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$93+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$209
(Cheapflightsfares)

One-way from

$93
(Expedia)

Popular in

December

Cheapest in

October

Average price

$317

Good round-trip deal

$346 or less

Good one-way deal

$178 or less
From Chicago O'Hare Intl to Caribbean
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One-way flight from Chicago O'Hare Intl to Caribbean
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Highest demand for flights based on searches. 10% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in September 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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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 September 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Sat 10/183:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Sat 10/255:18 pmSJU - ORD
1 stop19h 15mSpirit Airlines
Deal found 9/11$208
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Tue 9/236:30 amORD - SJU
1 stop6h 41mSpirit Airlines
Tue 9/306:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 9/11$209
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Sat 10/117:43 pmORD - STT
1 stop13h 13mSpirit Airlines
Wed 10/1511:01 amSTT - ORD
1 stop8h 37mSpirit Airlines
Deal found 9/10$211
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Thu 9/256:44 pmORD - SJU
1 stop15h 20mSpirit Airlines
Thu 10/27:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
Deal found 9/10$211
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 10/35:17 pmORD - SJU
1 stop6h 37mSpirit Airlines
Wed 10/83:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/10$212
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
Tue 10/76:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Wed 10/83:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/9$213
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Sat 10/186:58 pmORD - STT
1 stop17h 01mSpirit Airlines
Sat 10/2511:01 amSTT - ORD
1 stop13h 44mSpirit Airlines
Deal found 9/10$214
This Frontier deal was found by Cheapflights users on 9/9. 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.
Sat 10/256:40 amORD - SJU
1 stop7h 44mFrontier
Fri 10/315:51 pmSJU - ORD
2 stops18h 39mFrontier
Deal found 9/9$214
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 10/35:17 pmORD - SJU
1 stop6h 37mSpirit Airlines
Tue 10/73:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/10$215
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Sat 12/610:15 amORD - SJU
1 stop8h 29mSpirit Airlines
Wed 12/172:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 9/10$216
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Sat 10/117:43 pmORD - SJU
1 stop14h 13mSpirit Airlines
Sat 10/189:48 amSJU - ORD
Nonstop5h 08mSpirit Airlines
Deal found 9/11$217
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
Tue 10/76:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Tue 10/143:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/9$218

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 September 11, 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

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 10/18

6:58 pm-12:59 pm

1 stop17h 01m

Saint Thomas Island Cyril E King

Sat 10/25

11:01 am-11:45 pm

1 stop13h 44m

$214

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 10/8

7:43 pm-12:59 pm

2 stops16h 16m

Saint Thomas Island Cyril E King

Wed 10/15

11:01 am-6:38 pm

1 stop8h 37m

$246

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sun 11/16

5:59 pm-12:28 pm

1 stop16h 29m

Saint Thomas Island Cyril E King

Wed 11/19

1:33 pm-11:42 pm

1 stop12h 09m

$259

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 12/5

5:59 pm-12:28 pm

1 stop16h 29m

Saint Thomas Island Cyril E King

Sun 12/7

1:33 pm-9:00 pm

1 stop9h 27m

$260

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Mon 10/6

7:43 pm-9:56 am

1 stop13h 13m

Saint Thomas Island Cyril E King

Sat 10/11

11:01 am-6:38 pm

1 stop8h 37m

$260

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 10/11

7:43 pm-12:59 pm

2 stops16h 16m

Saint Thomas Island Cyril E King

Tue 10/14

11:01 am-6:38 pm

1 stop8h 37m

$272

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 11/8

5:59 pm-12:28 pm

1 stop16h 29m

Saint Thomas Island Cyril E King

Sat 11/15

1:33 pm-11:42 pm

1 stop12h 09m

$273

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 10/3

1:36 pm-12:47 am

1 stop10h 11m

San Juan Luis Munoz Marin Intl

Mon 10/6

3:03 am-12:10 pm

1 stop10h 07m

$304

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 10/19

8:52 am-2:44 pm

Nonstop4h 52m

San Juan Luis Munoz Marin Intl

Sat 10/25

3:56 pm-8:03 pm

Nonstop5h 07m

$306

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 11/23

6:00 am-5:52 pm

1 stop9h 52m

San Juan Luis Munoz Marin Intl

Wed 11/26

2:26 pm-10:50 pm

1 stop10h 24m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $254). Flying from Chicago O'Hare Intl Airport to Caribbean in June is currently the most expensive (average of $339). 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 September 11, 2025.

When flying from Chicago O'Hare Intl Airport to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 11, 2025.

The most flights from ORD to 0CB are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 September 11, 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
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,023 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Frontier
5.8
Fair
3,177 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 $306, Spirit Airlines can have you in Caribbean from Chicago O'Hare Intl Airport in 4h 52m. The distance between Chicago O'Hare Intl Airport and Caribbean is about 2073 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 Arajet. According to our data, you can fly for as low as $98. Users have also found prices from $100 and $126 on Spirit Airlines and Frontier, 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 - Montego Bay Sangster Intl or Chicago O'Hare Intl - Punta Cana 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: Spirit Airlines (79%), American Airlines (77%), Alaska Airlines (77%).

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

    On average you can expect to pay $463 for a flight from Chicago O'Hare Intl Airport to Caribbean. The cheapest flight overall is $127 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $177.

  • 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 $254). Flying from Chicago O'Hare Intl Airport to Caribbean in June is currently the most expensive (average of $339). 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$381FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$373FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$193Average$458FlexibilityNo cancel feeOn-time70%
DeltaCheapest$212Average$633FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$226Average$664FlexibilityNo cancel feeOn-time69%
ArajetCheapest$235Average$320FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$261Average$482FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$335Average$750FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$347Average$648FlexibilityNo cancel feeOn-time71%

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