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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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
1 adult, Economy
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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 September 25, 2025.

Round-trip from

$177
(Cheapflightsfares)

One-way from

$107
(Mytrip)

Popular in

June

Cheapest in

January

Average price

$297

Good round-trip deal

$171 or less

Good one-way deal

$173 or less
From Caribbean to Chicago O'Hare Intl
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One-way flight from Caribbean to Chicago O'Hare Intl
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Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Caribbean to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Caribbean to Chicago O'Hare Intl.
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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 September 25, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 10/253:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Fri 10/319:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/23$177
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 10/249:06 pmSJU - ORD
1 stop12h 12mMultiple Airlines
Mon 10/279:06 pmORD - SJU
Nonstop4h 45mMultiple Airlines
Deal found 9/23$182
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 10/216:22 amSJU - ORD
1 stop31h 23mMultiple Airlines
Sat 10/253:00 pmORD - SJU
Nonstop4h 40mMultiple Airlines
Deal found 9/24$186
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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 10/253:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Sat 11/12:03 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Deal found 9/24$187
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 10/177:43 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Sun 10/197:43 pmORD - SJU
1 stop18h 33mMultiple Airlines
Deal found 9/23$189
This Flightnetwork deal was found by Cheapflights users on 9/25. 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.
Fri 10/177:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Fri 10/247:51 pmORD - SJU
1 stop17h 21mSpirit Airlines
Deal found 9/25$190
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 10/247:43 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Fri 10/315:25 amORD - SJU
1 stop19h 29mMultiple Airlines
Deal found 9/24$192
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 10/107:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sat 10/183:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Deal found 9/23$199
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 10/164:04 pmSJU - ORD
1 stop9h 22mMultiple Airlines
Mon 10/209:06 pmORD - SJU
Nonstop4h 45mMultiple Airlines
Deal found 9/23$200
This Booking.com deal was found by Cheapflights users on 9/25. 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.
Thu 10/161:59 amSJU - ORD
1 stop16h 35mMultiple Airlines
Fri 10/249:06 pmORD - SJU
Nonstop4h 45mMultiple Airlines
Deal found 9/25$204
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 9/23$205
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 10/242:59 amBQN - ORD
1 stop19h 34mMultiple Airlines
Wed 10/295:28 pmORD - BQN
1 stop7h 49mMultiple Airlines
Deal found 9/23$255

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 September 25, 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

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

3:56 pm-8:03 pm

Nonstop5h 07m

Chicago O'Hare Intl

Wed 10/29

8:55 am-2:40 pm

Nonstop4h 45m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

1:05 am-7:38 am

1 stop7h 33m

Chicago O'Hare Intl

Thu 10/30

8:55 am-2:40 pm

Nonstop4h 45m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 10/24

2:22 pm-8:23 pm

1 stop7h 01m

Chicago O'Hare Intl

Mon 10/27

1:08 pm-11:56 pm

1 stop9h 48m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 11/12

2:05 am-9:48 am

1 stop9h 43m

Chicago O'Hare Intl

Mon 11/17

1:00 pm-10:22 pm

1 stop7h 22m

$227

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Fri 10/24

2:59 am-9:33 pm

1 stop19h 34m

Chicago O'Hare Intl

Wed 10/29

5:28 pm-2:17 am

1 stop7h 49m

$255

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 11/4

4:57 pm-1:03 am

1 stop10h 06m

Chicago O'Hare Intl

Tue 11/11

5:59 pm-12:16 pm

1 stop16h 17m

$289

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 11/12

1:21 pm-9:00 pm

1 stop9h 39m

Chicago O'Hare Intl

Sun 11/16

5:59 pm-12:16 pm

1 stop16h 17m

$290

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 10/24

3:57 pm-11:45 pm

1 stop8h 48m

Chicago O'Hare Intl

Fri 10/31

5:05 am-3:00 pm

1 stop8h 55m

$294

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

8:41 am-5:50 pm

1 stop7h 09m

$295

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 10/24

3:56 pm-8:03 pm

Nonstop5h 07m

Chicago O'Hare Intl

Sun 10/26

2:20 pm-8:00 pm

Nonstop4h 40m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/24

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, August is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $245). Flying from Caribbean 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 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 September 25, 2025.

When flying from Caribbean 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 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 September 25, 2025.

The most flights from 0CB to ORD are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, 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 September 25, 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
8.0
Very good
7,973 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

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
7,973 reviews
Delta
8.0
Very good
7,973 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

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
8,926 reviews
Delta
8.0
Very good
7,973 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

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
10,000 reviews
Delta
8.0
Very good
7,973 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

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
8,045 reviews
Delta
8.0
Very good
7,973 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

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
3,162 reviews
Delta
8.0
Very good
7,973 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

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 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 United Airlines, Delta, and Spirit Airlines fly from Caribbean to Chicago O'Hare Intl Airport in about 5h 07m. The time it takes to get you to your destination can typically vary by up to 4h 59m. There are 2073 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 Spirit Airlines ($129), Southwest ($132), and Frontier ($134).

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

    While some choose either Santo Domingo Las Americas - Chicago O'Hare Intl or Simpson Bay Princess Juliana - Chicago O'Hare Intl, San Juan Luis Munoz Marin Intl - 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 (82%), Air Canada (81%), United Airlines (81%).

  • 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 $519, our data indicates the cheapest price to be $106. The most popular route (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), is priced around $127.

  • 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, August is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $245). Flying from Caribbean 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
Gurnee
Hoffman Estates
Des Plaines
Elgin
Arlington Heights
Orland Park
Beloit
Racine
Rockford
Oak Brook
Elk Grove Village
Downers Grove
Naperville
Merrillville
Bridgeview
Warrenville
Joliet

Browse thousands of different options on Cheapflights for your next trip

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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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Newark to Midway flights
Atlanta to Midway flights
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LaGuardia to Midway flights
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Denver to Midway flights
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Baltimore to Midway flights
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Los Angeles to Midway flights
Dulles Intl to Midway flights
Hobby to O'Hare Intl flights
Burbank to O'Hare Intl flights
San Francisco to Midway flights
Philadelphia to Midway flights
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Boston to Midway flights
Minneapolis to Midway flights
Austin to Midway flights
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San Jose to O'Hare Intl flights
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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 September 25, 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$255Average$579FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$460FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$336Average$585FlexibilityNo cancel feeOn-time71%

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