$98 Find Cheap Flights from Chicago to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Caribbean Islands departing on 9/20. 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

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Caribbean Islands.
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Cheap Flights from Chicago to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cananonstop$303
Santo Domingo
Santo Domingo1 stop$240
Montego Bay
Montego Bay1 stop$395
Oranjestad
Oranjestad1 stop$395
Nassau
Nassau1 stop$412
Simpson Bay
Simpson Bay1 stop$296
Kingston
Kingston1 stop$359
Providenciales
Providenciales1 stop$448
George Town
George Town1 stop$357
St. John's
St. John's1 stop$475
Aguadilla
Aguadilla1 stop$260
Punta Cana
Punta Cananonstop$303
Santo Domingo
Santo Domingo1 stop$240
Montego Bay
Montego Bay1 stop$395
Oranjestad
Oranjestad1 stop$395
Nassau
Nassau1 stop$412
Simpson Bay
Simpson Bay1 stop$296
Kingston
Kingston1 stop$359
Providenciales
Providenciales1 stop$448
George Town
George Town1 stop$357
St. John's
St. John's1 stop$475
Aguadilla
Aguadilla1 stop$260

Book Cheap Chicago to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Caribbean Islands 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 Chicago to Caribbean Islands

Sat, Oct 11 - Fri, Oct 17
Frontier Logo
6:40 am - 3:24 pmORD-SJU
7h 44m1 stop
Frontier Logo
3:40 am - 3:39 pmSJU-ORD
12h 59m1 stop
$216Frontier
Find Deal
Sun, Aug 31 - Fri, Sep 5
Spirit Airlines Logo
5:05 am - 9:48 pmORD-SJU
15h 43m1 stop
Spirit Airlines Logo
7:40 pm - 11:56 pmSJU-ORD
5h 16mnonstop
$220Spirit Airlines
Find Deal
Mon, Oct 13 - Wed, Oct 22
American Airlines Logo
8:35 am - 2:05 pmORD-PUJ
4h 30mnonstop
American Airlines Logo
3:21 pm - 7:36 pmPUJ-ORD
5h 15mnonstop
$338American Airlines
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Tue, Oct 7 - Fri, Oct 10
American Airlines Logo
5:20 am - 3:29 pmORD-PUJ
9h 09m1 stop
American Airlines Logo
3:21 pm - 7:36 pmPUJ-ORD
5h 15mnonstop
$342American Airlines
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Sun, Oct 26 - Fri, Oct 31
Delta Logo
7:59 pm - 2:31 pmORD-PUJ
17h 32m1 stop
Delta Logo
2:49 pm - 11:58 pmPUJ-ORD
10h 09m1 stop
$343Delta
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Mon, Oct 6 - Fri, Oct 10
Southwest Logo
7:05 am - 2:30 pmMDW-PUJ
6h 25m1 stop
Southwest Logo
3:30 pm - 10:20 pmPUJ-MDW
7h 50m1 stop
$343Southwest
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Mon, Oct 27 - Tue, Oct 28
Delta Logo
5:20 am - 1:24 pmORD-PUJ
7h 04m1 stop
Delta Logo
1:53 pm - 7:50 amPUJ-ORD
18h 57m2 stops
$347Delta
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Tue, Sep 23 - Tue, Sep 30
Southwest Logo
6:15 am - 2:10 pmMDW-SJU
6h 55m1 stop
Southwest Logo
8:00 am - 3:10 pmSJU-MDW
8h 10m2 stops
$357Southwest
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Tue, Dec 2 - Sat, Dec 6
United Airlines Logo
6:00 am - 1:33 pmORD-NAS
6h 33m1 stop
United Airlines Logo
4:05 pm - 7:02 pmNAS-ORD
3h 57mnonstop
$464United Airlines
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Fri, Nov 28 - Thu, Dec 4
United Airlines Logo
6:20 pm - 11:50 amORD-NAS
16h 30m1 stop
United Airlines Logo
2:55 pm - 9:07 pmNAS-ORD
7h 12m1 stop
$474United Airlines
Find Deal
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?

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

The cheapest ticket to Caribbean Islands from Chicago found in the last 72 hours was to Punta Cana, at $192 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 $208.

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

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 $929, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Caribbean Islands, 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 to Caribbean Islands is September, when tickets cost $305 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $561 and $438 respectively.

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

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

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

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Caribbean Islands, 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 to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$98
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Chicago O'Hare Airport to Montego Bay

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.

  • 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 $306 on average. Morning departures are around 12% 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 $444.

Reviews of the top 5 airlines serving from Chicago to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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.
7.9
DeltaOverall score based on 7982 reviews
8.2Boarding
7.9Entertainment
7.9Comfort
7.3Food
8.5Crew
Airline reviews

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

6.0 GoodKristopher, Aug 2025HPN - ATL
Read more Delta reviews

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

There was supposed to be a meal served, but there wasn’t and the major toilet was out of order

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

The staff was very very rude in Las Vegas when boarding the flight. When presenting the boarding ticket. Las Vegas flight, it was hot and stuffy, it smelled really bad.

Dear All, I have harassment and accident with the flight attendant . This is my phone to talk 8168073567, please, leave phone message . Regards Emily,

The incoming plane ✈️ was delayed 5 hours en route to Raleigh. My flight was delayed for 5 hours 😢. Finally boarded and then de boarded due to an AC problem. A very tough and long night.

Flight was on time but the amount of noise from several children and the kicking of my seat the entire flight was overwhelming.

I liked the check in procedure. The luggage charges and overweight cost can be better.

The flight was delayed be over 3 hours. I tried to get a refund for Vivian Kirby and my session kept being stopped. I was NEVER able to finish the prosses...after 2 hours of attempting.

Again, when I use Kayak I expect to pay the total amount and that´s it. Someone added an additional charge few days later after purchasing the tickets.

My experience with Spirit was good, but the experience with Kayak was not. Based on the Spirit agent Kayak added an additional charge after purchasing the tickets. When I buy the tickets I paid the total amount and I only pay once. This time they added an additional charge because based on Spirit they partially charge the tickets and I still needed to pay a second time. This is not good at all and Unprofessional

Spirit gets such a bad rap. I have never had a bad experience with them and the crew is always friendly and funny. This trip I had knee replacement surgery surgery 10 weeks ago. It is still a little rough to get get from point a to point b. And Spirit was on top of it. When there was a seat available the stewardess asked me if I wanted to move to an open seat so I could elevate my leg on the empty seat? 5 stars all around. They helped me on and helped me off the plane. I can’t say enough about the crew!!

We liked the woman who worked our gate and waited with us for our plane. We changed gates 3 times. Our flight was supposed to leave at 11:28am. We actually left after 5pm. It was not a good situation. This delay cost us a lot of money.

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

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides

Everything you need to know for your flight to Caribbean Islands

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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