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O'Hare Intl

$95+ Cheap flights from Caribbean Islands 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Caribbean Islands to O'Hare Intl

Cheapest flights from Caribbean Islands to O'Hare Intl
Explore the most affordable flight options available from Caribbean Islands to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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 12/2511:38 amSJU - ORD
1 stop9h 24mSpirit Airlines
Thu 1/17:20 amORD - SJU
1 stop16h 52mSpirit Airlines
Deal found 12/22$186
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:30 amSJU - ORD
1 stop13h 03mFrontier
Sat 1/108:27 pmORD - SJU
1 stop10h 27mFrontier
Deal found 12/21$192
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/317:30 amSJU - ORD
1 stop13h 03mFrontier
Wed 2/188:30 amORD - SJU
1 stop14h 13mFrontier
Deal found 12/22$194
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2411:38 amSJU - ORD
1 stop9h 24mMultiple Airlines
Thu 1/112:39 pmORD - SJU
1 stop9h 58mMultiple Airlines
Deal found 12/21$195
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:28 pmSJU - ORD
1 stop8h 02mSpirit Airlines
Mon 1/59:09 pmORD - SJU
1 stop18h 14mSpirit Airlines
Deal found 12/21$196
This Priceline deal was found by Cheapflights users on 12/22. 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.
Wed 12/317:30 amSJU - ORD
1 stop13h 03mMultiple Airlines
Tue 1/610:55 amORD - SJU
1 stop11h 19mMultiple Airlines
Deal found 12/22$197
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:30 amSJU - ORD
1 stop13h 03mMultiple Airlines
Mon 1/56:45 amORD - SJU
1 stop10h 04mMultiple Airlines
Deal found 12/20$198
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:28 pmSJU - ORD
1 stop8h 02mMultiple Airlines
Wed 12/312:15 pmORD - SJU
1 stop8h 14mMultiple Airlines
Deal found 12/20$201
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:30 amSJU - ORD
1 stop13h 03mFrontier
Sun 1/46:00 amORD - SJU
1 stop7h 01mFrontier
Deal found 12/21$206
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Wed 12/312:15 pmORD - SJU
1 stop8h 14mMultiple Airlines
Deal found 12/21$213
This Mytrip deal was found by Cheapflights users on 12/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:00 pmPUJ - ORD
Nonstop5h 10mArajet
Sat 1/310:27 amORD - PUJ
Nonstop4h 45mArajet
Deal found 12/22$242
This Expedia deal was found by Cheapflights users on 12/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/277:17 amPUJ - ORD
Nonstop5h 10mArajet
Sat 1/310:27 amORD - PUJ
Nonstop4h 45mArajet
Deal found 12/22$274

Find flight deals from Caribbean Islands to O'Hare Intl

Keep the following information in mind while searching for Caribbean Islands to O'Hare Intl flight deals. Data was last updated December 23, 2025.

Round-trip from

$165
(SmartFares)

One-way from

$95
(Super.com)
From Caribbean Islands to Chicago O'Hare Intl
Search Deals
One-way flight from Caribbean Islands to Chicago O'Hare Intl
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands 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 December 23, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Chicago O'Hare Intl Airport that are best for you.

Fly from

Caribbean Islands

Fly to

O'Hare Intl

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/29

11:06 am-7:36 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 2/1

7:45 am-6:05 pm

1 stop8h 20m

$179

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/19

4:25 pm-8:12 pm

1 stop29h 47m

Chicago O'Hare Intl

Mon 2/23

3:50 pm-9:54 am

1 stop16h 04m

$180

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/15

11:06 am-7:36 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 1/18

9:15 am-7:26 pm

1 stop8h 11m

$183

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/15

1:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Sun 1/18

12:17 pm-6:49 pm

Nonstop4h 32m

$187

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/21

12:30 pm-7:26 pm

1 stop7h 56m

Chicago O'Hare Intl

Fri 5/22

3:15 pm-1:59 am

1 stop9h 44m

$231

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Wed 2/4

4:40 pm-11:47 pm

1 stop9h 07m

Chicago O'Hare Intl

Wed 2/11

5:15 am-3:33 pm

1 stop8h 18m

$232

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/22

12:30 pm-7:26 pm

1 stop7h 56m

Chicago O'Hare Intl

Tue 6/2

3:15 pm-12:59 am

1 stop8h 44m

$237

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Sat 2/7

4:40 pm-11:47 pm

1 stop9h 07m

Chicago O'Hare Intl

Mon 2/9

5:15 am-3:33 pm

1 stop8h 18m

$245

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 3/11

1:30 am-10:05 am

1 stop9h 35m

Chicago O'Hare Intl

Sun 3/15

12:20 pm-8:26 pm

1 stop7h 06m

$260

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 1/16

7:44 pm-7:41 pm

2 stops25h 57m

Chicago O'Hare Intl

Mon 1/19

8:36 pm-11:33 pm

2 stops24h 57m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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

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

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

Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Chicago O'Hare Intl Airport (average of $121). Flying from Caribbean Islands to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $175). 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 EPX to ORD?

Find hourly flight availability from Caribbean Islands 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 December 23, 2025.

It’s typically best to fly out from Caribbean Islands to Chicago O'Hare Intl Airport in the evening. Doing so could potentially save you 26% on the flight price compared to flying in the afternoon, which is usually more expensive.

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

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

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

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

Explore weekly flight availability from Caribbean Islands 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 December 23, 2025.

The most flights from zzEPX to ORD 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 (10 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 December 23, 2025.
Get a feel of what it's like to fly with Copa Airlines, United Airlines, and American Airlines from Caribbean Islands to Chicago O'Hare Intl Airport by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.6
Good
1,557 reviews

Entertainment

6.8

Crew

8.1

Overall

7.6

Food

6.8

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Copa Airlines
7.6
Good
1,557 reviews
Copa Airlines
7.6
Good
1,557 reviews

Entertainment

6.8

Crew

8.1

Overall

7.6

Food

6.8

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
United Airlines
7.4
Good
9,109 reviews
Copa Airlines
7.6
Good
1,557 reviews

Entertainment

6.8

Crew

8.1

Overall

7.6

Food

6.8

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
American Airlines
7.2
Good
11,050 reviews
Copa Airlines
7.6
Good
1,557 reviews

Entertainment

6.8

Crew

8.1

Overall

7.6

Food

6.8

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Spirit Airlines
6.3
Okay
8,194 reviews
Copa Airlines
7.6
Good
1,557 reviews

Entertainment

6.8

Crew

8.1

Overall

7.6

Food

6.8

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Frontier
5.8
Fair
3,073 reviews
Copa Airlines
7.6
Good
1,557 reviews

Entertainment

6.8

Crew

8.1

Overall

7.6

Food

6.8

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands 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.

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

    JetBlue, Frontier, and Spirit Airlines can get you from Caribbean Islands to Chicago O'Hare Intl Airport in just under 5h 15m. Your travel time can differ by up to 24h 32m. The distance from Caribbean Islands to Chicago O'Hare Intl Airport 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 Caribbean Islands to Chicago O'Hare Intl Airport one-way?

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $71. Users have also found prices from $90 and $94 on Frontier and Spirit Airlines, respectively.

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

    When deciding which route to take from Caribbean Islands to Chicago O'Hare Intl Airport consider Punta Cana - Chicago O'Hare Intl, San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl or Santo Domingo Las Americas - Chicago O'Hare Intl as they are the most popular.

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

    No one likes to see their flight delayed. When booking a flight from Caribbean Islands to Chicago O'Hare Intl Airport consider choosing Spirit Airlines (87%), Air Canada (82%) or United Airlines (82%) as they are the most reliable in getting you off to your destination on time.

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

    While on average a flight from Caribbean Islands to Chicago O'Hare Intl Airport is generally $455, our data shows the cheapest flight currently is $108. When looking at the most popular route, (Punta Cana - Chicago O'Hare Intl), you can expect to pay $193 for that flight.

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Chicago O'Hare Intl Airport (average of $121). Flying from Caribbean Islands to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $175). 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
Gurnee
Elgin
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Lake Geneva
Bridgeview
Kenosha
Warrenville
Waukegan
Aurora
Evanston

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Caribbean Islands to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
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Baltimore to Midway flights
Miami to O'Hare Intl flights
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Raleigh to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Hobby to Midway flights
Minneapolis to Midway flights
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Cleveland to O'Hare Intl flights
Mexico City to O'Hare Intl flights
Orlando to Midway flights
Denver to Midway flights
Dulles Intl to Midway flights
Boston to Midway flights
Portland to O'Hare Intl flights
Columbus to O'Hare Intl flights
West Palm Beach to O'Hare Intl flights
Detroit to O'Hare Intl flights
George Bush Intcntl to Midway flights
San Francisco to Midway flights

Top 6 airlines flying from Caribbean Islands to O'Hare Intl

Discover the top 6 airlines that operate flights from Caribbean Islands 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$120Average$228FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$138Average$329FlexibilityNo cancel feeOn-time65%
FrontierCheapest$138Average$349FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$626FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$258Average$556FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$271Average$519FlexibilityNo cancel feeOn-time69%

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