O'Hare Intl

$115+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
ago. 26 — sep. 21
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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 agosto 21, 2025.

Round-trip from

$218
(FlightHub)

One-way from

$115
(FlightHub)
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 agosto 21, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/19. 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.
jue. 8/287:40 pmSJU - ORD
Nonstop5h 03mSpirit Airlines
dom. 8/315:05 amORD - SJU
1 stop15h 43mSpirit Airlines
Deal found 8/19$220
This SmartFares deal was found by Cheapflights users on 8/21. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/2910:16 pmSJU - ORD
1 stop12h 01mSpirit Airlines
dom. 8/315:05 amORD - SJU
1 stop15h 43mSpirit Airlines
Deal found 8/21$221
This Priceline deal was found by Cheapflights users on 8/20. 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.
vie. 9/57:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
mar. 9/166:30 amORD - SJU
1 stop13h 26mSpirit Airlines
Deal found 8/20$227
This Priceline deal was found by Cheapflights users on 8/19. 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.
mié. 9/103:19 pmPUJ - ORD
1 stop8h 29mSpirit Airlines
mar. 9/165:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
Deal found 8/19$230
This SmartFares deal was found by Cheapflights users on 8/20. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/117:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
mar. 9/165:05 amORD - SJU
2 stops32h 06mSpirit Airlines
Deal found 8/20$230
This TravelUp deal was found by Cheapflights users on 8/20. 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 TravelUp is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/19:00 amSJU - ORD
1 stop29h 45mFrontier
lun. 11/35:11 amORD - SJU
1 stop8h 08mFrontier
Deal found 8/20$232
This Priceline deal was found by Cheapflights users on 8/20. 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.
jue. 9/412:28 amSJU - ORD
1 stop12h 30mMultiple Airlines
mar. 9/166:30 amORD - SJU
1 stop13h 26mMultiple Airlines
Deal found 8/20$237
This Mytrip deal was found by Cheapflights users on 8/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/263:39 amSJU - ORD
1 stop12h 38mFrontier
sáb. 10/258:40 amORD - SJU
1 stop9h 18mFrontier
Deal found 8/21$238
This Priceline deal was found by Cheapflights users on 8/19. 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.
lun. 11/103:59 amSJU - ORD
1 stop13h 09mFrontier
sáb. 11/156:00 amORD - SJU
1 stop7h 19mFrontier
Deal found 8/19$239
This Cheapflightsfares deal was found by Cheapflights users on 8/21. 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.
jue. 10/211:59 amSJU - ORD
1 stop6h 40mSpirit Airlines
dom. 10/53:22 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Deal found 8/21$241
This OneTravel deal was found by Cheapflights users on 8/19. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/1811:59 amSJU - ORD
1 stop11h 49mSpirit Airlines
dom. 9/216:10 amORD - SJU
1 stop17h 33mSpirit Airlines
Deal found 8/19$242
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
jue. 9/183:32 amBQN - ORD
1 stop17h 12mFrontier
jue. 10/28:49 pmORD - BQN
1 stop28h 38mFrontier
Deal found 8/20$244

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 agosto 21, 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

vie. 9/5

7:40 pm-11:56 pm

Nonstop5h 16m

Chicago O'Hare Intl

mar. 9/16

6:30 am-8:56 pm

1 stop13h 26m

$227

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mié. 9/10

3:19 pm-10:48 pm

1 stop8h 29m

Chicago O'Hare Intl

mar. 9/16

5:05 am-2:14 pm

1 stop8h 09m

$230

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 9/5

7:15 am-3:50 pm

1 stop9h 35m

Chicago O'Hare Intl

mar. 9/16

6:30 am-8:56 pm

1 stop13h 26m

$237

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mar. 10/21

1:17 pm-3:08 pm

1 stop26h 51m

Chicago O'Hare Intl

sáb. 10/25

8:40 am-6:58 pm

1 stop9h 18m

$238

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 10/2

11:59 am-5:39 pm

1 stop6h 40m

Chicago O'Hare Intl

dom. 10/5

3:22 pm-9:02 pm

Nonstop4h 40m

$241

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

jue. 9/18

3:32 am-7:44 pm

1 stop17h 12m

Chicago O'Hare Intl

jue. 10/2

8:49 pm-2:27 am

1 stop28h 38m

$244

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

vie. 9/19

3:32 am-3:17 pm

1 stop12h 45m

Chicago O'Hare Intl

jue. 10/2

8:49 pm-2:27 am

1 stop28h 38m

$245

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mié. 9/17

6:44 am-4:12 pm

1 stop10h 28m

Chicago O'Hare Intl

dom. 9/21

12:55 pm-6:34 pm

Nonstop4h 39m

$245

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 10/30

7:30 am-1:59 pm

1 stop7h 29m

Chicago O'Hare Intl

sáb. 11/1

6:40 am-5:54 pm

1 stop10h 14m

$245

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mié. 10/8

1:17 pm-8:14 am

1 stop19h 57m

Chicago O'Hare Intl

sáb. 10/11

8:40 am-6:58 pm

1 stop9h 18m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/21

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 agosto 21, 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 agosto 21, 2025.

The most flights from zzEPX to ORD are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 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 agosto 21, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American 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

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
8.0
Very good
8.0
Very good

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
8.0
Very good

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
8.0
Very good

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
8.0
Very good

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
8.0
Very good

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

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.
  • How long is the flight from Caribbean Islands to Chicago O'Hare Intl Airport?

    Spirit Airlines, Frontier, and JetBlue can get you from Caribbean Islands to Chicago O'Hare Intl Airport in just under 5h 16m. Your travel time can differ by up to 21h 35m. The distance from Caribbean Islands to Chicago O'Hare Intl Airport is about 2073 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 (91%), Air Canada (88%) or United Airlines (88%) 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 $587, our data shows the cheapest flight currently is $127. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $228 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 Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Hoffman Estates
Beloit
Skokie
Des Plaines
Elgin
Gurnee
Arlington Heights
Racine
Rockford
Great Lakes
Orland Park
Naperville
Merrillville
Elk Grove Village
Downers Grove
Evanston
Lake Geneva
Joliet

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 agosto 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$136Average$295FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$348FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$440FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$219Average$576FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$431FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$332Average$519FlexibilityNo cancel feeOn-time71%

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