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Cheap Flights from Chicago to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$401
Santo Domingo
Santo Domingo1 stop$368
Montego Bay
Montego Bay2 stops$478
Oranjestad
Oranjestad1 stop$551
Nassau
Nassau1 stop$392
Kingston
Kingston1 stop$587
Simpson Bay
Simpson Bay1 stop$447
Providenciales
Providenciales1 stop$439
George Town
George Town1 stop$431
Aguadilla
Aguadilla1 stop$250
St. John's
St. John's1 stop$520
Punta Cana
Punta Cana1 stop$401
Santo Domingo
Santo Domingo1 stop$368
Montego Bay
Montego Bay2 stops$478
Oranjestad
Oranjestad1 stop$551
Nassau
Nassau1 stop$392
Kingston
Kingston1 stop$587
Simpson Bay
Simpson Bay1 stop$447
Providenciales
Providenciales1 stop$439
George Town
George Town1 stop$431
Aguadilla
Aguadilla1 stop$250
St. John's
St. John's1 stop$520
Booking Insights

KAYAK's insights & trends for Chicago to Caribbean Islands flights

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

What is the cheapest Chicago to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Chicago found in the last 5 days was to San Juan, at $255 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 $255.

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

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $370 on average. Morning departures are around 22% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $521.

Can I save money by flying with a layover from Chicago to Caribbean Islands?

No, with an average price for the route of $516, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Caribbean Islands?

The cheapest month for flights from Chicago to Caribbean Islands is February, when tickets cost $575 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $732 and $697 respectively.

What’s the cheapest day of the week to fly from Chicago to Caribbean Islands?

If your flying dates are flexible, you should consider flying to Caribbean Islands on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from Chicago to Caribbean Islands. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

How far in advance should I book a flight from Chicago to Caribbean Islands?

To get a below average price on the flight from Chicago to Caribbean Islands, 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
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 4% increase in price.

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Chicago to Caribbean Islands?

    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 to Caribbean Islands.

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

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

    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 to Caribbean Islands 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 to Caribbean Islands?

    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 to 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 5 airlines serving from Chicago to Caribbean Islands

 
Need help choosing which airline to fly with from Chicago to Caribbean Islands? 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.
7.8
DeltaOverall score based on 8699 reviews
7.2Food
7.8Entertainment
8.5Crew
7.8Comfort
8.1Boarding
Airline reviews

No beverage/snack service without any explanation or reason. Late boarding and delayed flight.

4.0 OkayKathryn, Oct 2026
Read more Delta reviews

No beverage/snack service without any explanation or reason. Late boarding and delayed flight.

The cabin and bathroom experience was poor as the cabin and bathroom were dirty and showed signs of an older plane that had not been updated for Customer’s, comfort and health. There was gum on my seat when I arrived and dirt spots around the fan and light controls. The flight was almost entirely full, so there was no way I could be moved from my seat. Th bathroom had the peeling paint.

I'm 6' 2" and even in economy plenty of leg room

Horrible experience. Delta delayed the flight to 11pm which happens. Apparently the pilots were there but we were waiting for flight attendants to arrive from Detroit and they were delayed. They could have made arrangements but that’s fine. What was truly horrible was that at 10:50pm the pilot comes out and says the flight will be cancelled but hasn’t been cancelled yet in the system. It’s being cancelled because the pilots have timed out. As soon as that plane got delayed past 10:50pm delta knew it couldn’t fly. Yet they made us wait around for hours. When the flight finally got cancelled all the area hotels were booked and flights for the next day were unavailable until midday. All I wanted was to spend one day with my family before needing to fly abroad on another delta flight. That will be my last flight with them. I’ll take my 800k miles flown and annual spend to an airline that isn’t so thoughtless.

THI IS THE 3RD CONSECUTIVE FLIGHT FROM ORD TO MSP THAT HAS BEEN DELAYED 2+ HOURS. CRAZY

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Waited on tarmac for approximately 15-25 minutes before taking off. When landing, the time it took to taxi to our gate was the also 15-25 minutes.

Connection times always good online, but not in reality when first leg is delayed (2 out of 2 times this trip).

It was good flight was smooth, little cold on the plane but other wise good.

Great flight and crew. Need more legroom and DO NOT allow seats to recline.

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

We left 1.5 hours late due to a “maintenance” issue. Very poor communication as to when we would board & depart. The crew in First Class was uncharacteristically not friendly). Delay into Brussels cost me my connection to Rome so lost the entire first day of vacation ( had a 10:30am flight to Rome - ended up on a 6:55pm flight).

Everything was OK except the meals, that was overpriced chicken meat.

Miss My connection I had to take a flight from Indianapolis to Denver , then to san fransisco , sleep in sans fransisco en the flight to Los Cabos the next morning

The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.

Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!

The food in first class has taken a big downturn

Flight was fine. Just delays leaving due to mechanical issues. But flight crew were kind and professional. Seats were spacious. American doesn't need to have 9 groups for boarding.

Both departure and return flights had mechanical delays. Their planes are antiquated resulting in a two hour flight taking almost four hours to complete.

Crew were helpful, pilot kept us informed about turbulence, snack choice was awesome!

It was one of the worst I have ever had. The plane was over booked, and I did not have a seat. When I questioned why because I had booked this weeks in advance. I was brushed off to be advised they are trying to find someone to give up their seat. Only to be advised I would be boarding last. I had priority boarding in group 1-4. When I asked why I had to be last because that is not what I paid for I was advised it doesn't matter you will get a seat. The ticket person was very rude and unprofessional. The gate changed several times and it was going from one area to another area far away from where we were at. I feel like I should have been compensated in some kind of way because of the way I was treated. The ticket agent acted like it was my fault that the plane was over booked. Not one time was I apologized to for this inconvenience.

We did not fly on American Airlines from Chicago to London. We were rebooked on British Airways (by American Airlines) and our luggage was left behind. A full day delay and lost luggage.

I have posted the comments in the first flight leg.

First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.

My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.

The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.

I got to the airport and the airline told me i did not have a flight. I never got a confirmation email yet I did get charged. Please refund my money asap

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.

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

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.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental