O'Hare Intl

$68+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jan 26 — Feb 21
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Cheap flight deals from Caribbean to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Caribbean (0CB) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$136
(Mytrip)

One-way from

$70
(eDestinos)

Good round-trip deal

$309 or less

Good one-way deal

$188 or less
From Caribbean to Chicago O'Hare Intl
One-way flight from Caribbean to Chicago O'Hare Intl
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.

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 January 21, 2025.

This eDestinos deal was found by Cheapflights users on 1/21. 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 2/207:57 pmSJU - ORD
Nonstop5h 23mSpirit Airlines
Mon 2/2412:55 pmORD - SJU
Nonstop4h 31mSpirit Airlines
Deal found 1/21$136
This Priceline deal was found by Cheapflights users on 1/21. 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 2/276:35 amSJU - ORD
1 stop8h 45mFrontier
Tue 3/43:14 pmORD - SJU
1 stop16h 35mFrontier
Deal found 1/21$140
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/218:31 pmSJU - ORD
Nonstop5h 24mMultiple Airlines
Mon 2/247:08 pmORD - SJU
1 stop12h 41mMultiple Airlines
Deal found 1/21$142
This United Airlines deal was found by Cheapflights users on 1/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/52:05 amSJU - ORD
1 stop9h 35mUnited Airlines
Sun 2/98:50 amORD - SJU
1 stop10h 38mUnited Airlines
Deal found 1/21$245
This eDestinos deal was found by Cheapflights users on 1/20. 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 1/306:19 pmSDQ - ORD
1 stop7h 13mSpirit Airlines
Thu 2/66:55 amORD - SDQ
1 stop8h 19mSpirit Airlines
Deal found 1/20$246
This Priceline deal was found by Cheapflights users on 1/20. 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.
Tue 3/42:48 pmMBJ - ORD
1 stop8h 15mSpirit Airlines
Tue 3/115:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
Deal found 1/20$248
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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 1/306:54 pmPUJ - ORD
Nonstop5h 17mFrontier
Tue 2/46:10 amORD - PUJ
Nonstop4h 50mFrontier
Deal found 1/21$251
This eDestinos deal was found by Cheapflights users on 1/21. 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 2/134:48 pmPUJ - ORD
1 stop9h 10mSpirit Airlines
Sun 2/167:13 pmORD - PUJ
1 stop15h 29mSpirit Airlines
Deal found 1/21$319
This Priceline deal was found by Cheapflights users on 1/21. 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 5/145:08 pmPUJ - ORD
Nonstop5h 06mMultiple Airlines
Wed 5/215:05 amORD - PUJ
1 stop9h 03mMultiple Airlines
Deal found 1/21$328
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 1/302:46 pmSDQ - ORD
1 stop12h 05mMultiple Airlines
Thu 2/66:55 amORD - SDQ
1 stop8h 19mMultiple Airlines
Deal found 1/20$342
This eDestinos deal was found by Cheapflights users on 1/21. 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 5/18:00 amSDQ - ORD
2 stops28h 53mFrontier
Fri 5/96:17 amORD - SDQ
2 stops27h 46mFrontier
Deal found 1/21$370
This Booking.com deal was found by Cheapflights users on 1/20. 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 3/64:50 pmAUA - ORD
1 stop9h 17mSpirit Airlines
Wed 3/127:42 pmORD - AUA
1 stop18h 03mSpirit Airlines
Deal found 1/20$388

Find flights from Caribbean to O'Hare Intl within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/20

7:57 pm-11:20 pm

Nonstop5h 23m

Chicago O'Hare Intl

Mon 2/24

12:55 pm-7:26 pm

Nonstop4h 31m

$136

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/27

6:35 am-1:20 pm

1 stop8h 45m

Chicago O'Hare Intl

Tue 3/4

3:14 pm-9:49 am

1 stop16h 35m

$140

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 2/21

8:31 pm-11:55 pm

Nonstop5h 24m

Chicago O'Hare Intl

Mon 2/24

7:08 pm-9:49 am

1 stop12h 41m

$142

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 2/5

2:05 am-9:40 am

1 stop9h 35m

Chicago O'Hare Intl

Sun 2/9

8:50 am-9:28 pm

1 stop10h 38m

$245

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/4

2:48 pm-10:03 pm

1 stop8h 15m

Chicago O'Hare Intl

Tue 3/11

5:10 am-11:02 am

1 stop5h 52m

$248

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 5/14

5:08 pm-9:14 pm

Nonstop5h 06m

Chicago O'Hare Intl

Wed 5/21

6:20 am-11:55 am

Nonstop4h 35m

$274

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 2/13

4:48 pm-11:58 pm

1 stop9h 10m

Chicago O'Hare Intl

Wed 2/19

5:00 am-3:43 pm

1 stop8h 43m

$275

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 5/14

5:08 pm-9:14 pm

Nonstop5h 06m

Chicago O'Hare Intl

Wed 5/21

5:05 am-3:08 pm

1 stop9h 03m

$328

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 2/13

2:20 pm-11:20 pm

1 stop11h 00m

Chicago O'Hare Intl

Wed 2/19

3:14 pm-3:26 pm

1 stop22h 12m

$357

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 2/27

4:31 pm-10:03 pm

1 stop7h 32m

Chicago O'Hare Intl

Sun 3/2

7:10 am-3:26 pm

1 stop6h 16m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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.

Travel insights for flights from Caribbean to O'Hare Intl

Get recent, data-driven insights about flights from Caribbean to O'Hare Intl including ideal travel times, pricing trends, and more.

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 $320). 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 January 21, 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 January 21, 2025.

The most flights from 0CB to ORD are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 January 21, 2025.
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,662 reviews
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,521 reviews
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.7
Good
1,662 reviews
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.5
Good
1,849 reviews
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.5
Good
1,858 reviews
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.
  • 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 ($70), Frontier ($73), and United Airlines ($152).

  • 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: Spirit Airlines (85%), Air Canada (83%), United Airlines (83%).

  • 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 $815, our data indicates the cheapest price to be $109. The most popular route (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), is priced around $132.

  • 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 $320). 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 Caribbean?

Book flights to Caribbean if you plan to visit one of these locations
Naperville
Rosemont
Beloit
Racine
Hoffman Estates
Schaumburg
Rockford
Skokie
Tinley Park
Arlington Heights
Northbrook
Evanston
Des Plaines
Orland Park
Merrillville
Kenosha
Lake Geneva
New Buffalo
Gurnee
Willowbrook

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 8 airlines flying from Caribbean to O'Hare Intl

Discover the top 8 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$140Average$344FlexibilityNo cancel feeOn-time65%
FrontierCheapest$146Average$305FlexibilityNo cancel feeOn-time62%
DeltaCheapest$187Average$445FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$196Average$556FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$389FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$274Average$460FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$329Average$578FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$521FlexibilityNo cancel feeOn-time70%
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