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$106+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
ago. 3 — ago. 101
dom. 8/3
dom. 8/10
1 adult, Economy
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Cheap 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 julio 29, 2025.

Round-trip from

$213
(FlightHub)

One-way from

$106
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$377

Good round-trip deal

$280 or less

Good one-way deal

$150 or less
From Chicago O'Hare Intl to Caribbean
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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 ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Caribbean.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Caribbean.
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Find 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 julio 29, 2025.

This FlightHub deal was found by Cheapflights users on 7/28. 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.
mar. 8/198:12 pmORD - STT
2 stops16h 36mSpirit Airlines
mar. 8/262:43 pmSTT - ORD
1 stop8h 39mSpirit Airlines
Deal found 7/28$213
This CheapOair deal was found by Cheapflights users on 7/29. 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.
sáb. 8/308:47 pmORD - SJU
1 stop17h 20mMultiple Airlines
vie. 9/53:39 amSJU - ORD
1 stop12h 38mMultiple Airlines
Deal found 7/29$227
This CheapOair deal was found by Cheapflights users on 7/29. 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.
sáb. 9/66:44 pmORD - SJU
1 stop15h 20mSpirit Airlines
sáb. 9/203:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Deal found 7/29$228
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/912:20 pmORD - SJU
1 stop11h 07mFrontier
lun. 8/113:34 amSJU - ORD
1 stop7h 40mFrontier
Deal found 7/27$238
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/85:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
mié. 10/153:19 pmPUJ - ORD
1 stop9h 26mSpirit Airlines
Deal found 7/27$298
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/296:45 amORD - PUJ
Nonstop4h 40mFrontier
mié. 8/65:08 pmPUJ - ORD
Nonstop5h 08mFrontier
Deal found 7/27$301
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/126:45 amORD - PUJ
Nonstop4h 40mMultiple Airlines
mar. 8/1912:40 pmPUJ - ORD
1 stop10h 42mMultiple Airlines
Deal found 7/27$308
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
dom. 11/303:30 amORD - PUJ
Nonstop4h 45mArajet
dom. 12/76:00 pmPUJ - ORD
Nonstop5h 10mArajet
Deal found 7/28$313
This CheapOair deal was found by Cheapflights users on 7/28. 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.
sáb. 10/185:05 amORD - AUA
1 stop8h 33mSpirit Airlines
sáb. 10/253:45 pmAUA - ORD
1 stop9h 00mSpirit Airlines
Deal found 7/28$329
This American Airlines deal was found by Cheapflights users on 7/28. 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.
sáb. 10/48:47 pmORD - PUJ
1 stop13h 55mAmerican Airlines
mar. 10/73:21 pmPUJ - ORD
Nonstop5h 15mAmerican Airlines
Deal found 7/28$333
This CheapOair deal was found by Cheapflights users on 7/28. 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.
sáb. 8/165:01 amORD - AUA
1 stop8h 28mMultiple Airlines
sáb. 8/233:45 pmAUA - ORD
1 stop9h 14mMultiple Airlines
Deal found 7/28$341
This Delta deal was found by Cheapflights users on 7/29. 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.
dom. 11/96:00 amORD - PUJ
1 stop6h 23mDelta
vie. 11/142:03 pmPUJ - ORD
1 stop9h 09mDelta
Deal found 7/29$343

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 julio 29, 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

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

mar. 8/19

8:12 pm-1:48 pm

2 stops16h 36m

Saint Thomas Island Cyril E King

mar. 8/26

2:43 pm-10:22 pm

1 stop8h 39m

$213

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 8/30

8:47 pm-3:07 pm

1 stop17h 20m

San Juan Luis Munoz Marin Intl

vie. 9/5

3:39 am-3:17 pm

1 stop12h 38m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 9/6

6:44 pm-11:04 am

1 stop15h 20m

San Juan Luis Munoz Marin Intl

sáb. 9/13

3:19 pm-9:58 pm

1 stop7h 39m

$228

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 8/9

12:20 pm-12:27 am

1 stop11h 07m

San Juan Luis Munoz Marin Intl

lun. 8/11

3:34 am-10:14 am

1 stop7h 40m

$238

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mié. 10/8

5:05 am-2:14 pm

1 stop8h 09m

Punta Cana

mar. 10/14

3:19 pm-11:45 pm

1 stop9h 26m

$298

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 1/13

4:35 am-11:20 am

Nonstop4h 45m

Punta Cana

dom. 1/18

6:00 pm-9:10 pm

Nonstop5h 10m

$307

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 8/12

6:45 am-12:25 pm

Nonstop4h 40m

Punta Cana

mar. 8/19

12:40 pm-10:22 pm

1 stop10h 42m

$308

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

sáb. 8/9

6:45 am-12:25 pm

Nonstop4h 40m

Punta Cana

mar. 8/12

5:45 pm-9:53 pm

Nonstop5h 08m

$311

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

sáb. 10/18

5:05 am-2:38 pm

1 stop8h 33m

Oranjestad Reina Beatrix

sáb. 10/25

3:45 pm-11:45 pm

1 stop9h 00m

$329

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

sáb. 10/4

8:47 pm-11:42 am

1 stop13h 55m

Punta Cana

mar. 10/7

3:21 pm-7:36 pm

Nonstop5h 15m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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 $254). Flying from Chicago O'Hare Intl Airport to Caribbean in June is currently the most expensive (average of $339). 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 julio 29, 2025.

When flying from Chicago O'Hare Intl Airport to Caribbean, 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 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 julio 29, 2025.

The most flights from ORD to 0CB are scheduled on a Monday (9 on average). You will have fewer flight options on Thursday, 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 julio 29, 2025.
See what other customers who have flown with Southwest, Delta, and Copa 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.
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Copa Airlines
7.5
Good
1,493 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,899 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $106. Users have also found prices from $108 and $155 on Spirit Airlines and United 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 - Montego Bay Sangster Intl or Chicago O'Hare Intl - Punta Cana 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 $575 for a flight from Chicago O'Hare Intl Airport to Caribbean. The cheapest flight overall is $117 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $182.

  • 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 $254). Flying from Chicago O'Hare Intl Airport to Caribbean in June is currently the most expensive (average of $339). 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.

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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 10 airlines flying from O'Hare Intl to Caribbean

Discover the top 10 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 julio 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$372FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$381FlexibilityNo cancel feeOn-time65%
DeltaCheapest$190Average$582FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$193Average$476FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$226Average$653FlexibilityNo cancel feeOn-time69%
ArajetCheapest$235Average$315FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$261Average$481FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$335Average$750FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$346Average$655FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$389Average$482FlexibilityNo cancel feeOn-time63%

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