Caribbean Islands

$92+ Cheap flights from O'Hare Intl (ORD) to Caribbean Islands

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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Dec 23 — Dec 301
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Cheap flight deals from O'Hare Intl to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Caribbean Islands (zzEPX). 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 18, 2024.

Round-trip from

$161
(Kiwi.com)

One-way from

$92
(Kiwi.com)
From Chicago O'Hare Intl to Caribbean Islands
One-way flight from Chicago O'Hare Intl to Caribbean Islands

Find flight deals from O'Hare Intl to Caribbean Islands

Cheapest flights from O'Hare Intl to Caribbean Islands
Explore the most affordable flight options available from O'Hare Intl to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2024.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/311:47 pmORD - SJU
1 stop8h 54mMultiple Airlines
Tue 1/149:26 pmSJU - ORD
Nonstop5h 25mMultiple Airlines
Deal found 12/17$191
This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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 12/311:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Tue 1/149:26 pmSJU - ORD
Nonstop5h 25mSpirit Airlines
Deal found 12/17$209
This Frontier deal was found by Cheapflights users on 12/18. 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 12/304:41 pmORD - SJU
1 stop11h 49mFrontier
Sat 1/189:15 pmSJU - ORD
1 stop14h 37mFrontier
Deal found 12/18$278
This Kiwi.com deal was found by Cheapflights users on 12/18. 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 12/316:10 amORD - PUJ
Nonstop4h 29mFrontier
Tue 12/316:45 pmPUJ - ORD
Nonstop5h 14mFrontier
Deal found 12/18$315
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/315:11 pmORD - STT
1 stop15h 28mSpirit Airlines
Thu 1/911:51 amSTT - ORD
1 stop10h 22mSpirit Airlines
Deal found 12/16$379
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/316:39 pmORD - PUJ
1 stop17h 31mAmerican Airlines
Thu 1/95:40 pmPUJ - ORD
1 stop17h 05mAmerican Airlines
Deal found 12/17$383
This CheapOair deal was found by Cheapflights users on 12/17. 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 12/316:10 amORD - PUJ
Nonstop4h 29mMultiple Airlines
Sun 1/124:50 pmPUJ - ORD
1 stop8h 42mMultiple Airlines
Deal found 12/17$408
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/316:39 pmORD - SJU
1 stop16h 55mAmerican Airlines
Sun 7/273:15 pmSJU - ORD
Nonstop5h 10mAmerican Airlines
Deal found 12/17$420
This CheapOair deal was found by Cheapflights users on 12/17. 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 12/313:31 pmORD - MBJ
1 stop21h 14mSpirit Airlines
Wed 1/221:16 pmMBJ - ORD
1 stop7h 57mSpirit Airlines
Deal found 12/17$451
This Delta deal was found by Cheapflights users on 12/17. 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.
Thu 12/195:40 amORD - PUJ
1 stop8h 54mDelta
Thu 12/262:40 pmPUJ - ORD
1 stop10h 12mDelta
Deal found 12/17$478
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/315:07 pmORD - NAS
1 stop16h 53mMultiple Airlines
Thu 1/94:00 pmNAS - ORD
1 stop8h 32mMultiple Airlines
Deal found 12/17$485
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/319:05 amORD - MBJ
Nonstop4h 15mAmerican Airlines
Wed 1/224:00 pmMBJ - ORD
1 stop8h 59mAmerican Airlines
Deal found 12/17$500

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

Customize your flight search to find flights from O'Hare Intl to Caribbean Islands 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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/8

3:31 pm-1:25 am

1 stop7h 54m

San Juan Luis Munoz Marin Intl

Fri 1/17

9:26 pm-12:51 am

Nonstop5h 25m

$161

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 1/23

6:50 am-12:36 am

1 stop15h 46m

San Juan Luis Munoz Marin Intl

Sun 1/26

6:55 pm-4:23 pm

1 stop23h 28m

$162

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/27

1:44 pm-8:21 pm

Nonstop4h 37m

San Juan Luis Munoz Marin Intl

Mon 2/3

6:00 am-10:16 pm

1 stop18h 16m

$163

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/12

11:15 am-10:22 pm

1 stop9h 07m

San Juan Luis Munoz Marin Intl

Wed 1/22

2:05 am-9:40 am

1 stop9h 35m

$234

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 1/25

5:11 am-3:45 pm

1 stop8h 34m

Punta Cana

Fri 1/31

6:10 pm-9:27 pm

Nonstop5h 17m

$249

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 1/29

6:10 am-1:00 pm

Nonstop4h 50m

Punta Cana

Fri 1/31

6:10 pm-9:27 pm

Nonstop5h 17m

$255

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/27

12:25 pm-9:38 pm

1 stop7h 13m

San Juan Luis Munoz Marin Intl

Sat 2/1

6:00 am-12:14 pm

1 stop8h 14m

$264

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 2/1

5:11 am-3:45 pm

1 stop8h 34m

Punta Cana

Sat 2/8

4:50 pm-11:32 pm

1 stop8h 42m

$281

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 2/25

11:25 am-12:40 am

2 stops11h 15m

San Juan Luis Munoz Marin Intl

Tue 3/4

12:15 pm-10:20 pm

2 stops12h 05m

$309

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sun 1/12

10:29 am-10:46 am

2 stops22h 17m

Saint Thomas Island Cyril E King

Sat 1/18

11:51 am-11:32 am

2 stops25h 41m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

Get recent, data-driven insights about flights from O'Hare Intl to Caribbean Islands 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 Islands?

Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean Islands (average of $254). Flying from Chicago O'Hare Intl Airport to Caribbean Islands 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 EPX?

Find hourly flight availability from O'Hare Intl to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2024.

When flying from Chicago O'Hare Intl Airport to Caribbean Islands, 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 Islands

Explore weekly flight availability from O'Hare Intl to Caribbean Islands. 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 18, 2024.

The most flights from ORD to zzEPX are scheduled on a Monday (10 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (8 on average).

Rainfall in Caribbean Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated December 18, 2024.
Read reviews from past customers who have flown United Airlines, Spirit Airlines and American Airlines from Chicago to Caribbean Islands. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
4,848 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,848 reviews
8.1
Very good
4,848 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,604 reviews
8.1
Very good
4,848 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
9,554 reviews
8.1
Very good
4,848 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.7
Good
1,721 reviews
8.1
Very good
4,848 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
9,055 reviews
8.1
Very good
4,848 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Caribbean Islands. 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 Islands one-way?

    The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Caribbean Islands are Frontier ($92), Spirit Airlines ($93), and United Airlines ($113).

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

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

    The top 3 most reliable airlines when flying from Chicago O'Hare Intl Airport to Caribbean Islands are American Airlines (100%), Alaska Airlines (100%) and Air Canada (85%).

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

    Looking at all options, your cheapest flight can be booked for $64. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $126 on average our data indicates $687 when flying from Chicago O'Hare Intl Airport to Caribbean Islands.

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

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

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

    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 Islands.

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

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

    Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean Islands (average of $254). Flying from Chicago O'Hare Intl Airport to Caribbean Islands 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 Islands

See prices for flight routes from nearby airports that may be better suited for you.

Top 9 airlines flying from O'Hare Intl to Caribbean Islands

Discover the top 9 airlines that operate flights from O'Hare Intl to Caribbean Islands. 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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$342FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$137Average$489FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$159Average$366FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$254Average$623FlexibilityNo cancel feeOn-time69%
DeltaCheapest$307Average$528FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$324Average$618FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$379Average$489FlexibilityNo cancel feeOn-time63%
Copa AirlinesCheapest$379Average$496FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$514Average$753FlexibilityNo cancel feeOn-time67%
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