$71 Find Cheap Flights from Chicago O'Hare Airport to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Caribbean departing on 2/26. 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

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Cheap Flights from O'Hare Intl to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cananonstop$250
Santo Domingo
Santo Domingo1 stop$277
Montego Bay
Montego Baynonstop$377
Oranjestad
Oranjestad1 stop$344
Nassau
Nassau1 stop$353
Kingston
Kingston1 stop$333
Simpson Bay
Simpson Bay1 stop$214
Providenciales
Providenciales1 stop$443
Port of Spain
Port of Spain2 stops$430
Bridgetown
Bridgetown1 stop$390
George Town
George Town2 stops$324
Willemstad
Willemstad2 stops$365
Castries
Castries2 stops$781
St. John's
St. John's1 stop$443
Puerto Plata
Puerto Plata1 stop$388
Aguadilla
Aguadilla1 stop$181
Punta Cana
Punta Cananonstop$250
Santo Domingo
Santo Domingo1 stop$277
Montego Bay
Montego Baynonstop$377
Oranjestad
Oranjestad1 stop$344
Nassau
Nassau1 stop$353
Kingston
Kingston1 stop$333
Simpson Bay
Simpson Bay1 stop$214
Providenciales
Providenciales1 stop$443
Port of Spain
Port of Spain2 stops$430
Bridgetown
Bridgetown1 stop$390
George Town
George Town2 stops$324
Willemstad
Willemstad2 stops$365
Castries
Castries2 stops$781
St. John's
St. John's1 stop$443
Puerto Plata
Puerto Plata1 stop$388
Aguadilla
Aguadilla1 stop$181

Book Cheap O'Hare Intl to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Caribbean 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 O'Hare Intl to Caribbean

Sun, Jan 11 - Sat, Jan 17
Multiple Airlines Logo
4:38 pm - 3:13 am
ORD
-
SJU
8h 35m1 stop
Multiple Airlines Logo
8:00 am - 5:52 pm
SJU
-
ORD
11h 52m2 stops
$194Multiple Airlines
Mon, Jan 19 - Sat, Jan 31
Frontier Logo
6:20 am - 3:27 pm
ORD
-
SJU
7h 07m1 stop
Frontier Logo
11:49 am - 10:44 pm
SJU
-
ORD
12h 55m1 stop
$195Frontier
Sat, Feb 21 - Wed, Feb 25
JetBlue Logo
6:04 am - 4:56 pm
ORD
-
SJU
8h 52m1 stop
JetBlue Logo
5:10 am - 11:48 am
SJU
-
ORD
8h 38m1 stop
$196JetBlue
Sun, Jan 25 - Wed, Feb 4
Spirit Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Spirit Airlines Logo
1:22 pm - 4:37 pm
SJU
-
ORD
5h 15mnonstop
$197Spirit Airlines
Wed, Jan 28 - Thu, Feb 5
Spirit Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Spirit Airlines Logo
1:22 pm - 4:37 pm
SJU
-
ORD
5h 15mnonstop
$199Spirit Airlines
Sat, Feb 7 - Sat, Feb 14
Arajet Logo
10:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
$250Arajet
Sat, Feb 7 - Sat, Feb 14
Arajet Logo
10:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
$255Arajet
Mon, Jan 12 - Thu, Jan 15
American Airlines Logo
10:09 am - 3:22 pm
ORD
-
MBJ
4h 13mnonstop
American Airlines Logo
3:12 pm - 6:51 pm
MBJ
-
ORD
4h 39mnonstop
$377American Airlines
Sat, Jan 24 - Thu, Jan 29
American Airlines Logo
5:26 pm - 12:24 pm
ORD
-
MBJ
17h 58m1 stop
American Airlines Logo
3:12 pm - 6:51 pm
MBJ
-
ORD
4h 39mnonstop
$381American Airlines
Thu, Feb 5 - Thu, Feb 12
JetBlue Logo
9:40 am - 2:06 pm
ORD
-
PLS
27h 26m1 stop
JetBlue Logo
3:12 pm - 11:10 pm
PLS
-
ORD
8h 58m1 stop
$444JetBlue
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Caribbean flights

Get data-powered insights and trends into flights from O'Hare Intl to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago O'Hare Intl Airport to Caribbean flight route?

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

The cheapest ticket to Caribbean from Chicago O'Hare Intl Airport found in the last 72 hours was to San Juan, at $189 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 $189.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Caribbean?

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 $592, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Caribbean, 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 O'Hare Intl Airport to Caribbean is April, when tickets cost $338 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $529 and $450 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Caribbean?

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

If you are looking for a flight deal from Chicago O'Hare Airport to Caribbean, look for departures on Mondays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Caribbean, Friday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Caribbean, 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 O'Hare Intl Airport to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$71
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 24% increase in price.
Flight from Chicago O'Hare Airport to Simpson Bay

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Caribbean?

    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 O'Hare Airport to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport to Caribbean 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 O'Hare Airport to Caribbean?

    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 O'Hare Airport to Caribbean 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 O'Hare Airport to Caribbean?

    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 O'Hare Airport to Caribbean 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?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $322 on average. Morning departures are around 12% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $443.

Reviews of the top 5 airlines serving from O'Hare Intl to Caribbean

 
Need help choosing which airline to fly with from O'Hare Intl to Caribbean? 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 8014 reviews
7.3Food
8.5Crew
7.9Entertainment
8.1Boarding
7.9Comfort
Airline reviews

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

2.0 MediocrePeter, Dec 2025
JFK - MEM
Read more Delta reviews

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Great. I had to modify a flight. That was easy and free. Thank You

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

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.

Spirit cancelled the flight very late last night, I was on the way to the airport when I found out

First time in a decade I threw up on the flight, turbulence was terrible!! The staff were kinda rude at times.

Boarding was good, clearly explained and efficient. Staff were helpful, I would've liked a place to get coffee that wasn't Starbucks

The most horrible flight ever not only Spirit delayed our flight 2 hours departure time for a 1 hour flight — that I could have driven FLL to TPA and spend less time on the road —- and they did the same on the return with 2-hr delay again!!! Then to top all, the rubber like and most unconfortable seats in the industry with no leg room!!! There should be an award for these kinds of companies measuring % of returning customers!!!

The flight was cancelled and Spirit said they could not rebook me on another flight for six days. They said they couldn't do anything for another six days.

Flight was on time, Newark staff, especially Nathan, very helpful, and plane crew to RDU very good without being pushy. We arrived early, and had a gentle landing.

See my last comment for the first leg. That should’ve been in here

Horrible. Arrived at my gate at 6:37 for a 6:50 flight and was denied by staff to board. Literally watched my flight leave from the window and it didn’t take off until after 7am. Tried to talk to staff and they were rude beyond compare. Will never fly with this airline again.

Our flight got rescheduled 48 hours later, the airline didn’t pay a penny for our expenses.

We had to sit and wait for almost an hour after landing and taxiing to the gate. The jet bridge was broken so we just waited and waited and waited and it was inconvenient, hot, and unnecessary.

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports