O'Hare Intl

$114+ Cheap flights from Caribbean Islands 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 8/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jul 8 — Jul 151
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Cheap flight deals from Caribbean Islands to O'Hare Intl

Keep the following information in mind while searching for Caribbean Islands to O'Hare Intl flight deals. Data was last updated July 3, 2025.

Round-trip from

$199
(Priceline)

One-way from

$114
(eDestinos)
From Caribbean Islands to Chicago O'Hare Intl
One-way flight from Caribbean Islands to Chicago O'Hare Intl

Find flight deals from Caribbean Islands to O'Hare Intl

Cheapest flights from Caribbean Islands to O'Hare Intl
Explore the most affordable flight options available from Caribbean Islands to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

This Priceline deal was found by Cheapflights users on 6/30. 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.
Fri 7/253:50 pmSJU - ORD
1 stop16h 14mMultiple Airlines
Fri 8/15:01 amORD - SJU
1 stop8h 17mMultiple Airlines
Deal found 6/30$199
This FlightHub deal was found by Cheapflights users on 7/2. 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 9/1812:29 pmSJU - ORD
1 stop11h 19mSpirit Airlines
Wed 9/246:44 pmORD - SJU
1 stop15h 50mSpirit Airlines
Deal found 7/2$209
This Priceline deal was found by Cheapflights users on 6/30. 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 7/2412:59 amSJU - ORD
1 stop19h 28mFrontier
Fri 8/15:01 amORD - SJU
1 stop8h 17mFrontier
Deal found 6/30$217
This FlightHub deal was found by Cheapflights users on 7/1. 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 7/2410:48 amMBJ - ORD
1 stop13h 05mSpirit Airlines
Mon 8/45:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Deal found 7/1$238
This Priceline deal was found by Cheapflights users on 7/1. 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.
Mon 8/112:59 amBQN - ORD
1 stop8h 15mFrontier
Sat 8/169:08 amORD - BQN
1 stop15h 53mFrontier
Deal found 7/1$268
This Expedia deal was found by Cheapflights users on 7/1. 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.
Sat 8/304:05 pmPUJ - ORD
1 stop8h 54mSpirit Airlines
Sat 9/65:05 amORD - PUJ
1 stop8h 23mSpirit Airlines
Deal found 7/1$273
This Priceline deal was found by Cheapflights users on 7/3. 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.
Mon 8/115:08 pmPUJ - ORD
Nonstop5h 08mFrontier
Wed 8/135:01 amORD - PUJ
1 stop8h 09mFrontier
Deal found 7/3$284
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Wed 8/1311:55 amPUJ - ORD
1 stop11h 46mAmerican Airlines
Sun 8/175:20 amORD - PUJ
1 stop9h 30mAmerican Airlines
Deal found 7/1$306
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Mon 8/49:04 pmPUJ - ORD
1 stop20h 07mMultiple Airlines
Mon 8/255:05 amORD - PUJ
1 stop8h 55mMultiple Airlines
Deal found 7/1$324
This Cheapflightsfares deal was found by Cheapflights users on 7/1. 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 8/610:52 amSTX - ORD
1 stop13h 21mSpirit Airlines
Sun 8/105:40 pmORD - STX
1 stop15h 07mSpirit Airlines
Deal found 7/1$326
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Fri 8/12:30 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Sat 8/210:05 pmORD - MBJ
1 stop16h 43mAmerican Airlines
Deal found 7/1$338
This SmartFares deal was found by Cheapflights users on 7/1. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/131:01 pmSDQ - ORD
1 stop10h 21mSpirit Airlines
Mon 8/185:05 amORD - SDQ
1 stop9h 55mSpirit Airlines
Deal found 7/1$348

Cheapflights Fare Finder

Customize your flight search to find flights from Caribbean Islands 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 3, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Chicago O'Hare Intl Airport that are best for you.

Fly from

Caribbean Islands

Fly to

O'Hare Intl

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 7/25

3:50 pm-7:04 am

1 stop16h 14m

Chicago O'Hare Intl

Fri 8/1

5:01 am-2:18 pm

1 stop8h 17m

$199

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 9/18

12:29 pm-10:48 pm

1 stop11h 19m

Chicago O'Hare Intl

Wed 9/24

6:44 pm-11:34 am

1 stop15h 50m

$209

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 7/24

12:59 am-7:27 pm

1 stop19h 28m

Chicago O'Hare Intl

Fri 8/1

5:01 am-2:18 pm

1 stop8h 17m

$217

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 7/24

10:48 am-11:53 pm

1 stop13h 05m

Chicago O'Hare Intl

Mon 8/4

5:05 am-11:05 am

1 stop6h 00m

$238

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Mon 8/11

2:59 am-10:14 am

1 stop8h 15m

Chicago O'Hare Intl

Sat 8/16

9:08 am-2:01 am

1 stop15h 53m

$268

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 8/30

4:05 pm-11:59 pm

1 stop8h 54m

Chicago O'Hare Intl

Sat 9/6

5:05 am-2:28 pm

1 stop8h 23m

$273

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Mon 8/11

5:08 pm-9:16 pm

Nonstop5h 08m

Chicago O'Hare Intl

Wed 8/13

5:01 am-2:10 pm

1 stop8h 09m

$284

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 8/13

11:55 am-10:41 pm

1 stop11h 46m

Chicago O'Hare Intl

Sun 8/17

5:20 am-3:50 pm

1 stop9h 30m

$306

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Mon 8/4

9:04 pm-4:11 pm

1 stop20h 07m

Chicago O'Hare Intl

Mon 8/25

5:05 am-3:00 pm

1 stop8h 55m

$324

ChristianstedChicago

STX - ORD

STXORD

Christiansted Henry Rohlsen

Wed 8/6

10:52 am-11:13 pm

1 stop13h 21m

Chicago O'Hare Intl

Sun 8/10

5:40 pm-9:47 am

1 stop15h 07m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 60 results
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Best time to book a flight from Caribbean Islands to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Caribbean Islands 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 Islands to Chicago O'Hare Intl Airport

What is the cheapest month to book a flight from Caribbean Islands to Chicago O'Hare Intl Airport?

Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Chicago O'Hare Intl Airport (average of $245). Flying from Caribbean Islands 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 EPX to ORD?

Find hourly flight availability from Caribbean Islands 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 3, 2025.

When flying from Caribbean Islands 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 Islands to Chicago O'Hare Intl Airport

Explore weekly flight availability from Caribbean Islands 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 3, 2025.

The most flights from zzEPX to ORD are scheduled on a Wednesday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 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 July 3, 2025.
Get a feel of what it's like to fly with Delta, Copa Airlines, and United Airlines from Caribbean Islands to Chicago O'Hare Intl Airport by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good
8.0
Very good

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands 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 Islands to Chicago O'Hare Intl Airport one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $114. Users have also found prices from $115 and $133 on Arajet and Frontier, respectively.

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

  • What are the most reliable airlines from Caribbean Islands to Chicago O'Hare Intl Airport?

    No one likes to see their flight delayed. When booking a flight from Caribbean Islands to Chicago O'Hare Intl Airport consider choosing Spirit Airlines (97%), Air Canada (89%) or United Airlines (89%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Caribbean Islands to Chicago O'Hare Intl Airport?

    While on average a flight from Caribbean Islands to Chicago O'Hare Intl Airport is generally $671, our data shows the cheapest flight currently is $132. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $209 for that flight.

  • Can I find deals for flights from Caribbean Islands to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Caribbean Islands to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean Islands 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 Islands to O'Hare Intl.

  • Can I find deals for business class flights from Caribbean Islands to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Caribbean Islands 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 Islands to Chicago O'Hare Intl Airport?

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

Book flights to Caribbean Islands if you plan to visit one of these locations
Schaumburg
Hoffman Estates
Rosemont
Beloit
Skokie
Des Plaines
Arlington Heights
Elgin
Naperville
Orland Park
Elk Grove Village
Racine
Rockford
Tinley Park
Merrillville
Bridgeview
Glenview
Lake Geneva
Joliet
Waukegan

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Caribbean Islands to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from Caribbean Islands to O'Hare Intl

Discover the top 6 airlines that operate flights from Caribbean Islands 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$136Average$329FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$327FlexibilityNo cancel feeOn-time62%
DeltaCheapest$172Average$495FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$217Average$527FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$431FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$329Average$558FlexibilityNo cancel feeOn-time71%

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