
1 stop
$228Multiple Airlines
Sat, May 2 - Tue, May 5
Frontier Logo
1:27 pm - 12:23 pm
ORD
-
SJU
21h 56m
1 stop
Frontier Logo
6:00 am - 11:13 pm
SJU
-
ORD
18h 13m
1 stop
$230Frontier
Mon, May 4 - Fri, May 8
Frontier Logo
4:58 pm - 12:11 pm
ORD
-
MBJ
19h 13m
2 stops
Frontier Logo
1:16 pm - 7:55 am
MBJ
-
ORD
18h 39m
1 stop
$297Frontier
Sat, May 9 - Sat, May 16
United Airlines Logo
8:40 am - 12:50 pm
ORD
-
MBJ
4h 10mnonstop
United Airlines Logo
1:52 pm - 6:15 pm
MBJ
-
ORD
4h 23mnonstop
$318United Airlines
Mon, May 18 - Thu, May 21
American Airlines Logo
5:00 am - 2:15 pm
ORD
-
MBJ
9h 15m
1 stop
American Airlines Logo
2:30 pm - 7:15 pm
MBJ
-
ORD
4h 45mnonstop
$322American Airlines
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 72 hours was to San Juan, at $229 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 72 hours was $229.

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 $380 on average. Morning departures are around 12% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $491.

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 $643, 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 September, when tickets cost $309 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $524 and $442 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, Friday 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 seasonSeptember
Cheapest flight$96
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chicago O'Hare Airport to Oranjestad

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.

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 9548 reviews
8.1Crew
6.6Food
7.7Boarding
7.1Entertainment
7.3Comfort
Airline reviews

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

10.0 ExcellentNan, Apr 2026
ORD - FRA
Read more United Airlines reviews

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

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

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

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

Paid for WiFi and the connection was basically nonexistent. Was pleasantly surprised with everything else. Staff was great. Boarding was easy. Plane was clean. Overall, a very pleasant experience

Long long delay, no AC while delayed, gate changes, just for the most uncomfortable flight of your life.

Everything was smooth sailing. Great crew, easy flight and was surprised with an upgraded seat. Thank you all!

My first time experience with Spirit Air was not good at all.The reason i did not know to cancel 24Hrs before flight depature you do charge cancellation fee. It's ridiculous policy.Actually you should provide full voucher instead of charging cancellation fee. Confirmation Code# ZNVPHG Thanks Much , Rita S

I truly admired that the last minute flight attendants were willing to come to serve flight # 1465 and think they should be extra compensated. Doesn't have to beonetary a star a permanent position with Spirit as long as she flies etc. They were o so pleasant and accommodating. 😊😊. Please also serve water. Plain unadulterated water 💧! Invest in a filter of your own the cost of bottles are a penny on the dollar and you could have a plug on advertising with labeling. This could be hilarious "WATER TO REFREST THE SPIRIT FROM SPIRIT ITSELF!" - Free idea!😄😄😄. Anyway overall, though a tad late the flight met expectations. Thanks you Spirit, for everything.

We were delayed and the bag charge fees are very expensive.

The worst. My flight was canceled :-- by email! -- at 10pm, just 8 hours prior to departure. Normally, given the early departure time, I would've been asleep. I was lucky to be awake and to be able to take action. Even worse, it turns out that the flight wasn't canceled (confirmed because I was at the airport and saw it loading), Spirit just canceled my reservation, probably because I got such a good rate! Utterly appalling. Notably, Spirit did not inform you (Kayak) of the change, so I kept getting alerts from you.

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

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 !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports