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O'Hare Intl

$134+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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Cheap 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 July 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/277:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Sat 8/2912:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/22$184
This Frontier deal was found by Cheapflights users on 7/22. 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 8/277:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Sun 8/3012:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/22$185
This Priceline deal was found by Cheapflights users on 7/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Sat 9/512:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/23$188
This eDestinos deal was found by Cheapflights users on 7/26. 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 8/207:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Sat 8/2212:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/26$196
This Orbitz deal was found by Cheapflights users on 7/26. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Sat 9/512:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/26$197
This Frontier deal was found by Cheapflights users on 7/22. 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.
Wed 8/267:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Fri 8/2812:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/22$198
This Booking.com deal was found by Cheapflights users on 7/22. 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 8/267:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Sun 8/3012:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/22$199
This FlightHub deal was found by Cheapflights users on 7/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Fri 8/2812:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/25$200
This Booking.com deal was found by Cheapflights users on 7/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/257:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Tue 9/112:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/23$204
This Trip.com deal was found by Cheapflights users on 7/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Thu 8/2712:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 7/26$208
This deal was found by Cheapflights users on 7/23. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:59 am
SJU
-
ORD
1 stop11h 42m
Frontier
Fri 9/254:49 pm
ORD
-
SJU
1 stop8h 01m
Frontier
Deal found 7/23$211
This eDestinos deal was found by Cheapflights users on 7/22. 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 9/177:30 pm
PUJ
-
ORD
Nonstop5h 10m
Arajet
Fri 12/115:45 am
ORD
-
PUJ
Nonstop4h 45m
Arajet
Deal found 7/22$279

Find 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 July 27, 2026.

Round-trip from

$184
(Kiwi.com)

One-way from

$134
(Trip.com)

Popular in

June

Cheapest in

February

Average price

$340

Good round-trip deal

$299 or less

Good one-way deal

$175 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. 17% potential increase in price ($70 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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.
Search Deals

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 July 27, 2026.
Use the filters below to find and compare flights from Caribbean to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 9/24

7:30 pm-11:40 pm

Nonstop5h 10m

Chicago O'Hare Intl

Thu 10/1

2:00 pm-4:05 pm

2 stops25h 05m

$367

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/29

12:00 pm-8:14 pm

1 stop9h 14m

Chicago O'Hare Intl

Tue 11/3

2:16 pm-9:00 pm

Nonstop4h 44m

$382

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 11/6

6:59 pm-11:52 pm

1 stop6h 53m

Chicago O'Hare Intl

Mon 11/9

8:04 am-5:25 pm

1 stop7h 21m

$386

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 9/3

4:55 pm-11:40 pm

1 stop7h 45m

Chicago O'Hare Intl

Sun 9/6

5:00 am-1:45 pm

1 stop7h 45m

$386

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 12/24

5:45 pm-11:50 pm

1 stop8h 05m

Chicago O'Hare Intl

Sat 1/2

7:10 am-5:05 pm

1 stop7h 55m

$392

NassauChicago

NAS - ORD

NASORD

Nassau Intl

Fri 9/25

6:30 pm-7:48 pm

1 stop26h 18m

Chicago O'Hare Intl

Sun 9/27

8:40 pm-5:30 pm

1 stop19h 50m

$393

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 9/4

2:12 pm-6:55 pm

Nonstop4h 43m

Chicago O'Hare Intl

Fri 9/11

5:48 pm-11:17 am

1 stop17h 29m

$396

NassauChicago

NAS - ORD

NASORD

Nassau Intl

Thu 9/10

6:30 pm-10:15 am

2 stops16h 45m

Chicago O'Hare Intl

Sun 9/13

9:50 am-5:30 pm

1 stop6h 40m

$397

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 9/17

4:50 pm-7:56 am

2 stops15h 06m

Chicago O'Hare Intl

Tue 9/22

5:30 am-11:48 am

1 stop6h 18m

$397

NassauChicago

NAS - ORD

NASORD

Nassau Intl

Sat 10/3

6:30 pm-9:00 am

1 stop15h 30m

Chicago O'Hare Intl

Sat 10/10

9:50 am-5:30 pm

1 stop6h 40m

$405

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 60 resultsSorted by cheapest first
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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, February is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $257). Flying from Caribbean to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $461). 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 July 27, 2026.

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 evening. If you’re flexible enough to do this you can expect to save up to 35% on your trip compared to booking a flight in the afternoon.

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 July 27, 2026.

The most flights from 0CB to ORD are scheduled on a Monday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 on average).

How far ahead should I book a flight from Caribbean to Chicago O'Hare Intl Airport?

The best time to book flights from Caribbean to Chicago O'Hare Intl Airport is 81 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 July 25, 2026.

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

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 July 27, 2026.
Get a feel of what it's like to fly with United Airlines,American Airlines, andJetBlue 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.
United Airlines
7.4
Good
10,045 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
10,045 reviews
United Airlines
7.4
Good
10,045 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,837 reviews
United Airlines
7.4
Good
10,045 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
JetBlue
7.1
Good
3,026 reviews
United Airlines
7.4
Good
10,045 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Frontier
5.6
Fair
2,754 reviews
United Airlines
7.4
Good
10,045 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 Air Canada fly from Caribbean to Chicago O'Hare Intl Airport in about 6h 53m. The time it takes to get you to your destination can typically vary by up to 19h 25m. 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 JetBlue ($74), Frontier ($94), and Arajet ($121).

  • 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 Punta Cana - 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: American Airlines (87%), Alaska Airlines (87%), Air Canada (84%).

  • 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 $653, our data indicates the cheapest price to be $103. The most popular route (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), is priced around $239.

  • 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, February is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $257). Flying from Caribbean to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $461). 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
Benton Harbor
Rosemont
Schaumburg
Lake Geneva
Naperville
Oak Brook
Delavan
Oakbrook Terrace
Gurnee
South Holland
Libertyville
Orland Park
Hoffman Estates
Beloit
Downers Grove
Rockford
Racine
Great Lakes
Janesville
Joliet

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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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Mexico City to O'Hare Intl flights
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Atlanta to Midway flights
John F Kennedy Intl to Midway flights
LaGuardia to Midway flights
Miami to O'Hare Intl flights
Dulles Intl to Midway flights
San Diego to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Portland to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
San Francisco to Midway flights
Baltimore to Midway flights
Reagan-National to Midway flights
Los Angeles to Midway flights
Hobby to Midway flights
Mexico City to Midway flights
Hartford to O'Hare Intl flights
Las Vegas to O'Hare Intl flights
Minneapolis to Midway flights
Salt Lake City to O'Hare Intl flights
Sacramento to O'Hare Intl flights
San Jose to O'Hare Intl flights
George Bush Intcntl to Midway flights
Frederic Chopin to O'Hare Intl flights

Top 7 airlines flying from Caribbean to O'Hare Intl

Discover the top 7 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 July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$112Average$418FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$128Average$281FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$131Average$293FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$227Average$516FlexibilityNo cancel feeOn-time71%
ArajetCheapest$237Average$445FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$267Average$482FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$292Average$427FlexibilityNo cancel feeOn-time63%

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