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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 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Mar 16 — Mar 231
Mon 3/16
Mon 3/23
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 February 14, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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.
Thu 2/2612:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/212:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/11$146
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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.
Fri 2/2712:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/212:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/11$162
This eDestinos deal was found by Cheapflights users on 2/14. 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 2/194:36 pm
SJU
-
ORD
1 stop9h 11m
Spirit Airlines
Mon 2/235:15 am
ORD
-
SJU
1 stop8h 16m
Spirit Airlines
Deal found 2/14$174
This Cheapflightsfares deal was found by Cheapflights users on 2/12. 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 3/121:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/1610:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Deal found 2/12$177
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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.
Fri 5/812:30 pm
SJU
-
ORD
Nonstop5h 08m
Spirit Airlines
Mon 5/1112:22 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/11$178
This Orbitz deal was found by Cheapflights users on 2/10. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Tue 9/112:22 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/10$179
This CheapOair deal was found by Cheapflights users on 2/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:32 pm
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Tue 3/38:30 am
ORD
-
SJU
1 stop14h 13m
Multiple Airlines
Deal found 2/11$180
This eDestinos deal was found by Cheapflights users on 2/14. 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 4/307:30 pm
PUJ
-
ORD
Nonstop5h 10m
Arajet
Mon 5/44:30 am
ORD
-
PUJ
Nonstop4h 45m
Arajet
Deal found 2/14$208
This Expedia deal was found by Cheapflights users on 2/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:30 pm
PUJ
-
ORD
Nonstop5h 10m
Arajet
Mon 4/204:30 am
ORD
-
PUJ
Nonstop4h 45m
Arajet
Deal found 2/10$230
This Spirit deal was found by Cheapflights users on 2/11. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:47 pm
PUJ
-
ORD
1 stop8h 00m
Spirit Airlines
Sun 3/15:15 am
ORD
-
PUJ
1 stop9h 21m
Spirit Airlines
Deal found 2/11$236
This American Airlines deal was found by Cheapflights users on 2/13. 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 5/71:15 pm
MBJ
-
ORD
Nonstop4h 40m
American Airlines
Mon 5/118:05 am
ORD
-
MBJ
Nonstop4h 08m
American Airlines
Deal found 2/13$241
This CheapOair deal was found by Cheapflights users on 2/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/184:35 pm
STT
-
ORD
1 stop7h 42m
Spirit Airlines
Tue 3/246:10 pm
ORD
-
STT
1 stop20h 18m
Spirit Airlines
Deal found 2/11$242

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 February 14, 2026.

Round-trip from

$146
(Cheapflightsfares)

One-way from

$95
(Cheapflightsfares)
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 February 14, 2026.
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 2/26

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Mon 3/2

12:17 pm-6:49 pm

Nonstop4h 32m

$146

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 4/23

3:08 am-2:17 pm

1 stop12h 09m

Chicago O'Hare Intl

Sun 4/26

12:22 pm-5:54 pm

Nonstop4h 32m

$196

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 3/11

6:30 am-3:38 pm

1 stop10h 08m

Chicago O'Hare Intl

Tue 3/17

8:56 pm-2:29 am

Nonstop4h 33m

$198

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/8

12:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Mon 5/11

5:15 am-2:31 pm

1 stop8h 16m

$211

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 3/12

6:30 am-3:28 pm

1 stop9h 58m

Chicago O'Hare Intl

Tue 3/17

8:56 pm-2:29 am

Nonstop4h 33m

$217

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 3/5

11:52 am-6:18 pm

1 stop8h 26m

Chicago O'Hare Intl

Mon 3/9

9:18 am-5:58 pm

1 stop7h 40m

$231

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 2/27

5:47 pm-11:47 pm

1 stop8h 00m

Chicago O'Hare Intl

Sun 3/1

5:15 am-4:36 pm

1 stop9h 21m

$236

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 6/4

2:30 pm-6:35 pm

Nonstop5h 05m

Chicago O'Hare Intl

Mon 6/8

10:30 am-4:20 pm

Nonstop4h 50m

$237

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/7

1:15 pm-5:55 pm

Nonstop4h 40m

Chicago O'Hare Intl

Mon 5/11

8:05 am-12:13 pm

Nonstop4h 08m

$241

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/28

3:43 pm-11:12 pm

1 stop8h 29m

Chicago O'Hare Intl

Wed 6/3

5:30 am-2:28 pm

1 stop7h 58m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

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, February is the cheapest month in which you can book a flight from Caribbean Islands to Chicago O'Hare Intl Airport (average of $111). Flying from Caribbean Islands to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $157). 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 February 14, 2026.

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 50% on the flight price compared to flying at noon, 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 February 7, 2026.

Travelers seeking maximum savings on their Caribbean Islands to Chicago O'Hare Intl Airport flight should consider departing on Friday evenings 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 February 14, 2026.

The most flights from zzEPX to ORD are scheduled on a Friday (12 on average). You will have fewer flight options on Wednesday, 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 February 14, 2026.
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
7.5
Good
1,558 reviews

Comfort

7.4

Entertainment

6.8

Overall

7.5

Food

6.8

Crew

8.1

Boarding

7.8

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
7.5
Good
1,558 reviews
Copa Airlines
7.5
Good
1,558 reviews

Comfort

7.4

Entertainment

6.8

Overall

7.5

Food

6.8

Crew

8.1

Boarding

7.8

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
9,295 reviews
Copa Airlines
7.5
Good
1,558 reviews

Comfort

7.4

Entertainment

6.8

Overall

7.5

Food

6.8

Crew

8.1

Boarding

7.8

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
11,296 reviews
Copa Airlines
7.5
Good
1,558 reviews

Comfort

7.4

Entertainment

6.8

Overall

7.5

Food

6.8

Crew

8.1

Boarding

7.8

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
8,452 reviews
Copa Airlines
7.5
Good
1,558 reviews

Comfort

7.4

Entertainment

6.8

Overall

7.5

Food

6.8

Crew

8.1

Boarding

7.8

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
5.7
Fair
3,051 reviews
Copa Airlines
7.5
Good
1,558 reviews

Comfort

7.4

Entertainment

6.8

Overall

7.5

Food

6.8

Crew

8.1

Boarding

7.8

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?

    Spirit Airlines, American Airlines, and Southwest can get you from Caribbean Islands to Chicago O'Hare Intl Airport in just under 4h 40m. Your travel time can differ by up to 14h 10m. The distance from Caribbean Islands to Chicago O'Hare Intl Airport is about 1724 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 $74. Users have also found prices from $92 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 San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl, Punta Cana - Chicago O'Hare Intl or Nassau Intl - 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 Air Canada (83%), United Airlines (83%) or Air New Zealand (83%) 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 $458, our data shows the cheapest flight currently is $122. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $147 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, February is the cheapest month in which you can book a flight from Caribbean Islands to Chicago O'Hare Intl Airport (average of $111). Flying from Caribbean Islands to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $157). 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
Naperville
Gurnee
Elgin
Hoffman Estates
Beloit
Delavan
Oak Brook
Des Plaines
Downers Grove
Elk Grove Village
Skokie
Libertyville
Lake Geneva
Waukegan
Bridgeview
Kenosha
Warrenville
Aurora

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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Newark to Midway flights
Hobby to O'Hare Intl flights
Los Angeles to Midway flights
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LaGuardia to Midway flights
Charlotte to O'Hare Intl flights
Hobby to Midway flights
Minneapolis to O'Hare Intl flights
Dulles Intl to Midway flights
Raleigh to O'Hare Intl flights
Atlanta to Midway flights
Baltimore to Midway flights
Santa Ana to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Austin to O'Hare Intl flights
Reagan-National to Midway flights
Orlando to O'Hare Intl flights
San Francisco to Midway flights
Love Field to O'Hare Intl flights
San Diego to O'Hare Intl flights
Philadelphia to Midway flights
Fort Lauderdale to O'Hare Intl flights
Mexico City to O'Hare Intl flights
Minneapolis to Midway flights
Tampa to O'Hare Intl flights
Portland to O'Hare Intl flights
Orlando to Midway flights
San Jose to O'Hare Intl flights
Hartford to O'Hare Intl flights
Miami to O'Hare Intl flights
Boston to Midway flights
Detroit to O'Hare Intl flights
George Bush Intcntl 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 February 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$626FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$122Average$334FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$131Average$201FlexibilityNo cancel feeOn-time62%
FrontierCheapest$137Average$335FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$256Average$520FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$544FlexibilityNo cancel feeOn-time71%

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