$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 3/11. 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.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

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

Bundle and saveSave money when you bundle your flight + hotel.

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

Flight Deals
Booking Insights
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 Cananonstop$289
Santo Domingo
Santo Domingo1 stop$301
Montego Bay
Montego Baynonstop$294
Oranjestad
Oranjestad3 stops$386
Nassau
Nassau1 stop$470
Kingston
Kingston1 stop$366
Simpson Bay
Simpson Bay1 stop$308
Providenciales
Providenciales1 stop$341
George Town
George Town1 stop$447
St. John's
St. John's2 stops$471
Aguadilla
Aguadilla1 stop$221
Punta Cana
Punta Cananonstop$289
Santo Domingo
Santo Domingo1 stop$301
Montego Bay
Montego Baynonstop$294
Oranjestad
Oranjestad3 stops$386
Nassau
Nassau1 stop$470
Kingston
Kingston1 stop$366
Simpson Bay
Simpson Bay1 stop$308
Providenciales
Providenciales1 stop$341
George Town
George Town1 stop$447
St. John's
St. John's2 stops$471
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, May 4 - Fri, May 8
Spirit Airlines Logo
7:50 am - 2:06 am
ORD
-
SJU
17h 16m
1 stop
Spirit Airlines Logo
12:57 pm - 12:24 am
SJU
-
ORD
12h 27m
1 stop
$188Spirit Airlines
Mon, May 11 - Sun, May 17
Spirit Airlines Logo
5:05 am - 7:22 pm
ORD
-
SJU
13h 17m
1 stop
Spirit Airlines Logo
3:21 am - 1:05 pm
SJU
-
ORD
10h 44m
1 stop
$189Spirit Airlines
Mon, May 4 - Thu, May 7
Spirit Airlines Logo
7:50 am - 2:06 am
ORD
-
SJU
17h 16m
1 stop
Spirit Airlines Logo
3:21 am - 1:05 pm
SJU
-
ORD
10h 44m
1 stop
$193Spirit Airlines
Wed, Apr 8 - Thu, Apr 9
Frontier Logo
2:56 pm - 12:52 am
MDW
-
SJU
8h 56m
1 stop
Frontier Logo
11:01 am - 9:21 pm
SJU
-
MDW
11h 20m
1 stop
$197Frontier
Sat, Apr 11 - Sat, Apr 18
Frontier Logo
8:45 am - 6:49 pm
ORD
-
SJU
9h 04m
1 stop
Frontier Logo
3:47 pm - 10:39 pm
SJU
-
ORD
7h 52m
1 stop
$202Frontier
Mon, Apr 6 - Sat, Apr 18
Arajet Logo
4:30 am - 10:15 am
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 9:57 am
PUJ
-
ORD
5h 10mnonstop
$289Arajet
Mon, Apr 6 - 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
$290Arajet
Wed, Apr 29 - Mon, May 4
American Airlines Logo
8:05 am - 12:13 pm
ORD
-
MBJ
4h 08mnonstop
American Airlines Logo
12:25 pm - 8:30 am
MBJ
-
ORD
20h 05m
1 stop
$294American Airlines
Sat, Apr 18 - Mon, Apr 27
American Airlines Logo
8:05 am - 12:13 pm
ORD
-
MBJ
4h 08mnonstop
American Airlines Logo
4:37 pm - 12:11 pm
MBJ
-
ORD
19h 34m
1 stop
$295American Airlines
Sun, Apr 19 - Thu, Apr 23
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
$298United 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 $174 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 $174.

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 $413, 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 $446 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, 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 2 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$94
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 3% 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.

  • 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 $352 on average. Morning departures are around 10% 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 $481.

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 8268 reviews
7.2Food
7.8Entertainment
8.1Boarding
7.9Comfort
8.5Crew
Airline reviews

Good flight. Connector flight was delayed so made a short turnaround in Atlanta which was stressful. Otherwise, great crew, Staff in ATL was very informative about the delay and ensured people their connections were fine. Notified the ones that were not. Great communication.

10.0 ExcellentDavid, Mar 2026
CVG - ATL
Read more Delta reviews

Good flight. Connector flight was delayed so made a short turnaround in Atlanta which was stressful. Otherwise, great crew, Staff in ATL was very informative about the delay and ensured people their connections were fine. Notified the ones that were not. Great communication.

The flight went very well, but the flight attendants didn't serve and food or drinks other than 1st class due to rough air but to be honest it wasn't that bumpy and I felt that they could've at least offered water and coffee perhaps. Also serving 1st class only is a bad look. I've been in 1st class many times and I would've felt that if the turbulence was too rough for the main cabin, it would be too rough for 1st class too.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

My seatback screen didn’t work so that sucked because that’s what I was going to do on the plane.

Left a few minutes early. Got in 15 minutes early. Very attentive service on board. Very organized boarding.

The whole experience was excellent. As it most often is with Delta

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

I was happy that I was able to get a last minute flight but unfortunately my seat was a middle seat. Even with Delta Comfort I wasn't comfortable

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

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...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

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?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

They changed our boarding gates at the last minute! No one at gate told us! It was finally announced over loud speaker but the person spoke very broken English and couldn’t understand!! Just went to information board to confirm. Had a “ medical emergency “ they called it and we couldn’t use bathrooms ( I understand) The flight attendant allowed the teenager sitting in my row to move to be with friend? Would have loved the same from my husband at back of plane! Why did attendant ask me twice to push my bag under the seat and NEVER once said anything to man in aisle across from me?? His was laying in floor!! Rate food? What food? Just drinks were offered for a price. Should be against the law to charge $5 for water. No… not the best flight.

The bag situation was confusing. I didn’t know I had to pay for Carry ons. The seats were uncomfortable and there was no entertainment

Spirit Airlines at Laguardia is a small terminal so it is quick to get to your gate and to get your luggage. The flight is short enough to orlando and the price was very inexpensive. The seats do not move so you can't recline. Drinks and snakcks should be complimentary.

Bad. I know TSA is a mess right now but they “overbooked” the flight and almost didn’t let 10 of us on. Can’t put even a normal backpack under the seat, tray table is barely a foot wide, have to pay for literally everything. Apparently you can bid on your seats, too, so really the baseline ticket only covers the possibility of maybe getting on the plane. The staff were nice though, can only imagine the stress they are under.

I was double booked for my ticket- they have record of it and admitted to their error but wouldn’t let me board until I paid once again for the fare- have documentation of their mistake -

The flight time did not match my original email on time of flight. Missed the first flight. The representative I got on the phone was so incompetent it was unbelievable. My guess is it was AI but it told me it was not AI. They did get me rebooked which I was very thankful of. The return flight was delayed because of staffing issues for the plane and when we reached our destination the jet bridge would not work so we sat on the plane another 40 minutes. I did get to my destination and I did get home but not a good experience.

My flight was cancelled I missed time at work and got a parking ticket

It was terrible. I had to pay again once I got to the airport because they said they never received the payment.

Customer service online / on the phone are horrible. Flight crew is great but gate agents and customer service are terrible

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.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

First of all we hade waited 3 hours in the airplane waiting to leave. Second the return schedule was changed and it messed up my entire vaction. I won't buy never again another flight and recommend to nobody traveling with them.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

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.