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Caribbean Islands

$82+ Cheap flights from Chicago (CHI) 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
1 adult, Economy
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Cheap flight deals from Chicago to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 enero 21, 2025.

Round-trip from

$160
(Booking.com)

One-way from

$82
(Cheapflightsfares)
From Chicago (CHI) to Caribbean Islands
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One-way flight from Chicago (CHI) to Caribbean Islands
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Find flight deals from Chicago to Caribbean Islands

Cheapest flights from Chicago to Caribbean Islands
Explore the most affordable flight options available from Chicago to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/2512:21 pmORD - SJU
Nonstop4h 31mSpirit Airlines
jue. 3/67:00 amSJU - ORD
Nonstop5h 36mSpirit Airlines
Deal found 1/21$160
This FlightHub deal was found by Cheapflights users on 1/21. 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.
mar. 4/12:36 pmMDW - SJU
1 stop8h 18mFrontier
lun. 4/75:01 amSJU - MDW
1 stop15h 45mFrontier
Deal found 1/21$160
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
mar. 3/43:14 pmORD - SJU
1 stop16h 35mMultiple Airlines
mié. 3/125:45 pmSJU - ORD
1 stop7h 22mMultiple Airlines
Deal found 1/20$161
This Frontier deal was found by Cheapflights users on 1/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/217:18 pmORD - SJU
1 stop12h 31mFrontier
mar. 2/259:30 pmSJU - ORD
1 stop13h 57mFrontier
Deal found 1/21$170
This Southwest deal was found by Cheapflights users on 1/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 2/21:20 pmMDW - SJU
2 stops9h 30mSouthwest
vie. 2/71:45 pmSJU - MDW
1 stop10h 15mSouthwest
Deal found 1/20$235
This United Airlines deal was found by Cheapflights users on 1/21. 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.
dom. 2/210:35 amORD - SJU
1 stop8h 53mUnited Airlines
mié. 2/52:05 amSJU - ORD
1 stop9h 35mUnited Airlines
Deal found 1/21$245
This Kiwi.com deal was found by Cheapflights users on 1/20. 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. 2/78:12 pmORD - PUJ
1 stop12h 58mMultiple Airlines
jue. 2/202:29 pmPUJ - ORD
1 stop10h 51mMultiple Airlines
Deal found 1/20$295
This JetBlue deal was found by Cheapflights users on 1/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/1912:45 pmORD - SJU
1 stop10h 28mJetBlue
jue. 2/275:10 amSJU - ORD
1 stop7h 49mJetBlue
Deal found 1/20$303
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/16:10 amORD - PUJ
Nonstop4h 50mFrontier
vie. 2/76:10 pmPUJ - ORD
Nonstop5h 17mFrontier
Deal found 1/21$304
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/247:10 amORD - PUJ
1 stop6h 33mSpirit Airlines
vie. 2/284:48 pmPUJ - ORD
1 stop9h 10mSpirit Airlines
Deal found 1/21$306
This CheapOair deal was found by Cheapflights users on 1/21. 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.
mar. 4/12:36 pmMDW - PUJ
1 stop18h 42mFrontier
lun. 4/72:49 pmPUJ - MDW
1 stop10h 01mFrontier
Deal found 1/21$309
This Mytrip deal was found by Cheapflights users on 1/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/265:15 amORD - STT
3 stops27h 31mSpirit Airlines
lun. 3/311:41 amSTT - ORD
3 stops25h 35mSpirit Airlines
Deal found 1/21$312

Find flights from Chicago to Caribbean Islands within your budget

Customize your flight search to find flights from Chicago 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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 2/25

12:21 pm-6:52 pm

Nonstop4h 31m

San Juan Luis Munoz Marin Intl

jue. 3/6

7:00 am-10:36 am

Nonstop5h 36m

$160

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

mar. 4/1

2:36 pm-11:54 pm

1 stop8h 18m

San Juan Luis Munoz Marin Intl

lun. 4/7

5:01 am-7:46 pm

1 stop15h 45m

$160

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 3/4

3:14 pm-9:49 am

1 stop16h 35m

San Juan Luis Munoz Marin Intl

mié. 3/12

5:45 pm-12:07 am

1 stop7h 22m

$161

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

vie. 2/21

7:18 pm-9:49 am

1 stop12h 31m

San Juan Luis Munoz Marin Intl

mar. 2/25

9:30 pm-9:27 am

1 stop13h 57m

$170

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

dom. 2/2

1:20 pm-12:50 am

2 stops9h 30m

San Juan Luis Munoz Marin Intl

vie. 2/7

1:45 pm-10:00 pm

1 stop10h 15m

$235

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

dom. 2/2

10:35 am-9:28 pm

1 stop8h 53m

San Juan Luis Munoz Marin Intl

lun. 12/8

2:05 am-9:37 am

1 stop9h 32m

$245

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

vie. 2/7

8:12 pm-11:10 am

1 stop12h 58m

Punta Cana

jue. 2/20

2:29 pm-11:20 pm

1 stop10h 51m

$295

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 2/19

12:45 pm-1:13 am

1 stop10h 28m

San Juan Luis Munoz Marin Intl

jue. 2/27

5:10 am-10:59 am

1 stop7h 49m

$303

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

lun. 2/24

7:10 am-3:43 pm

1 stop6h 33m

Punta Cana

vie. 2/28

4:48 pm-11:58 pm

1 stop9h 10m

$306

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

mar. 4/1

2:36 pm-10:18 am

1 stop18h 42m

Punta Cana

lun. 4/7

2:49 pm-11:50 pm

1 stop10h 01m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Caribbean Islands

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

Get recent, data-driven insights about flights from Chicago to Caribbean Islands including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Chicago to Caribbean Islands (average of $254). Flying from Chicago to Caribbean Islands in March is currently the most expensive (average of $378). 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 CHI to EPX?

Find hourly flight availability from Chicago 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 enero 21, 2025.

When flying from Chicago 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 to Caribbean Islands

Explore weekly flight availability from Chicago 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 enero 21, 2025.

The most flights from CHI to zzEPX are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 enero 21, 2025.
Peruse reviews from past customers who have flown with Frontier, Delta and Spirit Airlines from Chicago to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

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.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

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.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

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.

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

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.

KLM
7.8
Good
1,341 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

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.

Copa Airlines
7.7
Good
1,662 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

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 Chicago 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 to Caribbean Islands one-way?

    $82 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and Southwest, with prices starting from $83 and $118, respectively.

  • What are the most popular routes from Chicago to Caribbean Islands?

    When deciding which route to take from Chicago to Caribbean Islands consider 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 as they are the most popular.

  • What are the most reliable airlines from Chicago to Caribbean Islands?

    No one likes to see their flight delayed. When booking a flight from Chicago to Caribbean Islands consider choosing American Airlines (83%), Alaska Airlines (83%) or Spirit Airlines (80%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Caribbean Islands?

    Looking for the cheapest flight from Chicago to Caribbean Islands? While on average our users pay $1,243, our data indicates the cheapest price to be $109. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $130.

  • Can I find deals for flights from Chicago to Caribbean Islands that include hotel bookings?

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

  • How can I find direct flights from Chicago to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Caribbean Islands.

  • Can I find deals for business class flights from Chicago to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Chicago 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 to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Caribbean Islands (average of $254). Flying from Chicago to Caribbean Islands in March is currently the most expensive (average of $378). 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 Chicago to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 10 airlines flying from Chicago to Caribbean Islands

Discover the top 10 airlines that operate flights from Chicago 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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$366FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$156Average$355FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$173Average$507FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$226Average$518FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$256Average$640FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$317Average$641FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$322Average$625FlexibilityNo cancel feeOn-time71%
DeltaCheapest$324Average$678FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$335Average$761FlexibilityNo cancel feeOn-time67%
AviancaCheapest$1,422Average$1,422FlexibilityNo cancel feeOn-time71%
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