O'Hare Intl

$90+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Apr 2 — Apr 91
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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 March 28, 2025.

Round-trip from

$175
(Cheapflightsfares)

One-way from

$90
(eDestinos)

Popular in

March

Cheapest in

January

Average price

$353

Good round-trip deal

$328 or less

Good one-way deal

$177 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. 9% potential increase in price ($30 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Average for round-trip flights in March 2025
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 March 28, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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.
Fri 4/256:35 amSJU - ORD
Nonstop5h 23mSpirit Airlines
Tue 4/297:00 pmORD - SJU
1 stop12h 26mSpirit Airlines
Deal found 3/27$159
This CheapOair deal was found by Cheapflights users on 3/27. 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.
Thu 5/15:54 pmPUJ - ORD
Nonstop5h 06mFrontier
Mon 5/56:10 amORD - PUJ
Nonstop4h 41mFrontier
Deal found 3/27$236
This JetBlue deal was found by Cheapflights users on 3/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/77:01 amSJU - ORD
1 stop9h 03mJetBlue
Mon 5/128:45 amORD - SJU
1 stop8h 20mJetBlue
Deal found 3/26$265
This Cheapflightsfares deal was found by Cheapflights users on 3/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2611:05 amSTT - ORD
1 stop14h 53mSpirit Airlines
Wed 4/307:47 pmORD - STT
1 stop13h 13mSpirit Airlines
Deal found 3/26$273
This CheapOair deal was found by Cheapflights users on 3/27. 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.
Thu 5/812:42 pmPUJ - ORD
1 stop11h 47mMultiple Airlines
Sun 5/116:10 amORD - PUJ
Nonstop4h 41mMultiple Airlines
Deal found 3/27$286
This American Airlines deal was found by Cheapflights users on 3/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/111:40 amPUJ - ORD
1 stop13h 09mAmerican Airlines
Mon 5/57:16 pmORD - PUJ
1 stop17h 19mAmerican Airlines
Deal found 3/27$289
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 4/166:21 amSJU - ORD
1 stop7h 41mMultiple Airlines
Tue 4/228:04 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 3/27$290
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/312:00 pmMBJ - ORD
1 stop12h 58mSpirit Airlines
Wed 5/75:05 amORD - MBJ
1 stop5h 57mSpirit Airlines
Deal found 3/25$291
This Frontier deal was found by Cheapflights users on 3/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/82:55 amSJU - ORD
1 stop8h 45mFrontier
Mon 4/145:19 pmORD - SJU
1 stop6h 35mFrontier
Deal found 3/26$296
This eDestinos deal was found by Cheapflights users on 3/27. 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.
Wed 4/93:18 pmPUJ - ORD
1 stop10h 02mSpirit Airlines
Wed 4/305:36 amORD - PUJ
1 stop7h 37mSpirit Airlines
Deal found 3/27$302
This Cheapflightsfares deal was found by Cheapflights users on 3/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/91:39 pmKIN - ORD
1 stop10h 41mSpirit Airlines
Tue 4/155:36 amORD - KIN
1 stop6h 55mSpirit Airlines
Deal found 3/26$314
This Delta deal was found by Cheapflights users on 3/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/221:55 pmSJU - ORD
1 stop7h 26mDelta
Sat 6/1411:18 amORD - SJU
1 stop10h 33mDelta
Deal found 3/26$341

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 28, 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

Fri 4/25

6:35 am-10:58 am

Nonstop5h 23m

Chicago O'Hare Intl

Tue 4/29

7:00 pm-8:26 am

1 stop12h 26m

$159

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 5/2

5:08 pm-9:11 pm

Nonstop5h 03m

Chicago O'Hare Intl

Mon 5/12

6:10 am-11:51 am

Nonstop4h 41m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 5/7

7:01 am-3:04 pm

1 stop9h 03m

Chicago O'Hare Intl

Mon 5/12

8:45 am-6:05 pm

1 stop8h 20m

$265

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Sat 4/26

11:05 am-12:58 am

1 stop14h 53m

Chicago O'Hare Intl

Wed 4/30

7:47 pm-10:00 am

1 stop13h 13m

$273

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/8

12:42 pm-11:29 pm

1 stop11h 47m

Chicago O'Hare Intl

Sun 5/11

6:10 am-11:51 am

Nonstop4h 41m

$286

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/1

11:40 am-11:49 pm

1 stop13h 09m

Chicago O'Hare Intl

Mon 5/5

7:16 pm-1:35 pm

1 stop17h 19m

$289

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 4/16

6:21 am-1:02 pm

1 stop7h 41m

Chicago O'Hare Intl

Tue 4/22

8:04 am-1:45 pm

Nonstop4h 41m

$290

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/3

12:00 pm-12:58 am

1 stop12h 58m

Chicago O'Hare Intl

Wed 5/7

5:05 am-11:02 am

1 stop5h 57m

$291

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 4/8

2:55 am-10:40 am

1 stop8h 45m

Chicago O'Hare Intl

Mon 4/14

5:19 pm-12:54 am

1 stop6h 35m

$296

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 4/9

3:18 pm-12:20 am

1 stop10h 02m

Chicago O'Hare Intl

Wed 4/30

5:36 am-2:13 pm

1 stop7h 37m

$302

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

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 $323). 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 28, 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 March 28, 2025.

The most flights from 0CB to ORD are scheduled on a Thursday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 March 28, 2025.

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
8.0
Very good

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 ($90), Frontier ($135), and JetBlue ($141).

  • 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 (95%), Air Canada (94%), United Airlines (94%).

  • 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 $480, our data indicates the cheapest price to be $99. The most popular route (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), is priced around $192.

  • 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 $323). 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
Rosemont
Beloit
Naperville
Schaumburg
Racine
Hoffman Estates
Rockford
Tinley Park
Skokie
Kenosha
Arlington Heights
Joliet
Orland Park
Merrillville
Northbrook
Evanston
New Buffalo
Elgin
Glenview
Lake Geneva

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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$283FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$283FlexibilityNo cancel feeOn-time65%
DeltaCheapest$172Average$492FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$214Average$574FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$403FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$308Average$567FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$483FlexibilityNo cancel feeOn-time70%
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