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$101+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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Find 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 October 27, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/18:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Sat 12/67:07 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 10/25$207
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Sat 11/1511:35 amORD - SJU
1 stop13h 58mMultiple Airlines
Fri 11/217:10 amSJU - ORD
1 stop12h 49mMultiple Airlines
Deal found 10/27$212
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Sun 11/1612:17 pmORD - SJU
1 stop11h 15mMultiple Airlines
Sun 11/234:12 pmSJU - ORD
Nonstop5h 11mMultiple Airlines
Deal found 10/25$214
This Cheapflightsfares deal was found by Cheapflights users on 10/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/218:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Thu 12/49:47 pmSJU - ORD
Nonstop5h 12mSpirit Airlines
Deal found 10/25$217
This CheapOair deal was found by Cheapflights users on 10/27. 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.
Sun 12/75:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Fri 12/128:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 10/27$218
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/176:40 amORD - SJU
2 stops30h 02mMultiple Airlines
Fri 11/215:19 pmSJU - ORD
1 stop17h 58mMultiple Airlines
Deal found 10/27$220
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Sun 12/77:10 amORD - SJU
1 stop12h 55mAmerican Airlines
Fri 12/123:58 pmSJU - ORD
Nonstop5h 31mAmerican Airlines
Deal found 10/27$223
This Frontier deal was found by Cheapflights users on 10/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:11 amORD - SJU
1 stop7h 10mFrontier
Fri 12/123:06 pmSJU - ORD
1 stop7h 36mFrontier
Deal found 10/25$225
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/126:40 amORD - SJU
1 stop9h 14mMultiple Airlines
Thu 11/209:30 pmSJU - ORD
1 stop15h 05mMultiple Airlines
Deal found 10/27$227
This Frontier deal was found by Cheapflights users on 10/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/38:36 amORD - SJU
1 stop7h 47mFrontier
Thu 12/114:31 pmSJU - ORD
1 stop7h 53mFrontier
Deal found 10/25$230
This United Airlines deal was found by Cheapflights users on 10/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/169:30 amORD - STT
Nonstop4h 48mUnited Airlines
Sun 11/233:05 pmSTT - ORD
Nonstop5h 40mUnited Airlines
Deal found 10/25$242
This American Airlines deal was found by Cheapflights users on 10/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/158:05 amORD - STT
Nonstop4h 43mAmerican Airlines
Thu 11/206:17 pmSTT - ORD
1 stop8h 20mAmerican Airlines
Deal found 10/25$247

Cheap 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 October 27, 2025.

Round-trip from

$207
(Cheapflightsfares)

One-way from

$101
(Expedia)

Popular in

December

Cheapest in

April

Average price

$360

Good round-trip deal

$350 or less

Good one-way deal

$191 or less
From Chicago O'Hare Intl to Caribbean
Search Deals
One-way flight from Chicago O'Hare Intl to Caribbean
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Highest demand for flights based on searches. 7% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Caribbean.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Caribbean.
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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 October 27, 2025.
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

Tue 2/3

1:00 pm-12:36 am

1 stop9h 36m

San Juan Luis Munoz Marin Intl

Tue 2/10

5:50 pm-11:39 pm

1 stop7h 49m

$227

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Mon 2/16

9:30 am-4:18 pm

Nonstop4h 48m

Saint Thomas Island Cyril E King

Thu 2/19

3:05 pm-6:45 pm

Nonstop5h 40m

$242

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 12/13

8:05 am-2:52 pm

Nonstop4h 47m

Saint Thomas Island Cyril E King

Thu 12/18

1:30 pm-12:43 am

1 stop13h 13m

$247

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

8:55 am-3:40 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Thu 1/22

2:05 am-9:40 am

1 stop9h 35m

$261

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/28

6:20 pm-6:11 am

1 stop9h 51m

San Juan Luis Munoz Marin Intl

Tue 3/3

8:35 am-11:57 am

Nonstop5h 22m

$288

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 11/16

7:52 am-2:22 pm

Nonstop4h 30m

Punta Cana

Thu 11/20

2:55 pm-6:08 pm

Nonstop5h 13m

$306

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 12/24

6:45 am-4:23 pm

1 stop7h 38m

San Juan Luis Munoz Marin Intl

Fri 1/2

2:21 pm-10:04 pm

1 stop9h 43m

$308

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 3/25

12:10 pm-10:00 pm

1 stop8h 50m

San Juan Luis Munoz Marin Intl

Mon 3/30

1:59 am-12:50 pm

1 stop11h 51m

$308

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 4/8

1:45 pm-10:47 pm

1 stop8h 02m

San Juan Luis Munoz Marin Intl

Tue 4/21

1:59 am-12:50 pm

1 stop11h 51m

$308

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Thu 12/11

6:00 am-5:25 pm

1 stop9h 25m

Punta Cana

Fri 12/19

2:55 pm-6:08 pm

Nonstop5h 13m

$311

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 60 results
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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, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $127). Flying from Chicago O'Hare Intl Airport to Caribbean in December is currently the most expensive (average of $188). 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 October 27, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Caribbean at noon. If you’re flexible enough to do this you can expect to save up to 24% 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 October 26, 2025.

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

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 October 27, 2025.

The most flights from ORD to 0CB are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 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 October 27, 2025.
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
7,996 reviews

Comfort

7.9

Overall

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,996 reviews
Delta
7.9
Good
7,996 reviews

Comfort

7.9

Overall

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,999 reviews
Delta
7.9
Good
7,996 reviews

Comfort

7.9

Overall

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,031 reviews
Delta
7.9
Good
7,996 reviews

Comfort

7.9

Overall

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Spirit Airlines
6.3
Okay
8,112 reviews
Delta
7.9
Good
7,996 reviews

Comfort

7.9

Overall

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Frontier
5.8
Fair
3,123 reviews
Delta
7.9
Good
7,996 reviews

Comfort

7.9

Overall

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 $247, United Airlines can have you in Caribbean from Chicago O'Hare Intl Airport in 4h 47m. The distance between Chicago O'Hare Intl Airport and Caribbean is about 2116 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 Spirit Airlines. According to our data, you can fly for as low as $101. Users have also found prices from $109 and $123 on United Airlines and Southwest, 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 - Montego Bay Sangster Intl 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: American Airlines (91%), Alaska Airlines (82%), Spirit Airlines (78%).

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

    On average you can expect to pay $822 for a flight from Chicago O'Hare Intl Airport to Caribbean. The cheapest flight overall is $109 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $197.

  • 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, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $127). Flying from Chicago O'Hare Intl Airport to Caribbean in December is currently the most expensive (average of $188). 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.

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Alternative routes for O'Hare Intl to Caribbean

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

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 October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$508FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$402FlexibilityNo cancel feeOn-time65%
DeltaCheapest$186Average$606FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$226Average$637FlexibilityNo cancel feeOn-time69%
ArajetCheapest$233Average$331FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$261Average$470FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$345Average$636FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$385Average$478FlexibilityNo cancel feeOn-time63%

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