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O'Hare Intl

$76+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Round-trip from

$137
(Kiwi.com)

One-way from

$76
(Mytrip)
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 February 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/246:35 amSJU - ORD
Nonstop5h 23mMultiple Airlines
Mon 4/284:30 pmORD - SJU
1 stop9h 19mMultiple Airlines
Deal found 2/20$137
This eDestinos deal was found by Cheapflights users on 2/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/113:38 amSJU - ORD
1 stop7h 01mSpirit Airlines
Mon 3/178:46 pmORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 2/20$138
This Flightnetwork deal was found by Cheapflights users on 2/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/111:20 amSJU - ORD
1 stop20h 46mFrontier
Mon 5/54:15 pmORD - SJU
1 stop9h 36mFrontier
Deal found 2/20$148
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 4/225:50 pmPUJ - ORD
Nonstop5h 18mFrontier
Mon 4/286:20 amORD - PUJ
Nonstop4h 36mFrontier
Deal found 2/19$210
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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.
Wed 3/1912:07 pmMBJ - ORD
1 stop6h 43mSpirit Airlines
Wed 3/267:21 pmORD - MBJ
1 stop15h 41mSpirit Airlines
Deal found 2/19$263
This Priceline deal was found by Cheapflights users on 2/19. 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.
Tue 4/225:50 pmPUJ - ORD
Nonstop5h 18mMultiple Airlines
Mon 4/285:10 amORD - PUJ
1 stop8h 32mMultiple Airlines
Deal found 2/19$266
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/264:15 pmSJU - ORD
1 stop9h 34mDelta
Sun 3/211:15 amORD - SJU
1 stop10h 31mDelta
Deal found 2/20$271
This OneTravel deal was found by Cheapflights users on 2/18. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/11:14 pmPUJ - ORD
1 stop25h 34mSpirit Airlines
Tue 4/89:08 pmORD - PUJ
1 stop13h 36mSpirit Airlines
Deal found 2/18$298
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/61:44 pmSDQ - ORD
1 stop20h 22mMultiple Airlines
Sun 4/137:49 pmORD - SDQ
1 stop19h 00mMultiple Airlines
Deal found 2/20$358
This Booking.com deal was found by Cheapflights users on 2/18. 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.
Wed 4/302:34 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Fri 5/95:05 amORD - SXM
1 stop7h 56mSpirit Airlines
Deal found 2/18$362
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/88:00 amSDQ - ORD
2 stops16h 11mFrontier
Mon 5/126:40 amORD - SDQ
2 stops16h 15mFrontier
Deal found 2/20$377
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Sun 4/133:50 pmAUA - ORD
1 stop26h 51mSpirit Airlines
Sun 4/205:10 amORD - AUA
1 stop8h 30mSpirit Airlines
Deal found 2/20$383

Find flights from Caribbean Islands to O'Hare Intl within your budget

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 20, 2025.

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 4/24

6:35 am-10:58 am

Nonstop5h 23m

Chicago O'Hare Intl

Mon 4/28

4:30 pm-2:49 am

1 stop9h 19m

$137

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 3/11

3:38 am-9:39 am

1 stop7h 01m

Chicago O'Hare Intl

Mon 3/17

8:46 pm-2:27 am

Nonstop4h 41m

$138

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/1

11:20 am-7:06 am

1 stop20h 46m

Chicago O'Hare Intl

Mon 5/5

4:15 pm-2:51 am

1 stop9h 36m

$148

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 4/22

5:50 pm-10:08 pm

Nonstop5h 18m

Chicago O'Hare Intl

Mon 4/28

6:20 am-11:56 am

Nonstop4h 36m

$210

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 3/19

12:07 pm-6:50 pm

1 stop6h 43m

Chicago O'Hare Intl

Wed 3/26

7:21 pm-11:02 am

1 stop15h 41m

$263

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 4/22

5:50 pm-10:08 pm

Nonstop5h 18m

Chicago O'Hare Intl

Mon 4/28

5:10 am-2:42 pm

1 stop8h 32m

$266

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 4/1

1:14 pm-1:48 pm

1 stop25h 34m

Chicago O'Hare Intl

Tue 4/8

9:08 pm-11:44 am

1 stop13h 36m

$298

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Sun 4/6

1:44 pm-9:06 am

1 stop20h 22m

Chicago O'Hare Intl

Sun 4/13

7:49 pm-3:49 pm

1 stop19h 00m

$358

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 4/30

2:34 pm-12:41 am

1 stop11h 07m

Chicago O'Hare Intl

Fri 5/9

5:05 am-2:01 pm

1 stop7h 56m

$362

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 5/8

8:00 am-11:11 pm

2 stops16h 11m

Chicago O'Hare Intl

Mon 5/12

6:40 am-11:55 pm

2 stops16h 15m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 60 results
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2
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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.

Travel insights for flights from Caribbean Islands to O'Hare Intl

Get recent, data-driven insights about flights from Caribbean Islands to O'Hare Intl including ideal travel times, pricing trends, and more.

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 February 20, 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 February 20, 2025.

The most flights from zzEPX to ORD are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 February 20, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Alaska Airlines 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.
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,510 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

LATAM Airlines
7.5
Good
1,795 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $76. Users have also found prices from $79 and $131 on Frontier and American 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 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 Air Canada (84%), United Airlines (84%) or Air New Zealand (84%) 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 $498, our data shows the cheapest flight currently is $87. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $122 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
Naperville
Rosemont
Schaumburg
Beloit
Racine
Hoffman Estates
Rockford
Tinley Park
Skokie
Arlington Heights
Northbrook
Joliet
Orland Park
Merrillville
Kenosha
Lake Geneva
New Buffalo
Evanston
Des Plaines
Elgin

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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Dulles Intl to Midway flights
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Miami to O'Hare Intl flights
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Portland to O'Hare Intl flights
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Minneapolis to Midway flights
Philadelphia to Midway flights
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Hobby to O'Hare Intl flights
Oakland to O'Hare Intl flights
Hobby to Midway flights
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Top 7 airlines flying from Caribbean Islands to O'Hare Intl

Discover the top 7 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 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$317FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$312FlexibilityNo cancel feeOn-time65%
DeltaCheapest$182Average$445FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$213Average$568FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$389FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$314Average$565FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$568FlexibilityNo cancel feeOn-time70%
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