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Caribbean Islands

$70+ Cheap flights from O'Hare Intl (ORD) to Caribbean Islands

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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Caribbean Islands

Cheapest flights from O'Hare Intl to Caribbean Islands
Explore the most affordable flight options available from O'Hare Intl to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 21, 2025.

This Trip.com deal was found by Cheapflights users on 12/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:15 pmORD - SJU
1 stop8h 14mFrontier
Thu 1/86:30 amSJU - ORD
1 stop10h 58mFrontier
Deal found 12/21$198
This CheapOair deal was found by Cheapflights users on 12/20. 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 12/312:15 pmORD - SJU
1 stop8h 14mFrontier
Wed 1/73:08 pmSJU - ORD
1 stop26h 20mFrontier
Deal found 12/20$214
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 12/312:15 pmORD - SJU
1 stop8h 14mMultiple Airlines
Fri 1/97:10 amSJU - ORD
1 stop17h 32mMultiple Airlines
Deal found 12/20$218
This Frontier deal was found by Cheapflights users on 12/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:15 pmORD - SJU
1 stop8h 14mFrontier
Fri 1/97:10 amSJU - ORD
1 stop11h 57mFrontier
Deal found 12/21$227
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:25 pmORD - SJU
Nonstop4h 35mAmerican Airlines
Thu 1/156:00 amSJU - ORD
Nonstop5h 35mAmerican Airlines
Deal found 12/21$236
This eDestinos deal was found by Cheapflights users on 12/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:30 pmORD - SJU
1 stop13h 04mFrontier
Thu 1/86:30 amSJU - ORD
1 stop10h 58mFrontier
Deal found 12/20$291
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 12/3112:39 pmORD - SJU
1 stop9h 15mMultiple Airlines
Thu 1/86:00 amSJU - ORD
2 stops11h 12mMultiple Airlines
Deal found 12/20$297
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/315:45 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Fri 1/96:49 pmPUJ - ORD
2 stops50h 28mMultiple Airlines
Deal found 12/19$325
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Mon 12/295:45 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Wed 12/311:28 pmPUJ - ORD
1 stop8h 38mMultiple Airlines
Deal found 12/20$328
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Mon 12/295:45 amORD - PUJ
Nonstop4h 45mArajet
Tue 12/307:30 pmPUJ - ORD
Nonstop5h 10mArajet
Deal found 12/20$331
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Mon 12/295:45 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Tue 12/307:00 amPUJ - ORD
2 stops37h 33mMultiple Airlines
Deal found 12/20$339
This Frontier deal was found by Cheapflights users on 12/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:10 amORD - PUJ
Nonstop4h 37mFrontier
Wed 12/311:28 pmPUJ - ORD
1 stop8h 38mFrontier
Deal found 12/21$347

Find flight deals from O'Hare Intl to Caribbean Islands

Keep the following information in mind while searching for O'Hare Intl to Caribbean Islands flight deals. Data was last updated December 21, 2025.

Round-trip from

$195
(eDestinos)

One-way from

$70
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$565
From Chicago O'Hare Intl to Caribbean Islands
Search Deals
One-way flight from Chicago O'Hare Intl to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Caribbean Islands 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 December 21, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Caribbean Islands that are best for you.

Fly from

O'Hare Intl

Fly to

Caribbean Islands

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/7

8:45 am-7:13 pm

1 stop8h 28m

San Juan Luis Munoz Marin Intl

Sat 2/14

5:22 pm-11:10 pm

1 stop7h 48m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 1/29

9:40 am-7:26 pm

1 stop7h 46m

San Juan Luis Munoz Marin Intl

Mon 2/2

11:06 am-7:36 pm

1 stop10h 30m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 2/25

12:41 pm-10:25 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

Sun 3/1

5:10 am-11:48 am

1 stop8h 38m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/28

9:40 am-7:23 pm

1 stop7h 43m

San Juan Luis Munoz Marin Intl

Mon 2/2

11:06 am-7:36 pm

1 stop10h 30m

$211

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/6

7:45 am-6:02 pm

1 stop8h 17m

San Juan Luis Munoz Marin Intl

Sat 2/14

5:22 pm-11:10 pm

1 stop7h 48m

$211

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 2/10

8:45 am-7:13 pm

1 stop8h 28m

San Juan Luis Munoz Marin Intl

Fri 2/27

5:10 am-11:48 am

1 stop8h 38m

$214

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

10:15 am-7:26 pm

1 stop7h 11m

San Juan Luis Munoz Marin Intl

Fri 1/23

11:06 am-7:36 pm

1 stop10h 30m

$214

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/11

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 1/16

4:52 pm-8:20 pm

Nonstop5h 28m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/17

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Mon 1/26

11:06 am-7:36 pm

1 stop10h 30m

$216

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/25

8:43 pm-2:10 pm

1 stop15h 27m

Simpson Bay Princess Juliana

Fri 1/30

3:15 pm-11:46 pm

1 stop10h 31m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

Showing 1-10 of 60 results
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Best time to book a flight from O'Hare Intl to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean Islands (average of $127). Flying from Chicago O'Hare Intl Airport to Caribbean Islands in December is currently the most expensive (average of $220). 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 EPX?

Find hourly flight availability from O'Hare Intl to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 21, 2025.

One of the essential ways to save on airfare from Chicago O'Hare Intl Airport to Caribbean Islands is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 29% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Caribbean Islands. Price data was last updated on December 20, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Caribbean Islands flight should consider departing on Friday evenings when fares are most often at their lowest. Thursday mornings 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 Islands

Explore weekly flight availability from O'Hare Intl to Caribbean Islands. 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 December 21, 2025.

The most flights from ORD to zzEPX are scheduled on a Monday (12 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated December 21, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Chicago O'Hare Intl Airport to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

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
8,014 reviews
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

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
9,102 reviews
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

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
11,052 reviews
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

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
8,193 reviews
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

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
5.8
Fair
3,077 reviews
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

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 Islands. 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 Islands?

    For as low as $351, JetBlue can have you in Caribbean Islands from Chicago O'Hare Intl Airport in 4h 45m. The distance between Chicago O'Hare Intl Airport and Caribbean Islands is about 1982 mi. This flight may include one or multiple stops.

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

    The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Caribbean Islands are JetBlue ($82), Frontier ($83), and Spirit Airlines ($92).

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

    Most travelers choose Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago O'Hare Intl - Punta Cana or Chicago O'Hare Intl - Oranjestad Reina Beatrix when deciding on the best route from Chicago O'Hare Intl Airport to Caribbean Islands.

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

    The top 3 most reliable airlines when flying from Chicago O'Hare Intl Airport to Caribbean Islands are Air Canada (80%), United Airlines (80%) and Air New Zealand (80%).

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

    Looking at all options, your cheapest flight can be booked for $100. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $141 on average, our data indicates $690 when flying from Chicago O'Hare Intl Airport to Caribbean Islands.

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

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

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

    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 Islands.

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

    Yes. Cheapflights offers flight deals from O'Hare Intl to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean Islands (average of $127). Flying from Chicago O'Hare Intl Airport to Caribbean Islands in December is currently the most expensive (average of $220). 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

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Alternative routes for O'Hare Intl to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from O'Hare Intl to Caribbean Islands

Discover the top 9 airlines that operate flights from O'Hare Intl to Caribbean Islands. 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 December 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$112Average$507FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$144Average$450FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$146Average$375FlexibilityNo cancel feeOn-time65%
DeltaCheapest$186Average$573FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$215Average$614FlexibilityNo cancel feeOn-time69%
ArajetCheapest$236Average$338FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$277Average$568FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$343Average$622FlexibilityNo cancel feeOn-time71%

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