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O'Hare Intl

$114+ Cheap flights from Caribbean to O'Hare Intl (ORD)

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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheap flight deals from Caribbean to O'Hare Intl

Keep the following information in mind while searching for Caribbean to O'Hare Intl flight deals. Data was last updated July 30, 2025.

Round-trip from

$230
(KAYAK)

One-way from

$114
(SmartFares)

Popular in

June

Cheapest in

January

Average price

$301

Good round-trip deal

$273 or less

Good one-way deal

$190 or less
From Caribbean to Chicago O'Hare Intl
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One-way flight from Caribbean to Chicago O'Hare Intl
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Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Caribbean to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Caribbean to Chicago O'Hare Intl.
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Find flight deals from Caribbean to O'Hare Intl

Cheapest flights from Caribbean to O'Hare Intl
Explore the most affordable flight options available from Caribbean to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

This KAYAK deal was found by Cheapflights users on 7/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/73:00 pmSJU - ORD
Nonstop5h 20mAmerican Airlines
Wed 10/87:11 amORD - SJU
2 stops15h 48mAmerican Airlines
Deal found 7/29$230
This CheapOair deal was found by Cheapflights users on 7/29. 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.
Thu 9/1811:59 amSJU - ORD
1 stop11h 49mSpirit Airlines
Wed 9/246:44 pmORD - SJU
1 stop15h 20mSpirit Airlines
Deal found 7/29$231
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Fri 8/1510:16 pmSJU - ORD
1 stop12h 06mMultiple Airlines
Thu 8/217:46 pmORD - SJU
1 stop12h 13mMultiple Airlines
Deal found 7/29$234
This eDestinos deal was found by Cheapflights users on 7/28. 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.
Thu 8/143:40 amSJU - ORD
1 stop29h 27mFrontier
Mon 8/187:45 amORD - SJU
1 stop7h 58mFrontier
Deal found 7/28$252
This Frontier deal was found by Cheapflights users on 7/30. 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.
Fri 9/193:32 amBQN - ORD
1 stop12h 45mFrontier
Fri 10/38:49 pmORD - BQN
1 stop13h 07mFrontier
Deal found 7/30$258
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Fri 8/224:24 pmSTT - ORD
1 stop6h 58mSpirit Airlines
Mon 8/256:56 amORD - STT
1 stop7h 23mSpirit Airlines
Deal found 7/29$270
This CheapOair deal was found by Cheapflights users on 7/28. 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 8/274:05 pmPUJ - ORD
1 stop8h 54mSpirit Airlines
Wed 9/35:05 amORD - PUJ
1 stop8h 55mSpirit Airlines
Deal found 7/28$276
This Cheapflightsfares deal was found by Cheapflights users on 7/28. 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 8/145:45 pmPUJ - ORD
Nonstop5h 08mFrontier
Mon 8/186:45 amORD - PUJ
Nonstop4h 40mFrontier
Deal found 7/28$284
This Booking.com deal was found by Cheapflights users on 7/29. 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.
Thu 8/285:05 pmSDQ - ORD
1 stop7h 54mSpirit Airlines
Thu 9/45:05 amORD - SDQ
1 stop9h 55mSpirit Airlines
Deal found 7/29$292
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1312:19 pmMBJ - ORD
1 stop6h 48mSpirit Airlines
Wed 10/155:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Deal found 7/29$294
This Orbitz deal was found by Cheapflights users on 7/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/144:05 pmPUJ - ORD
1 stop8h 54mMultiple Airlines
Mon 8/186:45 amORD - PUJ
Nonstop4h 40mMultiple Airlines
Deal found 7/29$328
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 10/93:21 pmPUJ - ORD
Nonstop5h 15mAmerican Airlines
Wed 10/155:20 amORD - PUJ
1 stop9h 09mAmerican Airlines
Deal found 7/30$337

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to O'Hare Intl 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 July 30, 2025.
Use the filters below to find and compare flights from Caribbean to Chicago O'Hare Intl Airport that are best for you.

Fly from

Caribbean

Fly to

O'Hare Intl

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 10/7

3:00 pm-7:20 pm

Nonstop5h 20m

Chicago O'Hare Intl

Wed 10/8

7:11 am-11:59 pm

2 stops15h 48m

$230

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 9/18

11:59 am-10:48 pm

1 stop11h 49m

Chicago O'Hare Intl

Wed 9/24

6:44 pm-11:04 am

1 stop15h 20m

$231

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

Thu 8/21

7:46 pm-8:59 am

1 stop12h 13m

$234

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 8/14

3:40 am-8:07 am

1 stop29h 27m

Chicago O'Hare Intl

Mon 8/18

7:45 am-4:43 pm

1 stop7h 58m

$252

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Fri 9/19

3:32 am-3:17 pm

1 stop12h 45m

Chicago O'Hare Intl

Fri 10/3

8:49 pm-10:56 am

1 stop13h 07m

$258

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Fri 8/22

4:24 pm-10:22 pm

1 stop6h 58m

Chicago O'Hare Intl

Mon 8/25

6:56 am-3:19 pm

1 stop7h 23m

$270

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 8/27

4:05 pm-11:59 pm

1 stop8h 54m

Chicago O'Hare Intl

Wed 9/3

5:05 am-3:00 pm

1 stop8h 55m

$276

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 8/14

5:45 pm-9:53 pm

Nonstop5h 08m

Chicago O'Hare Intl

Mon 8/18

6:45 am-12:25 pm

Nonstop4h 40m

$284

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 8/28

5:05 pm-11:59 pm

1 stop7h 54m

Chicago O'Hare Intl

Thu 9/4

5:05 am-4:00 pm

1 stop9h 55m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 8/13

12:19 pm-7:07 pm

1 stop6h 48m

Chicago O'Hare Intl

Wed 10/15

5:05 am-11:05 am

1 stop6h 00m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Caribbean 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 Caribbean to Chicago O'Hare Intl Airport

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

Currently, August is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $245). Flying from Caribbean to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 CB to ORD?

Find hourly flight availability from Caribbean to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 30, 2025.

When flying from Caribbean to Chicago O'Hare Intl Airport, 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 Caribbean to Chicago O'Hare Intl Airport

Explore weekly flight availability from Caribbean to O'Hare Intl. 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 July 30, 2025.

The most flights from 0CB to ORD are scheduled on a Monday (9 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (8 on average).

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated July 30, 2025.
Get a feel of what it's like to fly with Delta, Copa Airlines, and United Airlines from Caribbean to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Copa Airlines
7.5
Good
1,493 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
JetBlue
7.3
Good
2,913 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

Related info for your journey

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

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

    The cheapest airlines for a one-way flight from Caribbean to Chicago O'Hare Intl Airport are Spirit Airlines ($114), Frontier ($119), and American Airlines ($187).

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

    While some choose either Santo Domingo Las Americas - Chicago O'Hare Intl or Punta Cana - Chicago O'Hare Intl, San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl is the most popular route from Caribbean to Chicago O'Hare Intl Airport.

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

    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 Caribbean to Chicago O'Hare Intl Airport on time: Spirit Airlines (99%), Air Canada (92%), United Airlines (92%).

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

    Looking for the cheapest flight from Caribbean to Chicago O'Hare Intl Airport? While on average our users pay $1,810, our data indicates the cheapest price to be $127. The most popular route (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), is priced around $177.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $245). Flying from Caribbean to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Beloit
Hoffman Estates
Skokie
Naperville
Des Plaines
Elgin
Arlington Heights
Elk Grove Village
Racine
Rockford
Tinley Park
Orland Park
Merrillville
Downers Grove
Evanston
Lake Geneva
Gurnee
Joliet

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Caribbean to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
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Burbank to O'Hare Intl flights
Miami to O'Hare Intl flights
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Mexico City to O'Hare Intl flights
San Francisco to Midway flights
Orlando to O'Hare Intl flights
San Diego to O'Hare Intl flights
Hobby to O'Hare Intl flights
San Jose to O'Hare Intl flights
Portland to O'Hare Intl flights
Los Angeles to Midway flights
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Minneapolis to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Philadelphia to Midway flights
Tampa to O'Hare Intl flights
Nashville to O'Hare Intl flights
Boston to Midway flights
Oakland to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Minneapolis to Midway flights

Top 6 airlines flying from Caribbean to O'Hare Intl

Discover the top 6 airlines that operate flights from Caribbean to O'Hare Intl. 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$137Average$293FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$340FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$440FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$219Average$575FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$431FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$329Average$530FlexibilityNo cancel feeOn-time71%

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