O'Hare Intl

$112+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Apr 12 — Apr 191
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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 March 13, 2026.

This eDestinos deal was found by Cheapflights users on 3/8. 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.
Fri 5/84:11 pm
SJU
-
ORD
1 stop8h 05m
Frontier
Mon 5/117:15 pm
ORD
-
SJU
1 stop21h 15m
Frontier
Deal found 3/8$183
This Cheapflightsfares deal was found by Cheapflights users on 3/8. 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 4/293:21 am
SJU
-
ORD
1 stop10h 44m
Spirit Airlines
Mon 5/47:50 am
ORD
-
SJU
1 stop17h 16m
Spirit Airlines
Deal found 3/8$193
This Expedia deal was found by Cheapflights users on 3/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/911:01 am
SJU
-
ORD
1 stop13h 35m
Multiple Airlines
Mon 4/1310:55 am
ORD
-
SJU
1 stop12h 03m
Multiple Airlines
Deal found 3/9$200
This eDestinos deal was found by Cheapflights users on 3/11. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:00 am
SJU
-
ORD
1 stop9h 42m
Frontier
Mon 4/1311:59 am
ORD
-
SJU
1 stop10h 54m
Frontier
Deal found 3/11$201
This Frontier deal was found by Cheapflights users on 3/9. 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 5/13:23 pm
SJU
-
ORD
1 stop8h 16m
Frontier
Mon 5/42:10 pm
ORD
-
SJU
1 stop8h 33m
Frontier
Deal found 3/9$202
This Cheapflightsfares deal was found by Cheapflights users on 3/9. 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.
Tue 4/71:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Sun 4/126:10 pm
ORD
-
SJU
1 stop16h 39m
Spirit Airlines
Deal found 3/9$206
This Orbitz deal was found by Cheapflights users on 3/8. 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.
Thu 8/278:10 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Wed 9/27:20 pm
ORD
-
SJU
1 stop9h 33m
Frontier
Deal found 3/8$207
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/176:00 am
SJU
-
ORD
1 stop17h 54m
Frontier
Sun 4/193:08 pm
ORD
-
SJU
1 stop22h 19m
Frontier
Deal found 3/9$209
This Cheapflightsfares deal was found by Cheapflights users on 3/8. 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 4/81:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Mon 4/1310:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/8$213
This CheapOair deal was found by Cheapflights users on 3/9. 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 4/243:23 pm
SJU
-
ORD
1 stop8h 16m
Multiple Airlines
Sun 4/267:50 am
ORD
-
SJU
1 stop16h 08m
Multiple Airlines
Deal found 3/9$215
This Travelocity deal was found by Cheapflights users on 3/9. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/71:29 am
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Sun 4/127:25 am
ORD
-
SJU
1 stop9h 14m
Multiple Airlines
Deal found 3/9$216
This Cheapflightsfares deal was found by Cheapflights users on 3/9. 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 5/133:21 am
SJU
-
ORD
1 stop10h 44m
Spirit Airlines
Mon 5/187:50 am
ORD
-
SJU
1 stop17h 16m
Spirit Airlines
Deal found 3/9$217

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 March 13, 2026.

Round-trip from

$183
(eDestinos)

One-way from

$112
(Priceline)

Popular in

December

Cheapest in

February

Average price

$365

Good round-trip deal

$283 or less

Good one-way deal

$181 or less
From Caribbean to Chicago O'Hare Intl
One-way flight from Caribbean to Chicago O'Hare Intl
Highest demand for flights based on searches. 7% potential increase in price ($22 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Average for round-trip flights in March 2026
Price to beat on a round-trip flight from Caribbean to Chicago O'Hare Intl.
Price to beat on a one-way flight from Caribbean to Chicago O'Hare Intl.

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 March 13, 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

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 5/19

3:20 pm-11:34 pm

1 stop8h 14m

Chicago O'Hare Intl

Mon 8/17

8:30 am-12:31 pm

Nonstop4h 01m

$272

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 5/25

2:55 pm-7:10 am

1 stop16h 15m

Chicago O'Hare Intl

Wed 9/2

8:30 am-12:31 pm

Nonstop4h 01m

$277

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 5/15

2:40 pm-10:20 am

1 stop19h 40m

Chicago O'Hare Intl

Wed 5/27

5:30 am-1:30 pm

1 stop8h 00m

$291

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 4/18

2:40 pm-9:00 am

1 stop18h 20m

Chicago O'Hare Intl

Thu 4/30

9:35 pm-3:10 pm

1 stop17h 35m

$291

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 4/23

1:52 pm-6:15 pm

Nonstop4h 23m

Chicago O'Hare Intl

Thu 4/30

2:25 pm-3:10 pm

1 stop24h 45m

$291

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

2:40 pm-1:27 am

1 stop10h 47m

Chicago O'Hare Intl

Sat 5/30

8:40 am-12:50 pm

Nonstop4h 10m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 5/12

2:40 pm-11:15 pm

1 stop8h 35m

Chicago O'Hare Intl

Thu 5/28

9:40 pm-3:10 pm

1 stop17h 30m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 6/2

4:12 pm-4:52 pm

1 stop24h 40m

Chicago O'Hare Intl

Sat 9/12

6:30 am-1:30 pm

1 stop7h 00m

$292
Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 5/15

1:15 pm-5:55 pm

Nonstop4h 40m

Chicago O'Hare Intl

Wed 5/27

9:20 am-1:30 pm

Nonstop4h 10m

$318

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/7

2:20 pm-12:45 am

1 stop11h 25m

Chicago O'Hare Intl

Mon 5/11

9:30 am-3:12 pm

Nonstop4h 42m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/8

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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, May is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $112). Flying from Caribbean to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $157). 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 March 13, 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 47% on your trip compared to booking a flight at noon.

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 March 12, 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.

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 March 13, 2026.

The most flights from 0CB to ORD are scheduled on a Thursday (12 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 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 March 13, 2026.
Get a feel of what it's like to fly with United Airlines,JetBlue, andAmerican 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.

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

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.

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

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.

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

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.

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

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.

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

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.

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

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 American Airlines, United Airlines, and Southwest fly from Caribbean to Chicago O'Hare Intl Airport in about 8h 14m. The time it takes to get you to your destination can typically vary by up to 11h 26m. There are 1724 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), Spirit Airlines ($94), and Frontier ($102).

  • What are the most popular routes 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: Air Canada (82%), United Airlines (82%), Air New Zealand (82%).

  • 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 $618, our data indicates the cheapest price to be $117. The most popular route (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), is priced around $204.

  • 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, May is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $112). Flying from Caribbean to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $157). 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
Gurnee
Naperville
Lake Geneva
Hoffman Estates
Delavan
Downers Grove
Des Plaines
Elgin
Elk Grove Village
Skokie
Oak Brook
South Holland
Beloit
Libertyville
Waukegan
Warrenville
Bridgeview
Oakbrook Terrace

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.

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 March 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$64Average$335FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$124Average$337FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$131Average$201FlexibilityNo cancel feeOn-time62%
DeltaCheapest$191Average$714FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$256Average$518FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$257Average$530FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$292Average$483FlexibilityNo cancel feeOn-time63%

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