
Cheap Flights from Chicago to Caribbean Islands
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysKAYAK'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 $226 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 $226.
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 $363 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 $524.
Can I save money by flying with a layover from Chicago to Caribbean Islands?
No, with an average price for the route of $501, 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 January, when tickets cost $546 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $697 and $691 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.
Which airlines fly non-stop between Chicago and Caribbean Islands?
There are 8 airlines that fly nonstop from Chicago to Caribbean Islands. They are: American Airlines, Frontier, JetBlue, Southwest, Hahn Air, Arajet, WorldTicket and United Airlines. The cheapest price of all airlines flying this route was found with Frontier at $91 for a round-trip flight to San Juan Luis Munoz Marin Intl Airport (SJU). On average, Arajet offers the best prices for nonstop flights between Chicago and Caribbean Islands.
Which airlines fly most frequently between Chicago and Caribbean Islands?
Chicago and Caribbean Islands are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (14 flights per week), United Airlines (9 flights per week), and Air Canada (7 flights per week).
Which cabin class options are there for flights between Chicago and Caribbean Islands?
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.
How many flights are there between Chicago and Caribbean Islands per day?
Each day, there are between 3 and 6 nonstop flights that take off from Chicago and land in Caribbean Islands, with an average flight time of 4h 41m. The most common departure time is 8:00 am and most flights take off in the morning, while the most flights land at Punta Cana. Each week, there are 27 flights. The most frequent day of departure is Sunday, when 22% of all weekly flights depart. The fewest flights depart on a Tuesday.
What’s the earliest departure time from Chicago to Caribbean Islands?
The earliest flight from Chicago to Caribbean Islands departs at 8:05 am, landing in San Juan at 2:55 pm.
What’s the latest departure time from Chicago to Caribbean Islands?
If you prefer to fly at night, the latest flight from Chicago to Caribbean Islands jets off at 2:16 pm and lands in San Juan at 8:00 pm.
Good to know
Low season | September |
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High season | March |
FAQs - booking Caribbean Islands flights
Reviews of the top 5 airlines serving from Chicago to Caribbean Islands
No beverage/snack service without any explanation or reason. Late boarding and delayed flight.
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.
The seats are very small, that is all the staff did a good job.
It was great. The staff is always helpful and polite. The app is great and makes the whole trip and process so easy. They even offer a step to step guide to your correct terminal. And they keep all the information you'll need updated. Anything you can think of! Great experience.
Perfect. On time and the weather was perfect so we came in a few minutes early.
On time. Carry on and personal bag was accommodated on the plane. Entertainment was accessible without bringing own device. Whole can of juice was provided rather than a pour.
Price was crazy watch it if you Chan he your flight
On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.
Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s
No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.
Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late
Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.
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.
After boarding, the AC was shut off on the flight. At business class, I really could not breathe. I was absolutely dripping sweat. I was told by the FA that there was nothing they could do but I could stand by the door until departure. So, that's what I did. I was clearly in the way while the FAs were trying to do their work, but I had to be able to breathe. After that, of course, I had sweated up a lot so was very uncomfortable for the six hour flight.
DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.
AA was fine....the overall experience was subpar, but not due to the airline due to broader issues
No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.
Check-in process was poor, very poor, only one person to check-in all passengers, so if one passenger had a check-in issue, all other passengers were delayed. All check-ins should have two airline staff to check-in passengers.
The flight up was great no issues. The flight back home was a cluster. I was told the plane I was waiting on was giving to another flight which caused me to miss my connection flight. Granted the airline did great with getting hotel and vouchr for food.
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.
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
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.