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$88+ 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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Dec 7 — Dec 141
Sat 12/7
Sat 12/14
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 2, 2024.

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 December 2, 2024.

This Frontier deal was found by Cheapflights users on 12/1. 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.
Tue 12/171:54 pmORD - SJU
1 stop8h 47mFrontier
Wed 12/253:54 amSJU - ORD
1 stop8h 10mFrontier
Deal found 12/1$168
This Cheapflightsfares deal was found by Cheapflights users on 12/1. 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.
Mon 12/161:13 pmORD - SJU
1 stop10h 27mSpirit Airlines
Sat 12/218:31 pmSJU - ORD
Nonstop5h 27mSpirit Airlines
Deal found 12/1$185
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/171:54 pmORD - SJU
1 stop8h 47mMultiple Airlines
Sun 12/228:31 pmSJU - ORD
Nonstop5h 27mMultiple Airlines
Deal found 12/1$186
This United Airlines deal was found by Cheapflights users on 12/1. 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.
Mon 12/92:50 pmORD - SJU
1 stop7h 46mUnited Airlines
Fri 12/132:05 amSJU - ORD
1 stop9h 38mUnited Airlines
Deal found 12/1$210
This American Airlines deal was found by Cheapflights users on 12/1. 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.
Sun 12/88:05 amORD - SJU
1 stop10h 50mAmerican Airlines
Fri 12/134:45 pmSJU - ORD
1 stop9h 29mAmerican Airlines
Deal found 12/1$270
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Fri 12/136:07 pmORD - PUJ
1 stop15h 24mMultiple Airlines
Wed 12/182:35 pmPUJ - ORD
1 stop11h 23mMultiple Airlines
Deal found 12/2$276
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Fri 12/136:07 pmORD - PUJ
1 stop15h 24mFrontier
Fri 12/206:02 pmPUJ - ORD
2 stops31h 55mFrontier
Deal found 12/1$302
This Delta deal was found by Cheapflights users on 12/1. 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 12/117:00 amORD - SJU
1 stop8h 15mDelta
Tue 12/171:49 pmSJU - ORD
1 stop8h 03mDelta
Deal found 12/1$324
This CheapOair deal was found by Cheapflights users on 12/2. 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.
Wed 12/188:14 pmORD - STT
1 stop15h 34mSpirit Airlines
Wed 12/2511:44 amSTT - ORD
2 stops22h 03mSpirit Airlines
Deal found 12/2$325
This CheapOair deal was found by Cheapflights users on 12/1. 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 12/315:00 amORD - PUJ
1 stop8h 55mSpirit Airlines
Sun 1/124:50 pmPUJ - ORD
1 stop19h 17mSpirit Airlines
Deal found 12/1$342
This American Airlines deal was found by Cheapflights users on 11/30. 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 12/196:35 pmORD - PUJ
1 stop15h 21mAmerican Airlines
Tue 12/243:47 pmPUJ - ORD
Nonstop5h 15mAmerican Airlines
Deal found 11/30$378
This Delta deal was found by Cheapflights users on 12/2. 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.
Sun 12/85:40 amORD - PUJ
1 stop8h 44mDelta
Fri 12/135:49 pmPUJ - ORD
1 stop8h 09mDelta
Deal found 12/2$393

Find flights from O'Hare Intl to Caribbean within your budget

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 2,650,959 searches. Data last updated December 2, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/22

1:44 pm-8:19 pm

Nonstop4h 35m

San Juan Luis Munoz Marin Intl

Mon 2/24

4:00 am-10:38 pm

1 stop20h 38m

$168

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 12/15

9:35 am-10:38 am

1 stop23h 03m

San Juan Luis Munoz Marin Intl

Sun 12/22

6:00 am-9:54 am

1 stop29h 54m

$170

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 1/31

1:44 pm-8:21 pm

Nonstop4h 37m

San Juan Luis Munoz Marin Intl

Sat 2/22

9:26 pm-12:55 am

Nonstop5h 29m

$173

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 1/21

1:15 pm-10:22 pm

1 stop7h 07m

San Juan Luis Munoz Marin Intl

Fri 1/24

2:05 am-9:35 am

1 stop9h 30m

$210

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 2/14

6:01 pm-10:40 am

1 stop14h 39m

Punta Cana

Fri 2/21

3:15 pm-7:18 am

1 stop18h 03m

$258

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 1/11

5:10 am-3:49 pm

1 stop8h 39m

Punta Cana

Sat 1/18

4:54 pm-11:32 pm

1 stop8h 38m

$268

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 12/13

6:07 pm-11:31 am

1 stop15h 24m

Punta Cana

Wed 12/18

2:35 pm-11:58 pm

1 stop11h 23m

$276

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/24

10:02 pm-5:19 pm

2 stops17h 17m

Simpson Bay Princess Juliana

Sat 2/1

6:29 pm-12:51 am

1 stop8h 22m

$310

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 12/12

9:45 am-11:50 pm

1 stop12h 05m

San Juan Luis Munoz Marin Intl

Fri 12/13

3:36 pm-7:06 pm

Nonstop5h 30m

$314

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 2/1

3:56 pm-10:46 am

1 stop16h 50m

Saint Thomas Island Cyril E King

Sat 2/8

11:51 am-8:13 pm

1 stop10h 22m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

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.

Travel insights for flights from O'Hare Intl to Caribbean

Get recent, data-driven insights about flights from O'Hare Intl to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $334). 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 December 2, 2024.

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 December 2, 2024.

The most flights from ORD to 0CB are scheduled on a Monday (8 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (6 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 December 2, 2024.
Southwest
8.1
Very good
4,951 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Southwest
8.1
Very good
4,951 reviews
Southwest
8.1
Very good
4,951 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Delta
8.0
Very good
8,698 reviews
Southwest
8.1
Very good
4,951 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Alaska Airlines
8.0
Very good
9,513 reviews
Southwest
8.1
Very good
4,951 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

KLM
7.8
Good
1,343 reviews
Southwest
8.1
Very good
4,951 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Copa Airlines
7.7
Good
1,765 reviews
Southwest
8.1
Very good
4,951 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

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 $88. Users have also found prices from $90 and $105 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 - 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 (89%), United Airlines (89%), Air New Zealand (89%).

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

    On average you can expect to pay $657 for a flight from Chicago O'Hare Intl Airport to Caribbean. The cheapest flight overall is $79 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 $254). Flying from Chicago O'Hare Intl Airport to Caribbean in March is currently the most expensive (average of $334). 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 2,650,959 searches. Data last updated December 2, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$340FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$137Average$513FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$166Average$365FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$262Average$619FlexibilityNo cancel feeOn-time69%
DeltaCheapest$324Average$547FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$324Average$620FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$379Average$489FlexibilityNo cancel feeOn-time63%
Copa AirlinesCheapest$379Average$518FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$514Average$792FlexibilityNo cancel feeOn-time67%
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