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Caribbean Islands

$57+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Nov 19 — Nov 261
1 adult
Tue 11/19
Tue 11/26
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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 November 14, 2024.

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 November 14, 2024.

This FlightHub deal was found by Cheapflights users on 11/14. 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.
Sun 12/89:58 amORD - SJU
1 stop8h 24mSpirit Airlines
Fri 12/132:17 pmSJU - ORD
Nonstop5h 30mSpirit Airlines
Deal found 11/14$174
This Trip.com deal was found by Cheapflights users on 11/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/157:25 amMDW - SJU
1 stop16h 32mFrontier
Thu 12/193:59 amSJU - MDW
1 stop7h 32mFrontier
Deal found 11/13$174
This FlightHub deal was found by Cheapflights users on 11/14. 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.
Thu 11/282:46 pmORD - SJU
1 stop28h 45mFrontier
Wed 12/49:15 pmSJU - ORD
1 stop13h 09mFrontier
Deal found 11/14$175
This FlightHub deal was found by Cheapflights users on 11/14. 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.
Sun 12/89:32 pmORD - SJU
1 stop12h 29mMultiple Airlines
Thu 12/129:49 pmSJU - ORD
1 stop14h 05mMultiple Airlines
Deal found 11/14$178
This eDestinos deal was found by Cheapflights users on 11/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/97:25 amMDW - SJU
1 stop16h 32mMultiple Airlines
Fri 12/136:40 pmSJU - MDW
2 stops30h 49mMultiple Airlines
Deal found 11/12$201
This FlightHub deal was found by Cheapflights users on 11/14. 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.
Fri 12/136:07 pmORD - PUJ
1 stop15h 24mFrontier
Fri 12/205:00 pmPUJ - ORD
Nonstop5h 31mFrontier
Deal found 11/14$275
This Kiwi.com deal was found by Cheapflights users on 11/14. 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.
Sat 12/75:00 amORD - PUJ
1 stop8h 48mMultiple Airlines
Thu 12/126:45 pmPUJ - ORD
Nonstop5h 14mMultiple Airlines
Deal found 11/14$281
This United Airlines deal was found by Cheapflights users on 11/14. 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 12/92:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
Mon 12/162:05 amSJU - ORD
1 stop8h 54mUnited Airlines
Deal found 11/14$286
This FareScan deal was found by Cheapflights users on 11/14. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/36:00 amORD - STT
3 stops26h 51mSpirit Airlines
Tue 12/1011:56 amSTT - ORD
2 stops14h 38mSpirit Airlines
Deal found 11/14$310
This FlightHub deal was found by Cheapflights users on 11/14. 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.
Fri 12/136:48 pmMDW - PUJ
1 stop14h 43mFrontier
Fri 12/201:59 pmPUJ - MDW
1 stop11h 15mFrontier
Deal found 11/14$318
This JetBlue deal was found by Cheapflights users on 11/13. 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.
Wed 12/1110:14 amORD - SJU
1 stop8h 06mJetBlue
Tue 12/177:00 amSJU - ORD
1 stop10h 53mJetBlue
Deal found 11/13$321
This Southwest deal was found by Cheapflights users on 11/13. 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.
Sun 12/811:40 amMDW - SJU
2 stops11h 00mSouthwest
Thu 12/126:10 amSJU - MDW
1 stop10h 05mSouthwest
Deal found 11/13$325

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 2,752,363 searches. Data last updated November 14, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 12/8

9:58 am-8:22 pm

1 stop8h 24m

San Juan Luis Munoz Marin Intl

Fri 12/13

2:17 pm-5:47 pm

Nonstop5h 30m

$174

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 12/8

7:25 am-1:57 am

1 stop16h 32m

San Juan Luis Munoz Marin Intl

Thu 12/12

6:20 am-5:18 pm

1 stop12h 58m

$174

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 11/28

8:51 am-4:45 am

1 stop17h 54m

San Juan Luis Munoz Marin Intl

Thu 12/5

7:16 pm-9:54 am

1 stop16h 38m

$175

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/15

8:00 am-11:25 pm

1 stop13h 25m

San Juan Luis Munoz Marin Intl

Sat 2/22

9:59 pm-12:58 am

Nonstop4h 59m

$177

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/15

1:20 pm-12:40 am

1 stop9h 20m

San Juan Luis Munoz Marin Intl

Thu 1/23

2:55 pm-7:45 pm

1 stop6h 50m

$200

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 12/6

6:48 pm-8:45 pm

2 stops47h 57m

San Juan Luis Munoz Marin Intl

Wed 12/11

6:40 pm-3:12 pm

1 stop22h 32m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 12/11

9:00 am-3:38 pm

Nonstop4h 38m

San Juan Luis Munoz Marin Intl

Wed 12/18

8:35 am-11:54 am

Nonstop5h 19m

$240

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 1/11

6:10 am-12:39 pm

Nonstop4h 29m

Punta Cana

Thu 1/16

4:54 pm-11:02 pm

1 stop8h 08m

$274

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 12/13

6:07 pm-11:31 am

1 stop15h 24m

Punta Cana

Fri 12/20

5:00 pm-8:31 pm

Nonstop5h 31m

$275

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 12/13

6:48 pm-11:31 am

1 stop14h 43m

Punta Cana

Mon 12/16

12:46 pm-1:09 pm

1 stop26h 23m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

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 $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 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 November 14, 2024.

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 November 14, 2024.

The most flights from CHI to zzEPX are scheduled on a Thursday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 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 November 14, 2024.
Peruse reviews from past customers who have flown with Frontier, Spirit Airlines and Southwest 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
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

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

Southwest
8.1
Very good
5,045 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

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

Delta
8.0
Very good
8,788 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

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

Alaska Airlines
8.0
Very good
9,439 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

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

KLM
7.8
Good
1,346 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

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

Copa Airlines
7.8
Good
1,809 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

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 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?

    $57 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and Southwest, with prices starting from $58 and $100, 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 Spirit Airlines (88%), Air Canada (87%) or United Airlines (87%) 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 $622, our data indicates the cheapest price to be $88. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $118.

  • 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 $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.

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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 9 airlines flying from Chicago to Caribbean Islands

Discover the top 9 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 2,752,363 searches. Data last updated November 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$352FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$137Average$532FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$166Average$353FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$267Average$628FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$275Average$686FlexibilityNo cancel feeOn-time63%
DeltaCheapest$275Average$613FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$324Average$617FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$379Average$518FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$514Average$907FlexibilityNo cancel feeOn-time67%
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