HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$66+ Cheap flights from O'Hare Intl (ORD) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'Hare Intl to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from O'Hare Intl to Caribbean

Cheapest flights from O'Hare Intl to Caribbean
Explore the most affordable flight options available from O'Hare Intl to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

This CheapOair deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/212:17 pm
ORD
-
SJU
Nonstop4h 32m
Multiple Airlines
Mon 2/93:53 am
SJU
-
ORD
1 stop13h 59m
Multiple Airlines
Deal found 1/24$185
This CheapOair deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/167:26 pm
ORD
-
SJU
Nonstop4h 33m
Spirit Airlines
Wed 3/2511:07 am
SJU
-
ORD
1 stop8h 28m
Spirit Airlines
Deal found 1/26$186
This Booking.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/212:17 pm
ORD
-
SJU
Nonstop4h 32m
Multiple Airlines
Wed 2/115:25 pm
SJU
-
ORD
1 stop19h 21m
Multiple Airlines
Deal found 1/26$187
This Kiwi.com deal was found by Cheapflights users on 1/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:17 pm
ORD
-
SJU
Nonstop4h 32m
Multiple Airlines
Tue 3/33:53 am
SJU
-
ORD
1 stop13h 59m
Multiple Airlines
Deal found 1/23$188
This Kiwi.com deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/178:30 am
ORD
-
SJU
1 stop16h 18m
Frontier
Tue 2/245:25 pm
SJU
-
ORD
1 stop24h 27m
Frontier
Deal found 1/25$189
This Kiwi.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Thu 4/91:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/26$190
This Priceline deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2512:22 pm
ORD
-
SJU
Nonstop4h 32m
Multiple Airlines
Sat 5/28:00 am
SJU
-
ORD
1 stop8h 25m
Multiple Airlines
Deal found 1/24$191
This Kiwi.com deal was found by Cheapflights users on 1/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:01 pm
ORD
-
SJU
1 stop9h 52m
Multiple Airlines
Tue 3/312:32 pm
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Deal found 1/23$192
This CheapOair deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:15 am
ORD
-
SJU
1 stop16h 38m
Frontier
Tue 2/243:53 am
SJU
-
ORD
1 stop13h 59m
Frontier
Deal found 1/24$193
This Kiwi.com deal was found by Cheapflights users on 1/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/188:30 am
ORD
-
SJU
1 stop14h 13m
Multiple Airlines
Fri 2/275:45 pm
SJU
-
ORD
1 stop8h 55m
Multiple Airlines
Deal found 1/23$194
This CheapOair deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1812:20 pm
ORD
-
SJU
1 stop9h 31m
Multiple Airlines
Mon 3/231:29 am
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Deal found 1/25$195
This CheapOair deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2112:17 pm
ORD
-
SJU
Nonstop4h 32m
Multiple Airlines
Tue 2/243:53 am
SJU
-
ORD
1 stop13h 59m
Multiple Airlines
Deal found 1/26$196

Find flight deals from O'Hare Intl to Caribbean

Keep the following information in mind while searching for O'Hare Intl to Caribbean flight deals. Data was last updated January 26, 2026.

Round-trip from

$185
(JetBlue)

One-way from

$66
(Expedia)

Popular in

December

Cheapest in

April

Average price

$358

Good round-trip deal

$303 or less

Good one-way deal

$128 or less
From Chicago O'Hare Intl to Caribbean
Search Deals
One-way flight from Chicago O'Hare Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Caribbean.
Search Deals
Price to beat on a one-way flight from Chicago O'Hare Intl to Caribbean.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 26, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Caribbean that are best for you.

Fly from

O'Hare Intl

Fly to

Caribbean

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 2/26

12:44 pm-12:29 am

1 stop9h 45m

San Juan Luis Munoz Marin Intl

Wed 3/11

3:26 am-11:25 am

1 stop8h 59m

$192

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 3/13

5:00 pm-1:42 am

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Tue 3/24

3:26 am-11:25 am

1 stop8h 59m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 3/13

5:00 pm-1:42 am

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Mon 3/23

3:26 am-11:25 am

1 stop8h 59m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/28

12:59 pm-10:31 pm

1 stop7h 32m

San Juan Luis Munoz Marin Intl

Wed 3/4

5:01 am-12:04 pm

1 stop9h 03m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 3/3

10:00 am-9:56 pm

1 stop9h 56m

San Juan Luis Munoz Marin Intl

Mon 3/9

4:15 am-11:48 am

1 stop8h 33m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/28

12:59 pm-12:29 am

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Thu 3/5

3:05 pm-10:59 pm

1 stop9h 54m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

6:04 am-4:56 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

Wed 2/25

1:44 pm-10:59 pm

1 stop11h 15m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/28

12:59 pm-12:29 am

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Tue 3/3

5:01 am-11:49 am

1 stop8h 48m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

6:04 am-4:56 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

Thu 2/26

5:10 am-11:54 am

1 stop8h 44m

$206

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/28

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Sat 3/7

3:20 pm-11:47 pm

1 stop10h 27m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from O'Hare Intl to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Caribbean

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $126). Flying from Chicago O'Hare Intl Airport to Caribbean in December is currently the most expensive (average of $195). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to CB?

Find hourly flight availability from O'Hare Intl to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 26, 2026.

A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Caribbean in the evening. If you’re flexible enough to do this you can expect to save up to 39% on your trip compared to booking a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Caribbean. Price data was last updated on January 24, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Caribbean flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago O'Hare Intl Airport to Caribbean

Explore weekly flight availability from O'Hare Intl to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 26, 2026.

The most flights from ORD to 0CB are scheduled on a Monday (11 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 on average).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated January 26, 2026.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Chicago O'Hare Intl Airport to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,111 reviews

Comfort

7.9

Boarding

8.1

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,111 reviews
Delta
7.9
Good
8,111 reviews

Comfort

7.9

Boarding

8.1

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,199 reviews
Delta
7.9
Good
8,111 reviews

Comfort

7.9

Boarding

8.1

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,189 reviews
Delta
7.9
Good
8,111 reviews

Comfort

7.9

Boarding

8.1

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,379 reviews
Delta
7.9
Good
8,111 reviews

Comfort

7.9

Boarding

8.1

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.7
Fair
3,058 reviews
Delta
7.9
Good
8,111 reviews

Comfort

7.9

Boarding

8.1

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago O'Hare Intl Airport to Caribbean?

    For as low as $356, JetBlue can have you in Caribbean from Chicago O'Hare Intl Airport in 4h 45m. The distance between Chicago O'Hare Intl Airport and Caribbean is about 1982 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Caribbean one-way?

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $82. Users have also found prices from $83 and $87 on Frontier and Spirit Airlines, respectively.

  • What are the most popular routes from Chicago O'Hare Intl Airport to Caribbean?

    Most travelers choose Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago O'Hare Intl - Punta Cana or Chicago O'Hare Intl - Saint Thomas Island Cyril E King when deciding on the best route from Chicago O'Hare Intl Airport to Caribbean.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Caribbean?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago O'Hare Intl Airport to Caribbean on time: United Airlines (81%), Air New Zealand (81%), Air Canada (80%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Caribbean?

    On average you can expect to pay $527 for a flight from Chicago O'Hare Intl Airport to Caribbean. The cheapest flight overall is $89 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $99.

  • Can I find deals for flights from O'Hare Intl to Caribbean that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Caribbean.

  • Can I find deals for business class flights from O'Hare Intl to Caribbean?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $126). Flying from Chicago O'Hare Intl Airport to Caribbean in December is currently the most expensive (average of $195). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for O'Hare Intl to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Miami flights
O'Hare Intl to Orlando flights
O'Hare Intl to Denver flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Seattle flights
O'Hare Intl to Tampa flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Newark flights
Midway to Fort Lauderdale flights
O'Hare Intl to Narita flights
Midway to Sky Harbor Intl flights
Midway to Cancún flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Heathrow flights
O'Hare Intl to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to West Palm Beach flights
Midway to Miami flights
O'Hare Intl to Cozumel flights
O'Hare Intl to Charles de Gaulle flights
Midway to Dallas/Fort Worth flights
Midway to Las Vegas flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Haneda flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to San Diego flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Boston flights
O'Hare Intl to Reagan-National flights
Midway to Orlando flights
O'Hare Intl to Ontario flights
Midway to Newark flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Dublin flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Charleston flights
Midway to Mexico City flights
O'Hare Intl to Hobby flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Baltimore flights

Top 9 airlines flying from O'Hare Intl to Caribbean

Discover the top 9 airlines that operate flights from O'Hare Intl to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$505FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$120Average$447FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$130Average$372FlexibilityNo cancel feeOn-time65%
DeltaCheapest$136Average$538FlexibilityNo cancel feeOn-timeN/A
ArajetCheapest$181Average$322FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$193Average$590FlexibilityNo cancel feeOn-time67%
Hahn AirCheapest$213Average$343FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$604FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.