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O'Hare Intl

$109+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Nov 4 — Nov 111
Tue 11/4
Tue 11/11
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 October 5, 2025.

Round-trip from

$204
(Kiwi.com)

One-way from

$109
(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 October 5, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/4. 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 10/239:06 pmSJU - ORD
1 stop13h 16mMultiple Airlines
Sat 10/258:40 amORD - SJU
1 stop9h 18mMultiple Airlines
Deal found 10/4$204
This Cheapflightsfares deal was found by Cheapflights users on 10/4. 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 12/42:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Mon 12/86:55 amORD - SJU
Nonstop4h 38mSpirit Airlines
Deal found 10/4$206
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 10/244:51 pmSJU - ORD
1 stop20h 54mMultiple Airlines
Wed 10/294:03 pmORD - SJU
1 stop10h 00mMultiple Airlines
Deal found 10/5$210
This Frontier deal was found by Cheapflights users on 10/5. 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 10/243:05 pmSJU - ORD
1 stop9h 34mFrontier
Wed 10/296:40 amORD - SJU
1 stop10h 14mFrontier
Deal found 10/5$211
This Frontier deal was found by Cheapflights users on 10/4. 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 10/243:05 pmSJU - ORD
1 stop9h 34mFrontier
Mon 10/276:40 amORD - SJU
1 stop7h 44mFrontier
Deal found 10/4$212
This Kiwi.com deal was found by Cheapflights users on 10/3. 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 10/226:22 amSJU - ORD
1 stop11h 51mMultiple Airlines
Sun 10/267:43 pmORD - SJU
1 stop18h 33mMultiple Airlines
Deal found 10/3$215
This Cheapflightsfares deal was found by Cheapflights users on 10/5. 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 12/42:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Tue 12/96:55 amORD - SJU
Nonstop4h 38mSpirit Airlines
Deal found 10/5$216
This Frontier deal was found by Cheapflights users on 10/4. 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 10/239:06 pmSJU - ORD
2 stops14h 35mFrontier
Mon 10/276:40 amORD - SJU
1 stop7h 44mFrontier
Deal found 10/4$217
This Frontier deal was found by Cheapflights users on 10/3. 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.
Sat 10/181:26 pmSJU - ORD
1 stop8h 22mFrontier
Sat 10/258:40 amORD - SJU
1 stop9h 18mFrontier
Deal found 10/3$219
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 10/249:00 amSJU - ORD
1 stop7h 58mMultiple Airlines
Sat 10/258:40 amORD - SJU
1 stop9h 18mMultiple Airlines
Deal found 10/4$221
This Priceline deal was found by Cheapflights users on 10/4. 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 12/186:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Sat 1/107:00 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 10/4$241
This eDestinos deal was found by Cheapflights users on 10/3. 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.
Sat 10/183:57 pmPUJ - ORD
1 stop8h 48mSpirit Airlines
Sun 10/265:05 amORD - PUJ
1 stop8h 55mSpirit Airlines
Deal found 10/3$258

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 October 5, 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

Wed 11/19

3:34 pm-9:52 pm

1 stop8h 18m

Chicago O'Hare Intl

Wed 12/3

11:25 am-11:54 pm

1 stop10h 29m

$284

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 10/30

3:54 pm-1:03 am

1 stop10h 09m

Chicago O'Hare Intl

Wed 11/5

5:10 am-3:30 pm

1 stop8h 20m

$291

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 10/18

12:37 pm-11:45 pm

2 stops12h 08m

Chicago O'Hare Intl

Sun 10/26

5:05 am-3:00 pm

1 stop8h 55m

$314

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Mon 10/27

4:20 pm-7:41 am

1 stop16h 21m

Chicago O'Hare Intl

Fri 10/31

9:30 am-3:02 pm

Nonstop4h 32m

$315

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 11/26

5:20 pm-6:26 pm

1 stop27h 06m

Chicago O'Hare Intl

Wed 12/3

8:45 am-5:25 pm

1 stop6h 40m

$324

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 11/26

12:56 pm-8:56 am

1 stop22h 00m

Chicago O'Hare Intl

Thu 12/4

2:00 pm-5:25 pm

1 stop25h 25m

$324

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 11/26

5:20 pm-8:56 am

1 stop17h 36m

Chicago O'Hare Intl

Tue 12/2

12:45 pm-5:25 pm

1 stop26h 40m

$324

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 12/3

3:10 pm-8:34 am

2 stops19h 24m

Chicago O'Hare Intl

Sun 12/7

6:30 pm-1:55 pm

1 stop17h 25m

$339

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 11/22

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Fri 11/28

6:00 am-4:31 pm

2 stops32h 31m

$339

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 12/3

3:10 pm-8:34 am

2 stops19h 24m

Chicago O'Hare Intl

Mon 12/8

5:59 pm-1:55 pm

2 stops17h 56m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/4

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 October 5, 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 October 5, 2025.

The most flights from zzEPX to ORD are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 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 October 5, 2025.
Get a feel of what it's like to fly with Delta, 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.
Delta
8.0
Very good
7,970 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,970 reviews
Delta
8.0
Very good
7,970 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,953 reviews
Delta
8.0
Very good
7,970 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
11,041 reviews
Delta
8.0
Very good
7,970 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Spirit Airlines
6.3
Okay
8,075 reviews
Delta
8.0
Very good
7,970 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Frontier
5.8
Fair
3,147 reviews
Delta
8.0
Very good
7,970 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

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, Spirit Airlines, and United Airlines can get you from Caribbean Islands to Chicago O'Hare Intl Airport in just under 8h 18m. Your travel time can differ by up to 8h 03m. 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 Arajet. According to our data, you can fly for as low as $112. Users have also found prices from $118 and $120 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, Santo Domingo Las Americas - Chicago O'Hare Intl or Saint Thomas Island Cyril E King - 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 (84%), Air Canada (78%) or United Airlines (78%) 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 $507, our data shows the cheapest flight currently is $108. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $215 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 Chicago O'Hare Intl Airport?

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

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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Minneapolis to Midway flights
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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 October 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$136Average$308FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$339FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$448FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$257Average$557FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$260Average$460FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$338Average$582FlexibilityNo cancel feeOn-time71%

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