Caribbean Islands

$88+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
nov. 26 — dic. 31
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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 noviembre 21, 2024.

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 noviembre 21, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
sáb. 12/71:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
jue. 12/122:17 pmSJU - ORD
Nonstop5h 30mSpirit Airlines
Deal found 11/20$170
This FlightHub deal was found by Cheapflights users on 11/21. 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.
dom. 12/89:35 amORD - SJU
1 stop26h 19mFrontier
jue. 12/125:05 pmSJU - ORD
1 stop18h 49mFrontier
Deal found 11/21$175
This Justfly.com deal was found by Cheapflights users on 11/20. 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.
dom. 12/89:35 amORD - SJU
1 stop26h 19mMultiple Airlines
jue. 12/122:17 pmSJU - ORD
Nonstop5h 30mMultiple Airlines
Deal found 11/20$177
This United Airlines deal was found by Cheapflights users on 11/21. 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.
lun. 12/92:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
vie. 12/132:05 amSJU - ORD
1 stop10h 48mUnited Airlines
Deal found 11/21$226
This FlightHub deal was found by Cheapflights users on 11/21. 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. 12/46:00 amORD - PUJ
Nonstop4h 29mFrontier
mié. 12/115:00 pmPUJ - ORD
Nonstop5h 31mFrontier
Deal found 11/21$269
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
vie. 12/136:07 pmORD - PUJ
1 stop15h 24mMultiple Airlines
mié. 12/182:35 pmPUJ - ORD
1 stop7h 38mMultiple Airlines
Deal found 11/20$281
This FlightHub deal was found by Cheapflights users on 11/20. 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.
vie. 12/137:45 pmORD - STT
1 stop15h 38mSpirit Airlines
vie. 1/1711:46 amSTT - ORD
1 stop13h 16mSpirit Airlines
Deal found 11/20$324
This Mytrip deal was found by Cheapflights users on 11/20. 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.
lun. 12/239:25 pmORD - STT
3 stops35h 14mMultiple Airlines
mar. 12/3111:44 amSTT - ORD
1 stop10h 07mMultiple Airlines
Deal found 11/20$337
This CheapOair deal was found by Cheapflights users on 11/21. 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.
dom. 12/85:00 amORD - PUJ
1 stop8h 48mSpirit Airlines
vie. 12/134:43 pmPUJ - ORD
1 stop25h 23mSpirit Airlines
Deal found 11/21$351
This American Airlines deal was found by Cheapflights users on 11/21. 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.
lun. 12/305:35 pmORD - PUJ
1 stop16h 39mAmerican Airlines
vie. 1/105:05 pmPUJ - ORD
1 stop17h 25mAmerican Airlines
Deal found 11/21$353
This United Airlines deal was found by Cheapflights users on 11/20. 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.
mar. 12/108:48 amORD - PUJ
1 stop6h 47mUnited Airlines
jue. 12/193:15 pmPUJ - ORD
1 stop10h 05mUnited Airlines
Deal found 11/20$373
This Delta deal was found by Cheapflights users on 11/19. 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.
lun. 12/26:00 amORD - PUJ
1 stop8h 40mDelta
sáb. 12/75:49 pmPUJ - ORD
1 stop8h 09mDelta
Deal found 11/19$423

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 2,612,795 searches. Data last updated noviembre 21, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 12/7

1:00 pm-7:36 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

jue. 12/12

2:17 pm-5:47 pm

Nonstop5h 30m

$170

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

dom. 2/2

4:18 pm-10:37 am

1 stop16h 19m

San Juan Luis Munoz Marin Intl

jue. 2/6

9:49 pm-9:52 am

1 stop14h 03m

$173

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 1/8

8:14 pm-11:18 am

1 stop13h 04m

San Juan Luis Munoz Marin Intl

mié. 1/15

4:49 pm-1:50 pm

1 stop23h 01m

$174

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 12/9

2:20 pm-8:55 pm

Nonstop4h 35m

San Juan Luis Munoz Marin Intl

vie. 12/13

2:05 am-9:43 am

1 stop9h 38m

$226

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mié. 12/4

6:00 am-12:29 pm

Nonstop4h 29m

Punta Cana

mié. 12/11

5:00 pm-8:31 pm

Nonstop5h 31m

$265

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

sáb. 1/25

5:10 am-3:49 pm

1 stop8h 39m

Punta Cana

mar. 1/28

6:54 pm-10:11 pm

Nonstop5h 17m

$268

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

lun. 1/13

5:10 am-3:49 pm

1 stop8h 39m

Punta Cana

sáb. 1/18

4:54 pm-11:02 pm

1 stop8h 08m

$297

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

vie. 1/3

5:11 pm-10:39 am

1 stop15h 28m

Saint Thomas Island Cyril E King

vie. 1/10

11:46 am-11:02 pm

1 stop13h 16m

$324

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

lun. 12/23

9:25 pm-10:39 am

3 stops35h 14m

Saint Thomas Island Cyril E King

mar. 12/31

11:44 am-7:51 pm

1 stop10h 07m

$337

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 1/14

8:05 am-2:35 pm

Nonstop4h 30m

Punta Cana

mar. 1/28

5:40 pm-8:45 am

1 stop17h 05m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

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 $335). 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 noviembre 21, 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 noviembre 21, 2024.

The most flights from ORD to zzEPX are scheduled on a Thursday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 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 noviembre 21, 2024.
Read reviews from past customers who have flown Spirit Airlines, Frontier and United 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
5,005 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

8.1
Very good
5,005 reviews
8.1
Very good
5,005 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

8.0
Very good
8,755 reviews
8.1
Very good
5,005 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

8.0
Very good
9,464 reviews
8.1
Very good
5,005 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

7.8
Good
1,779 reviews
8.1
Very good
5,005 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

7.4
Good
9,172 reviews
8.1
Very good
5,005 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 ($88), Spirit Airlines ($91), and United Airlines ($105).

  • 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 Air Canada (90%), United Airlines (90%) and Air New Zealand (90%).

  • 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 $90. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $117 on average our data indicates $741 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 $335). 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 2,612,795 searches. Data last updated noviembre 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$339FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$137Average$521FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$166Average$364FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$267Average$618FlexibilityNo cancel feeOn-time69%
DeltaCheapest$324Average$529FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$324Average$618FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$379Average$489FlexibilityNo cancel feeOn-time63%
Copa AirlinesCheapest$379Average$518FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$514Average$872FlexibilityNo cancel feeOn-time67%
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