$87 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 3/24. 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 Cana1 stop$288
Santo Domingo
Santo Domingo1 stop$295
Montego Bay
Montego Bay1 stop$297
Oranjestad
Oranjestad1 stop$366
Nassau
Nassau1 stop$469
Kingston
Kingston1 stop$352
Simpson Bay
Simpson Bay1 stop$293
Providenciales
Providenciales1 stop$371
George Town
George Town1 stop$458
St. John's
St. John's1 stop$466
Aguadilla
Aguadilla1 stop$202
Punta Cana
Punta Cana1 stop$288
Santo Domingo
Santo Domingo1 stop$295
Montego Bay
Montego Bay1 stop$297
Oranjestad
Oranjestad1 stop$366
Nassau
Nassau1 stop$469
Kingston
Kingston1 stop$352
Simpson Bay
Simpson Bay1 stop$293
Providenciales
Providenciales1 stop$371
George Town
George Town1 stop$458
St. John's
St. John's1 stop$466
Aguadilla
Aguadilla1 stop$202

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

Thu, May 14 - Thu, May 21
Frontier Logo
5:16 pm - 12:53 am
ORD
-
SJU
6h 37m
1 stop
Frontier Logo
8:10 pm - 12:25 am
SJU
-
ORD
5h 15mnonstop
$184Frontier
Sat, May 16 - Fri, May 22
Frontier Logo
8:00 am - 3:37 pm
ORD
-
SJU
6h 37m
1 stop
Frontier Logo
8:10 pm - 12:25 am
SJU
-
ORD
5h 15mnonstop
$186Frontier
Tue, Mar 10 - Thu, Mar 12
Spirit Airlines Logo
12:22 pm - 5:54 pm
ORD
-
SJU
4h 32mnonstop
Spirit Airlines Logo
1:29 am - 5:45 am
SJU
-
ORD
5h 16mnonstop
$198Spirit Airlines
Wed, Apr 8 - Wed, Apr 15
Spirit Airlines Logo
4:36 pm - 1:26 pm
ORD
-
STT
19h 50m
2 stops
Spirit Airlines Logo
1:23 pm - 11:10 pm
STT
-
ORD
10h 47m
1 stop
$261Spirit Airlines
Mon, Mar 2 - Sat, Mar 7
Arajet Logo
5:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
$292Arajet
Mon, Mar 2 - Sat, Mar 7
Arajet Logo
5:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
$296Arajet
Sun, Apr 12 - Sun, Apr 19
American Airlines Logo
6:05 am - 1:25 pm
ORD
-
MBJ
7h 20m
1 stop
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
$297American Airlines
Wed, Mar 11 - Wed, Mar 18
United Airlines Logo
8:42 am - 12:46 pm
ORD
-
MBJ
4h 04mnonstop
United Airlines Logo
1:48 pm - 6:13 pm
MBJ
-
ORD
4h 25mnonstop
$298United Airlines
Sat, May 9 - Fri, May 15
American Airlines Logo
8:46 pm - 1:25 pm
ORD
-
MBJ
16h 39m
1 stop
American Airlines Logo
2:29 pm - 10:44 am
MBJ
-
ORD
20h 15m
1 stop
$299American Airlines
Fri, May 8 - Fri, May 15
United Airlines Logo
8:45 am - 3:10 pm
ORD
-
MBJ
6h 25m
1 stop
United Airlines Logo
2:40 pm - 7:54 am
MBJ
-
ORD
17h 14m
1 stop
$302United 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 $171 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 $171.

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 April, when tickets cost $339 (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$87
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Chicago O'Hare Airport to Oranjestad

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 8238 reviews
7.8Entertainment
7.2Food
8.5Crew
8.1Boarding
7.9Comfort
Airline reviews

2+hrs delay without any reason provided and a cramped flight

2.0 MediocreYogendra Kumar, Feb 2026
DTW - MDT
Read more Delta reviews

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

Never got on it. Was re-routed through Detroit and am still in airports 12 hours later waiting for my connecting plane to arrive.

Delta has too many delays now days. It is 1:06 am now. I was supposed to land in Norfolk at 10:30 pm. I got re-booked through Detroit and I’m still in Detroit. I hope to be landed in Norfolk by 3am. I’ve been in airports for 12 hours as of right now. There is a weather delay now but most delays lately have been maintenance.

Very Very late. Subsequent flights left an hour before ours

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. :/

Not United Airlines' fault. It's ORL airport's fault.

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.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

It was cancelled a few hours before take off. Spirit has yet to confirm I will be refunded for the trip

gate agents with the different rules at the different airports. made me pay for my bag as a carry on instead of a personal item, yet it fit under the seat on the way from Indy to Ft Laud

charging $3 for really bad and cold coffee on airplane flight is ridiculous.

We flew Spirit because it was cheaper but the seats were so uncomfortable. I don;t need to be fed snacks on a plane but when it's a 3-4 hour trip then at least a drink is nice. The flight attendants had nothing to do the whole flight except for gossip loudly to each other right behind our seats, and they talked so much my husband couldn't even rest! I was fine with no tv or entertainment but the seats were so uncomfortable with no recline, no padding, and I am short but even for me to leg room was tough for a 3-4 hour trip. We probably would fly spirit again if we had to, but it's definitely not our favorite!

There was absolutely nothing good about this fight. They delayed us for over 2 hours to give our plane to a flight going to Tampa. By the time we got to norfolk conditions were too bad to land so they took us to Charlotte to refuel so they could fly back to Fort lauderdale. There was almost no communication from the pilot, no wifi, no chargers, and they wouldn't even give us free water when we were stuck in Charlotte refueling.

Checking in and getting to gate fast and leasy at Laguardia airport. There is no entertainment on the plane and food was for purchase. Great experience flying with spirit

The flight itself and the crew were great. Sitting on the tarmac for over an hour until our gate opened up was really frustrating. Missed our scheduled bus and got home two hours later

This flight cancelled. I am in the airport right now and my kids sleep on the floor. We are waiting for information in the line 4 hours and rude woman from spirit airline offers us flight to Austin on 23 February. No water no food offer. The offer to book hotel and they will refund 150$. The nearest hotel 450$ per night. So I got flight to San Antonio 02/22 at 7am. I hate this company, they are rude and no empathy. So many people with kids were there. And I don’t sleep and it is cold here. I don’t have warm clothes for me and my kids. And I don’t have money for transport from San Antonio to my Austin.

It was the most turbulent terrifying flight I’ve ever been on. I will never fly spirit again.

We sat on the tarmac for an hour and a half after landing.

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.