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$114+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
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 July 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Tue 8/1812:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Wed 8/267:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 7/23$228
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Wed 9/98:45 am
SJU
-
ORD
1 stop31h 00m
Frontier
Deal found 7/26$230
This Justfly.com deal was found by Cheapflights users on 7/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Thu 8/277:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 7/23$231
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 8/242:25 pm
ORD
-
SJU
1 stop7h 55m
Frontier
Wed 9/27:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 7/24$232
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Mon 8/246:35 am
SJU
-
ORD
1 stop31h 15m
Frontier
Deal found 7/27$233
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Sat 9/512:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Thu 9/101:59 am
SJU
-
ORD
1 stop11h 42m
Frontier
Deal found 7/23$234
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:05 am
ORD
-
SJU
1 stop31h 06m
Frontier
Sun 8/307:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 7/26$235
This Super.com deal was found by Cheapflights users on 7/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Thu 8/207:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 7/26$236
This Frontier deal was found by Cheapflights users on 7/24. 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.
Fri 8/1412:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Tue 8/257:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 7/24$237
This Priceline deal was found by Cheapflights users on 7/22. 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 8/2012:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Fri 8/287:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 7/22$238
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:11 am
ORD
-
SJU
1 stop29h 23m
Frontier
Wed 9/168:45 am
SJU
-
ORD
1 stop31h 00m
Frontier
Deal found 7/26$239
This Super.com deal was found by Cheapflights users on 7/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Sun 8/307:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 7/27$240

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 July 27, 2026.

Round-trip from

$228
(Kiwi.com)

One-way from

$114
(Frontier)

Popular in

December

Cheapest in

August

Average price

$386

Good round-trip deal

$322 or less

Good one-way deal

$133 or less
From Chicago O'Hare Intl to Caribbean
Search Deals
One-way flight from Chicago O'Hare Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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.
Search Deals

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 July 27, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 9/24

5:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Tue 9/29

3:56 pm-8:05 pm

Nonstop5h 09m

$252

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 8/31

6:40 am-4:38 pm

1 stop8h 58m

San Juan Luis Munoz Marin Intl

Sat 9/5

2:31 pm-8:30 pm

1 stop6h 59m

$316

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 9/11

8:55 am-2:44 pm

Nonstop4h 49m

San Juan Luis Munoz Marin Intl

Mon 9/14

1:25 pm-10:15 pm

1 stop9h 50m

$329

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 9/11

8:55 am-2:44 pm

Nonstop4h 49m

San Juan Luis Munoz Marin Intl

Sat 9/19

3:56 pm-8:05 pm

Nonstop5h 09m

$355

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 9/11

8:55 am-2:44 pm

Nonstop4h 49m

San Juan Luis Munoz Marin Intl

Sat 9/12

1:00 am-7:41 am

1 stop7h 41m

$372
Quickest round-trip

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 10/24

12:12 pm-5:57 pm

Nonstop4h 45m

Punta Cana

Sun 11/1

6:10 pm-9:20 pm

Nonstop5h 10m

$375

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 10/11

8:55 am-2:44 pm

Nonstop4h 49m

San Juan Luis Munoz Marin Intl

Sat 10/17

3:56 pm-8:05 pm

Nonstop5h 09m

$391

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 10/16

6:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Thu 10/22

7:30 pm-11:40 pm

Nonstop5h 10m

$395

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 10/5

5:40 pm-12:40 pm

1 stop18h 00m

Punta Cana

Fri 10/16

2:05 pm-2:30 pm

2 stops25h 25m

$395

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 8/20

2:35 pm-11:20 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Tue 8/25

5:00 pm-11:44 pm

1 stop7h 44m

$404

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 60 resultsSorted by cheapest first
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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, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $435). Flying from Chicago O'Hare Intl Airport to Caribbean in December is currently the most expensive (average of $605). 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 July 27, 2026.

A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Caribbean in the evening. If you’re flexible enough to do this you can expect to save up to 33% on your trip compared to booking a flight in the morning.

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 July 27, 2026.

The most flights from ORD to 0CB are scheduled on a Monday (10 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Caribbean?

The price you pay for your flight from Chicago O'Hare Intl Airport to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 48 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 July 25, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Caribbean flight should consider departing on Sunday 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.

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 July 27, 2026.
See what other customers who have flown with United Airlines,American Airlines, andJetBlue 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.
United Airlines
7.4
Good
10,046 reviews

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
United Airlines
7.4
Good
10,046 reviews
United Airlines
7.4
Good
10,046 reviews

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
American Airlines
7.1
Good
11,839 reviews
United Airlines
7.4
Good
10,046 reviews

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
JetBlue
7.1
Good
3,026 reviews
United Airlines
7.4
Good
10,046 reviews

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
Frontier
5.6
Fair
2,756 reviews
United Airlines
7.4
Good
10,046 reviews

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

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 $375, United Airlines can have you in Caribbean from Chicago O'Hare Intl Airport in 4h 45m. 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 $75. Users have also found prices from $86 and $100 on Frontier and Arajet, 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 - Montego Bay Sangster Intl 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: Air Canada (83%), United Airlines (83%), Air New Zealand (83%).

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

    On average you can expect to pay $880 for a flight from Chicago O'Hare Intl Airport to Caribbean. The cheapest flight overall is $74 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $244.

  • 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, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $435). Flying from Chicago O'Hare Intl Airport to Caribbean in December is currently the most expensive (average of $605). 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 July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$118Average$521FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$119Average$440FlexibilityNo cancel feeOn-time62%
FrontierCheapest$144Average$589FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$175Average$528FlexibilityNo cancel feeOn-time67%
ArajetCheapest$218Average$370FlexibilityNo cancel feeOn-timeN/A
Hahn AirCheapest$228Average$486FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$261Average$590FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$302Average$614FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$376Average$568FlexibilityNo cancel feeOn-time63%

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