$94 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 4/11. 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 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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Flight Deals

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 Cana2 stops$296
Santo Domingo
Santo Domingo1 stop$277
Montego Bay
Montego Bay1 stop$295
Oranjestad
Oranjestad3 stops$425
Nassau
Nassau2 stops$471
Kingston
Kingston1 stop$313
Simpson Bay
Simpson Bay1 stop$253
Providenciales
Providenciales1 stop$371
George Town
George Town1 stop$346
St. John's
St. John's1 stop$507
Aguadilla
Aguadilla1 stop$221
Punta Cana
Punta Cana2 stops$296
Santo Domingo
Santo Domingo1 stop$277
Montego Bay
Montego Bay1 stop$295
Oranjestad
Oranjestad3 stops$425
Nassau
Nassau2 stops$471
Kingston
Kingston1 stop$313
Simpson Bay
Simpson Bay1 stop$253
Providenciales
Providenciales1 stop$371
George Town
George Town1 stop$346
St. John's
St. John's1 stop$507
Aguadilla
Aguadilla1 stop$221

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

Mon, Apr 20 - Sun, Apr 26
Frontier Logo
12:20 pm - 10:29 pm
ORD
-
SJU
9h 09m
1 stop
Frontier Logo
11:30 am - 11:59 pm
SJU
-
ORD
13h 29m
1 stop
$211Frontier
Fri, Apr 17 - Sat, Apr 18
Frontier Logo
9:14 am - 3:37 pm
MDW
-
SJU
29h 23m
1 stop
Frontier Logo
3:21 am - 8:04 am
SJU
-
MDW
29h 43m
1 stop
$211Frontier
Tue, May 26 - Fri, May 29
Frontier Logo
12:40 pm - 4:49 am
ORD
-
SJU
15h 09m
1 stop
Frontier Logo
6:00 am - 12:37 pm
SJU
-
ORD
7h 37m
1 stop
$212Frontier
Sat, Apr 11 - Thu, Apr 16
Spirit Airlines Logo
12:45 pm - 9:59 pm
ORD
-
SJU
8h 14m
1 stop
Spirit Airlines Logo
12:57 pm - 8:05 am
SJU
-
ORD
20h 08m
2 stops
$214Spirit Airlines
Thu, Apr 16 - Thu, Apr 30
Spirit Airlines Logo
7:50 am - 12:58 am
ORD
-
SJU
16h 08m
1 stop
Spirit Airlines Logo
4:34 pm - 8:49 pm
SJU
-
ORD
5h 15mnonstop
$215Spirit Airlines
Mon, Apr 13 - Thu, Apr 16
Arajet Logo
4:30 am - 10:15 am
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
$298Arajet
Sat, Aug 29 - Thu, Sep 3
Arajet Logo
12:12 pm - 5:57 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
7:30 pm - 11:40 pm
PUJ
-
ORD
5h 10mnonstop
$300Arajet
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
Sat, May 9 - Sat, May 16
United Airlines Logo
5:30 am - 1:30 pm
ORD
-
MBJ
8h 00m
1 stop
United Airlines Logo
1:52 pm - 6:15 pm
MBJ
-
ORD
4h 23mnonstop
$322United Airlines
Wed, Aug 12 - Wed, Aug 19
American Airlines Logo
6:34 am - 1:58 pm
ORD
-
MBJ
7h 24m
1 stop
American Airlines Logo
2:00 pm - 6:30 pm
MBJ
-
ORD
4h 30mnonstop
$327American Airlines
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 San Juan, at $216 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 $216.

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

The average price for all round-trip flights from Chicago to Caribbean Islands 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 Islands is generally at night, when round-trip flights cost $376 on average. Morning departures are around 11% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $489.

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 $424, 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 October, when tickets cost $348 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $541 and $447 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 Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Chicago to Caribbean Islands. For your return ticket, we recommend flying on a Friday and avoiding Sundays 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 9 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$94
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Chicago O'Hare Airport to George Town

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

 
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 8359 reviews
7.8Entertainment
7.2Food
8.1Boarding
7.9Comfort
8.5Crew
Airline reviews

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

10.0 ExcellentAnonymous, Mar 2026
SAT - LAX
Read more Delta reviews

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

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

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

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.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Nothing. We didn’t even have a pilot until one hour after our flight was set to depart and now we are waiting for a gate on a very hot packed aircraft. Spirit has lost its goddamn minds and we will never fly again. On the way down the delay went from 5 minutes to 6 hours to cancelled.

We had to take a bus to the plane with a old woman and carry on bags, and at landing at the airport we have to wait one hour seating on the plane waiting for a gate. We came back from Australia Bussines class Quantas 16 hours traveling, then wait in Dallas 7 hours for connection...honestly waiting 1 hour more at the plane was the worst part.

Flight delayed twice (not Spirit fault) No food served* No entertainment * *in response to my choices in the rating. None was provided so couldn’t rate properly

Delayed over two hours. Only knew about a 30 minute delay in advance

Poor service but I guess that’s what you get for picking cheap flight. Overacted with all extra up-charge fees, so annoying.

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.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

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.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

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.