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$76+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
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 March 26, 2025.

Round-trip from

$197
(CheapOair)

One-way from

$76
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$430

Good round-trip deal

$266 or less

Good one-way deal

$151 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. 16% potential increase in price ($70 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 26, 2025.

This CheapOair deal was found by Cheapflights users on 3/25. 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.
Tue 4/227:00 pmORD - SJU
1 stop12h 26mSpirit Airlines
Mon 4/2812:54 amSJU - ORD
1 stop8h 41mSpirit Airlines
Deal found 3/25$197
This CheapOair deal was found by Cheapflights users on 3/25. 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.
Sat 4/56:09 pmORD - SJU
1 stop14h 17mMultiple Airlines
Tue 4/82:55 amSJU - ORD
1 stop8h 45mMultiple Airlines
Deal found 3/25$253
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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.
Sun 4/277:33 pmORD - STT
1 stop13h 27mSpirit Airlines
Sat 5/102:41 pmSTT - ORD
1 stop9h 48mSpirit Airlines
Deal found 3/25$260
This Frontier deal was found by Cheapflights users on 3/25. 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.
Mon 4/79:50 amORD - SJU
1 stop7h 38mFrontier
Tue 4/82:55 amSJU - ORD
1 stop8h 45mFrontier
Deal found 3/25$296
This United Airlines deal was found by Cheapflights users on 3/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/16:03 pmORD - SJU
Nonstop4h 51mUnited Airlines
Tue 6/31:05 amSJU - ORD
1 stop8h 34mUnited Airlines
Deal found 3/25$307
This Mytrip deal was found by Cheapflights users on 3/25. 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.
Fri 5/94:35 pmORD - STT
2 stops20h 24mMultiple Airlines
Wed 5/1410:52 amSTT - ORD
3 stops37h 37mMultiple Airlines
Deal found 3/25$309
This Delta deal was found by Cheapflights users on 3/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/281:30 pmORD - SJU
1 stop9h 12mDelta
Wed 6/46:15 amSJU - ORD
1 stop11h 32mDelta
Deal found 3/26$311
This American Airlines deal was found by Cheapflights users on 3/25. 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.
Thu 5/83:15 pmORD - PUJ
1 stop19h 43mAmerican Airlines
Tue 5/131:25 pmPUJ - ORD
1 stop8h 08mAmerican Airlines
Deal found 3/25$322
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 5/66:10 amORD - PUJ
Nonstop4h 41mMultiple Airlines
Wed 5/143:22 pmPUJ - ORD
1 stop10h 02mMultiple Airlines
Deal found 3/25$324
This JetBlue deal was found by Cheapflights users on 3/25. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1110:42 amORD - SJU
1 stop10h 05mJetBlue
Sun 4/2012:16 pmSJU - ORD
1 stop8h 11mJetBlue
Deal found 3/25$325
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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.
Tue 4/155:36 amORD - PUJ
1 stop8h 06mSpirit Airlines
Tue 4/223:48 pmPUJ - ORD
1 stop18h 36mSpirit Airlines
Deal found 3/25$328
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 5/67:00 pmORD - SDQ
1 stop20h 29mMultiple Airlines
Tue 5/133:35 pmSDQ - ORD
1 stop27h 06mMultiple Airlines
Deal found 3/25$333

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 March 26, 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

Tue 4/22

7:00 pm-8:26 am

1 stop12h 26m

San Juan Luis Munoz Marin Intl

Mon 4/28

12:54 am-8:35 am

1 stop8h 41m

$197

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sun 4/27

7:33 pm-10:00 am

1 stop13h 27m

Saint Thomas Island Cyril E King

Sat 5/10

2:41 pm-11:29 pm

1 stop9h 48m

$260

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 5/18

10:33 am-10:53 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Sat 5/24

4:31 pm-12:17 am

1 stop8h 46m

$276

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 4/7

9:50 am-6:28 pm

1 stop7h 38m

San Juan Luis Munoz Marin Intl

Tue 4/8

2:55 am-10:40 am

1 stop8h 45m

$296

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 6/1

6:03 pm-11:54 pm

Nonstop4h 51m

San Juan Luis Munoz Marin Intl

Tue 6/3

1:05 am-8:39 am

1 stop8h 34m

$307

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 5/9

4:35 pm-1:59 pm

2 stops20h 24m

Saint Thomas Island Cyril E King

Wed 5/14

10:52 am-11:29 pm

3 stops37h 37m

$309

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Thu 5/8

3:15 pm-11:58 am

1 stop19h 43m

Punta Cana

Tue 5/13

1:25 pm-8:33 pm

1 stop8h 08m

$322

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 7/17

11:35 am-10:50 pm

1 stop10h 15m

San Juan Luis Munoz Marin Intl

Sun 7/20

1:20 pm-11:25 pm

1 stop11h 05m

$324

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 5/6

6:10 am-11:51 am

Nonstop4h 41m

Punta Cana

Wed 5/14

3:22 pm-12:24 am

1 stop10h 02m

$324

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 4/15

5:36 am-2:42 pm

1 stop8h 06m

Punta Cana

Tue 4/22

3:48 pm-9:24 am

1 stop18h 36m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

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 December is currently the most expensive (average of $336). 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 March 26, 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 March 26, 2025.

The most flights from ORD to 0CB are scheduled on a Monday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 March 26, 2025.
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,891 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Alaska Airlines
8.0
Very good
9,789 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Copa Airlines
7.6
Good
1,393 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,608 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 Spirit Airlines. According to our data, you can fly for as low as $76. Users have also found prices from $148 and $156 on Frontier and Delta, 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: Spirit Airlines (91%), Air Canada (91%), Air New Zealand (91%).

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

    On average you can expect to pay $841 for a flight from Chicago O'Hare Intl Airport to Caribbean. The cheapest flight overall is $69 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $207.

  • 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 December is currently the most expensive (average of $336). 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 March 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$336FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$144Average$347FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$193Average$540FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$226Average$641FlexibilityNo cancel feeOn-time69%
DeltaCheapest$235Average$579FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$293Average$510FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$332Average$637FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$335Average$779FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$385Average$488FlexibilityNo cancel feeOn-time63%
AviancaCheapest$397Average$953FlexibilityNo cancel feeOn-time71%
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