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O'Hare Intl

$121+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
May 19 — May 261
Mon 5/19
Mon 5/26
1 adult, Economy
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Cheap 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 May 14, 2025.

Round-trip from

$200
(Cheapflightsfares)

One-way from

$121
(Kiwi.com)
From Caribbean Islands to Chicago O'Hare Intl
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One-way flight from Caribbean Islands to Chicago O'Hare Intl
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Find 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 May 14, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 5/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/296:09 amSJU - ORD
Nonstop5h 16mSpirit Airlines
Mon 6/211:30 amORD - SJU
Nonstop4h 46mSpirit Airlines
Deal found 5/14$200
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/55:54 pmPUJ - ORD
Nonstop5h 09mFrontier
Sun 6/86:45 amORD - PUJ
Nonstop4h 44mFrontier
Deal found 5/13$227
This CheapOair deal was found by Cheapflights users on 5/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2310:00 amSJU - ORD
1 stop15h 20mMultiple Airlines
Tue 5/2711:30 amORD - SJU
Nonstop4h 46mMultiple Airlines
Deal found 5/12$270
This SmartFares deal was found by Cheapflights users on 5/13. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/712:07 pmMBJ - ORD
1 stop11h 58mSpirit Airlines
Sat 6/215:05 amORD - MBJ
1 stop5h 57mSpirit Airlines
Deal found 5/13$295
This Priceline deal was found by Cheapflights users on 5/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/512:42 pmPUJ - ORD
1 stop11h 47mMultiple Airlines
Sun 6/86:45 amORD - PUJ
Nonstop4h 44mMultiple Airlines
Deal found 5/13$295
This Frontier deal was found by Cheapflights users on 5/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/283:21 pmSJU - ORD
1 stop9h 49mFrontier
Sun 8/317:15 amORD - SJU
1 stop7h 22mFrontier
Deal found 5/14$298
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/64:35 pmPUJ - ORD
1 stop7h 55mUnited Airlines
Fri 8/89:23 amORD - PUJ
Nonstop4h 42mUnited Airlines
Deal found 5/13$317
This Cheapflightsfares deal was found by Cheapflights users on 5/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/252:45 amSDQ - ORD
1 stop8h 10mSpirit Airlines
Tue 9/231:03 pmORD - SDQ
1 stop12h 07mSpirit Airlines
Deal found 5/13$325
This Cheapflightsfares deal was found by Cheapflights users on 5/12. 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.
Fri 6/612:42 pmPUJ - ORD
1 stop8h 21mSpirit Airlines
Wed 6/115:05 amORD - PUJ
1 stop8h 12mSpirit Airlines
Deal found 5/12$329
This Cheapflightsfares deal was found by Cheapflights users on 5/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1211:29 amSTI - ORD
1 stop13h 16mSpirit Airlines
Tue 6/174:45 pmORD - STI
1 stop16h 44mSpirit Airlines
Deal found 5/13$342
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/103:35 pmSDQ - ORD
1 stop27h 06mMultiple Airlines
Tue 6/171:43 pmORD - SDQ
1 stop25h 46mMultiple Airlines
Deal found 5/13$354
This American Airlines deal was found by Cheapflights users on 5/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1612:05 pmPUJ - ORD
1 stop12h 52mAmerican Airlines
Wed 8/135:00 amORD - PUJ
1 stop6h 50mAmerican Airlines
Deal found 5/14$390

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 May 14, 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 5/29

6:09 am-10:25 am

Nonstop5h 16m

Chicago O'Hare Intl

Mon 6/2

11:30 am-5:16 pm

Nonstop4h 46m

$200

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 6/5

5:54 pm-10:03 pm

Nonstop5h 09m

Chicago O'Hare Intl

Sun 6/8

6:45 am-12:29 pm

Nonstop4h 44m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/23

10:00 am-12:20 am

1 stop15h 20m

Chicago O'Hare Intl

Tue 5/27

11:30 am-5:16 pm

Nonstop4h 46m

$270

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 6/7

12:07 pm-12:05 am

1 stop11h 58m

Chicago O'Hare Intl

Sat 6/21

5:05 am-11:02 am

1 stop5h 57m

$295

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 6/5

12:42 pm-11:29 pm

1 stop11h 47m

Chicago O'Hare Intl

Sun 6/8

6:45 am-12:29 pm

Nonstop4h 44m

$295

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/30

3:40 am-12:04 am

1 stop21h 24m

Chicago O'Hare Intl

Sat 6/7

5:08 pm-2:35 am

1 stop8h 27m

$304

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 8/6

4:35 pm-11:30 pm

1 stop7h 55m

Chicago O'Hare Intl

Fri 8/8

9:23 am-3:05 pm

Nonstop4h 42m

$317

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Mon 8/25

2:45 am-9:55 am

1 stop8h 10m

Chicago O'Hare Intl

Tue 9/23

1:03 pm-2:10 am

1 stop12h 07m

$325

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 6/6

12:42 pm-8:03 pm

1 stop8h 21m

Chicago O'Hare Intl

Wed 6/11

5:05 am-2:17 pm

1 stop8h 12m

$329

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Thu 6/12

11:29 am-11:45 pm

1 stop13h 16m

Chicago O'Hare Intl

Tue 6/17

4:45 pm-10:29 am

1 stop16h 44m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/13

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 $245). Flying from Caribbean Islands 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 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 May 14, 2025.

When flying from Caribbean Islands 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 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 May 14, 2025.

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

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 14, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Caribbean Islands to Chicago by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,290 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Copa Airlines
7.6
Good
1,423 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Aeromexico
7.5
Good
1,699 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

  • 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 Spirit Airlines. According to our data, you can fly for as low as $121. Users have also found prices from $128 and $148 on Frontier and JetBlue, 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, Santo Domingo Las Americas - Chicago O'Hare Intl or Punta Cana - 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 (78%), American Airlines (74%) or Air Canada (73%) 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 $480, our data shows the cheapest flight currently is $119. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $202 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 $245). Flying from Caribbean Islands 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 Caribbean Islands?

Book flights to Caribbean Islands if you plan to visit one of these locations
Schaumburg
Hoffman Estates
Rosemont
Racine
Beloit
Skokie
Naperville
Elgin
Kenosha
Tinley Park
Arlington Heights
Rockford
Orland Park
Joliet
Merrillville
Northbrook
Elk Grove Village
Glenview
Des Plaines
Lake Geneva

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.
LaGuardia to O'Hare Intl flights
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Philadelphia to O'Hare Intl flights
Newark to Midway flights
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Boston to O'Hare Intl flights
LaGuardia to Midway flights
John F Kennedy Intl to Midway flights
Dulles Intl to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Seattle to O'Hare Intl flights
Denver to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
San Francisco to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Atlanta to O'Hare Intl flights
Ontario to O'Hare Intl flights
Hobby to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Tampa to O'Hare Intl flights
Dulles Intl to Midway flights
Austin to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Baltimore to Midway flights
San Diego to O'Hare Intl flights
Atlanta to Midway flights
Burbank to O'Hare Intl flights
Portland to O'Hare Intl flights
Hobby to Midway flights
Los Angeles to Midway flights
Charlotte to O'Hare Intl flights
Orlando to O'Hare Intl flights
Seattle to Midway flights
Mexico City to O'Hare Intl flights
Miami to O'Hare Intl flights
Minneapolis to Midway flights
Oakland to O'Hare Intl flights
Boston to Midway flights
Minneapolis to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
San Jose to O'Hare Intl flights
Detroit to O'Hare Intl flights
Hartford to O'Hare Intl flights
Philadelphia to Midway flights
Reagan-National 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 May 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$319FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$324FlexibilityNo cancel feeOn-time65%
DeltaCheapest$172Average$496FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$216Average$550FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$421FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$323Average$565FlexibilityNo cancel feeOn-time71%

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