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O'Hare Intl

$107+ Cheap flights from Caribbean 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 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Find flight deals from Caribbean to O'Hare Intl

Cheapest flights from Caribbean to O'Hare Intl
Explore the most affordable flight options available from Caribbean to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/111:59 amSJU - ORD
1 stop12h 41mMultiple Airlines
Mon 12/155:40 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 11/11$185
This eDestinos deal was found by Cheapflights users on 11/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:00 amSJU - ORD
1 stop13h 33mFrontier
Sun 1/49:05 amORD - SJU
1 stop19h 29mFrontier
Deal found 11/12$186
This Flightnetwork deal was found by Cheapflights users on 11/13. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:31 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Sun 12/145:40 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 11/13$188
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/245:19 pmSJU - ORD
1 stop28h 02mFrontier
Sat 11/295:20 amORD - SJU
1 stop8h 30mFrontier
Deal found 11/12$189
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/44:31 pmSJU - ORD
1 stop7h 53mMultiple Airlines
Mon 12/87:41 pmORD - SJU
2 stops44h 42mMultiple Airlines
Deal found 11/12$191
This Gotogate deal was found by Cheapflights users on 11/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Mon 12/82:26 pmORD - SJU
1 stop10h 24mMultiple Airlines
Deal found 11/10$193
This Priceline deal was found by Cheapflights users on 11/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Fri 12/127:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 11/12$196
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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.
Sat 11/2211:55 amSJU - ORD
1 stop13h 34mSpirit Airlines
Fri 11/2811:40 amORD - SJU
1 stop8h 10mSpirit Airlines
Deal found 11/11$196
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2210:28 pmSJU - ORD
1 stop13h 45mFrontier
Sat 11/295:20 amORD - SJU
1 stop8h 30mFrontier
Deal found 11/12$197
This Cheapflightsfares deal was found by Cheapflights users on 11/12. 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 12/48:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 12/87:10 amORD - SJU
1 stop15h 35mSpirit Airlines
Deal found 11/12$198
This CheapOair deal was found by Cheapflights users on 11/12. 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 12/58:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 12/83:26 pmORD - SJU
1 stop7h 19mSpirit Airlines
Deal found 11/12$199
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/183:54 amSJU - ORD
1 stop15h 06mMultiple Airlines
Sat 1/104:46 pmORD - SJU
1 stop29h 45mMultiple Airlines
Deal found 11/11$202

Cheap flight deals from Caribbean to O'Hare Intl

Keep the following information in mind while searching for Caribbean to O'Hare Intl flight deals. Data was last updated November 13, 2025.

Round-trip from

$183
(Orbitz)

One-way from

$107
(Super.com)

Popular in

December

Cheapest in

January

Average price

$337

Good round-trip deal

$212 or less

Good one-way deal

$179 or less
From Caribbean to Chicago O'Hare Intl
Search Deals
One-way flight from Caribbean to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Caribbean to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Caribbean to Chicago O'Hare Intl.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean 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 November 13, 2025.
Use the filters below to find and compare flights from Caribbean to Chicago O'Hare Intl Airport that are best for you.

Fly from

Caribbean

Fly to

O'Hare Intl

Route

Depart

Return

Price

Santiago de los CaballerosChicago

STI - ORD

STIORD

Santiago de los Caballeros

Sat 12/6

1:01 pm-12:09 am

1 stop13h 08m

Chicago O'Hare Intl

Wed 12/10

3:26 pm-2:42 am

1 stop9h 16m

$235

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 5/9

5:47 am-9:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 5/16

11:27 am-5:12 pm

Nonstop4h 45m

$240

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 12/3

5:20 pm-6:23 pm

1 stop27h 03m

Chicago O'Hare Intl

Wed 12/10

8:45 am-5:25 pm

1 stop6h 40m

$276

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 2/19

2:55 pm-6:08 pm

Nonstop5h 13m

Chicago O'Hare Intl

Mon 2/23

9:30 am-4:02 pm

Nonstop4h 32m

$278

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 12/25

8:10 am-11:32 am

Nonstop5h 22m

Chicago O'Hare Intl

Sun 1/4

2:20 pm-9:00 pm

Nonstop4h 40m

$299

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 12/5

2:55 pm-6:08 pm

Nonstop5h 13m

Chicago O'Hare Intl

Fri 12/12

6:15 pm-5:25 pm

1 stop21h 10m

$305

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Mon 12/8

5:20 pm-8:57 am

1 stop17h 37m

Chicago O'Hare Intl

Mon 12/15

8:45 am-5:25 pm

1 stop6h 40m

$306

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 12/4

5:20 pm-7:42 am

1 stop16h 22m

Chicago O'Hare Intl

Thu 12/11

2:39 pm-5:25 pm

1 stop24h 46m

$306

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 12/12

2:30 pm-6:17 pm

Nonstop4h 47m

Chicago O'Hare Intl

Fri 1/2

9:58 am-3:11 pm

Nonstop4h 13m

$328

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 11/24

3:13 pm-6:54 pm

Nonstop4h 41m

Chicago O'Hare Intl

Sun 11/30

10:15 am-3:28 pm

Nonstop4h 13m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

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

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

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

Currently, January is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $116). Flying from Caribbean to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $193). 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 CB to ORD?

Find hourly flight availability from Caribbean 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 November 13, 2025.

A simple way to save on the total cost of your ticket is to fly from Caribbean to Chicago O'Hare Intl Airport in the morning. If you’re flexible enough to do this you can expect to save up to 14% on your trip compared to booking a flight in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Caribbean to O'Hare Intl. Price data was last updated on December 1, 2024.

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

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

Explore weekly flight availability from Caribbean 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 November 13, 2025.

The most flights from 0CB to ORD are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 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 November 13, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Caribbean to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,007 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,007 reviews
Delta
7.9
Good
8,007 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,015 reviews
Delta
7.9
Good
8,007 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,050 reviews
Delta
7.9
Good
8,007 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,139 reviews
Delta
7.9
Good
8,007 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.8
Fair
3,114 reviews
Delta
7.9
Good
8,007 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Caribbean 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 to Chicago O'Hare Intl Airport?

    Airlines like Spirit Airlines, Arajet, and United Airlines fly from Caribbean to Chicago O'Hare Intl Airport in about 5h 10m. The time it takes to get you to your destination can typically vary by up to 21h 53m. There are 1982 mi between Caribbean and Chicago O'Hare Intl Airport. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Caribbean to Chicago O'Hare Intl Airport one-way?

    The cheapest airlines for a one-way flight from Caribbean to Chicago O'Hare Intl Airport are United Airlines ($108), Spirit Airlines ($124), and Frontier ($174).

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

    While some choose either San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl or Oranjestad Reina Beatrix - Chicago O'Hare Intl, Punta Cana - Chicago O'Hare Intl is the most popular route from Caribbean to Chicago O'Hare Intl Airport.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Caribbean to Chicago O'Hare Intl Airport on time: Spirit Airlines (100%), Air Canada (78%), United Airlines (78%).

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

    Looking for the cheapest flight from Caribbean to Chicago O'Hare Intl Airport? While on average our users pay $625, our data indicates the cheapest price to be $108. The most popular route (Punta Cana - Chicago O'Hare Intl), is priced around $227.

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $116). Flying from Caribbean to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $193). 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
Beloit
Delavan
Elgin
Oak Brook
Elk Grove Village
Downers Grove
Rockford
Naperville
Orland Park
Bridgeview
Warrenville
Waukegan
Aurora
Racine

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Alternative routes for Caribbean to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
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Atlanta to O'Hare Intl flights
John F Kennedy Intl to Midway flights
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LaGuardia to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Punta Cana to O'Hare Intl flights
Hobby to Midway flights
Hobby to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Atlanta to Midway flights
Fort Lauderdale to O'Hare Intl flights
Baltimore to Midway flights
Dulles Intl to Midway flights
Mexico City to O'Hare Intl flights
Love Field to O'Hare Intl flights
Los Angeles to Midway flights
Orlando to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Punta Cana to Midway flights
Charlotte to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Denver to Midway flights
Minneapolis to Midway flights
Raleigh to O'Hare Intl flights
Hartford to O'Hare Intl flights
San Diego to O'Hare Intl flights
Philadelphia to Midway flights
Reagan-National to Midway flights
Tampa to O'Hare Intl flights
Austin to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Orlando to Midway flights
Boston to Midway flights
Portland to O'Hare Intl flights
San Francisco to Midway flights

Top 6 airlines flying from Caribbean to O'Hare Intl

Discover the top 6 airlines that operate flights from Caribbean 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$137Average$335FlexibilityNo cancel feeOn-time65%
FrontierCheapest$139Average$335FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$569FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$269Average$520FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$334Average$576FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$384Average$467FlexibilityNo cancel feeOn-time63%

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