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$72+ Cheap flights from O'Hare Intl (ORD) to Caribbean

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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Caribbean

Cheapest flights from O'Hare Intl to Caribbean
Explore the most affordable flight options available from O'Hare Intl to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 12, 2025.

This Priceline deal was found by Cheapflights users on 12/10. 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. 12/177:00 amORD - SJU
1 stop9h 53mMultiple Airlines
mié. 12/248:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Deal found 12/10$201
This Frontier deal was found by Cheapflights users on 12/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/3111:23 amORD - SJU
1 stop7h 04mFrontier
jue. 1/154:35 pmSJU - ORD
1 stop8h 09mFrontier
Deal found 12/11$205
This Trip.com deal was found by Cheapflights users on 12/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/137:00 amORD - SJU
1 stop9h 53mMultiple Airlines
jue. 12/185:09 pmSJU - ORD
1 stop17h 43mMultiple Airlines
Deal found 12/10$206
This WAYA deal was found by Cheapflights users on 12/10. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/312:15 pmORD - SJU
1 stop8h 35mMultiple Airlines
vie. 1/95:18 pmSJU - ORD
1 stop8h 28mMultiple Airlines
Deal found 12/10$208
This Trip.com deal was found by Cheapflights users on 12/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/137:00 amORD - SJU
1 stop9h 53mJetBlue
lun. 12/151:45 pmSJU - ORD
1 stop10h 07mJetBlue
Deal found 12/11$215
This Trip.com deal was found by Cheapflights users on 12/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/127:00 amORD - SJU
1 stop9h 52mJetBlue
lun. 12/151:45 pmSJU - ORD
1 stop10h 07mJetBlue
Deal found 12/10$220
This Trip.com deal was found by Cheapflights users on 12/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/137:00 amORD - SJU
1 stop9h 53mJetBlue
dom. 12/141:45 pmSJU - ORD
1 stop10h 07mJetBlue
Deal found 12/11$221
This Priceline deal was found by Cheapflights users on 12/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/1611:25 amORD - SJU
1 stop10h 29mMultiple Airlines
mar. 12/236:25 amSJU - ORD
1 stop7h 40mMultiple Airlines
Deal found 12/11$223
This CheapOair deal was found by Cheapflights users on 12/10. 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.
mié. 12/315:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
jue. 1/151:22 pmSJU - ORD
Nonstop5h 15mSpirit Airlines
Deal found 12/10$224
This Frontier deal was found by Cheapflights users on 12/9. 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.
mar. 12/301:27 pmORD - SJU
1 stop15h 07mFrontier
vie. 1/97:10 amSJU - ORD
1 stop11h 57mFrontier
Deal found 12/9$227
This Trip.com deal was found by Cheapflights users on 12/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/137:00 amORD - SJU
1 stop9h 53mMultiple Airlines
lun. 12/158:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Deal found 12/11$228
This Priceline deal was found by Cheapflights users on 12/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/147:10 amORD - PUJ
Nonstop4h 37mFrontier
dom. 12/216:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Deal found 12/11$270

Find flight deals from O'Hare Intl to Caribbean

Keep the following information in mind while searching for O'Hare Intl to Caribbean flight deals. Data was last updated diciembre 12, 2025.

Round-trip from

$199
(Priceline)

One-way from

$72
(Expedia)

Popular in

December

Cheapest in

April

Average price

$592

Good round-trip deal

$303 or less

Good one-way deal

$153 or less
From Chicago O'Hare Intl to Caribbean
Search Deals
One-way flight from Chicago O'Hare Intl to Caribbean
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Highest demand for flights based on searches. 12% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Caribbean.
Search Deals
Price to beat on a one-way flight from Chicago O'Hare Intl to Caribbean.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Caribbean 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 diciembre 12, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Caribbean that are best for you.

Fly from

O'Hare Intl

Fly to

Caribbean

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

vie. 2/27

12:41 pm-11:44 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

sáb. 3/7

5:10 am-11:58 am

1 stop8h 48m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

dom. 1/18

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

vie. 1/23

11:06 am-7:36 pm

1 stop10h 30m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 6/2

3:15 pm-1:59 am

1 stop9h 44m

San Juan Luis Munoz Marin Intl

mar. 6/9

12:30 pm-7:26 pm

1 stop7h 56m

$214

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 2/21

6:04 am-4:56 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

dom. 3/1

5:10 am-11:48 am

1 stop8h 38m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 1/31

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

lun. 2/2

11:06 am-7:36 pm

1 stop10h 30m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 3/11

12:41 pm-9:31 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

jue. 3/19

1:30 am-10:05 am

1 stop9h 35m

$220

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

vie. 3/20

10:56 am-11:23 pm

1 stop11h 27m

San Juan Luis Munoz Marin Intl

mar. 3/24

1:30 am-10:05 am

1 stop9h 35m

$220

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

lun. 2/9

5:15 am-2:10 pm

1 stop6h 55m

Simpson Bay Princess Juliana

mié. 2/18

3:15 pm-12:18 am

1 stop11h 03m

$231

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 2/28

12:51 pm-11:44 pm

1 stop8h 53m

San Juan Luis Munoz Marin Intl

vie. 3/13

1:30 am-10:05 am

1 stop9h 35m

$237

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

lun. 1/5

7:30 am-4:50 pm

1 stop7h 20m

Punta Cana

sáb. 1/17

5:47 pm-11:46 pm

1 stop7h 59m

$280

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

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

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

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

Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $127). Flying from Chicago O'Hare Intl Airport to Caribbean in December is currently the most expensive (average of $221). 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 ORD to CB?

Find hourly flight availability from O'Hare Intl to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated diciembre 12, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Caribbean at noon. If you’re flexible enough to do this you can expect to save up to 30% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Caribbean. Price data was last updated on December 6, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Caribbean flight should consider departing on Friday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago O'Hare Intl Airport to Caribbean

Explore weekly flight availability from O'Hare Intl to Caribbean. 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 diciembre 12, 2025.

The most flights from ORD to 0CB are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 on average).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated diciembre 12, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Chicago O'Hare Intl Airport to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,008 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,095 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,050 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,179 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.8
Fair
3,084 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Caribbean. 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 Chicago O'Hare Intl Airport to Caribbean?

    For as low as $351, JetBlue can have you in Caribbean from Chicago O'Hare Intl Airport in 4h 32m. The distance between Chicago O'Hare Intl Airport and Caribbean is about 1982 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Caribbean one-way?

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $82. Users have also found prices from $83 and $90 on Frontier and Spirit Airlines, respectively.

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

    Most travelers choose Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago O'Hare Intl - Punta Cana or Chicago O'Hare Intl - Oranjestad Reina Beatrix when deciding on the best route from Chicago O'Hare Intl Airport to Caribbean.

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

    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 Chicago O'Hare Intl Airport to Caribbean on time: American Airlines (79%), Air Canada (77%), United Airlines (77%).

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

    On average you can expect to pay $566 for a flight from Chicago O'Hare Intl Airport to Caribbean. The cheapest flight overall is $109 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $113.

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

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Caribbean.

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

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

    Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $127). Flying from Chicago O'Hare Intl Airport to Caribbean in December is currently the most expensive (average of $221). 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

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Alternative routes for O'Hare Intl to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from O'Hare Intl to Caribbean

Discover the top 9 airlines that operate flights from O'Hare Intl to Caribbean. 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 diciembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$107Average$508FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$377FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$147Average$445FlexibilityNo cancel feeOn-time62%
DeltaCheapest$186Average$597FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$215Average$607FlexibilityNo cancel feeOn-time69%
ArajetCheapest$236Average$334FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$335Average$598FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$345Average$641FlexibilityNo cancel feeOn-time71%

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