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Caribbean Islands

$72+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Jan 29 — Feb 51
Thu 1/29
Thu 2/5
1 adult, Economy
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Cheap 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 December 30, 2025.

This Priceline deal was found by Cheapflights users on 12/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amORD - SJU
1 stop10h 04mMultiple Airlines
Thu 1/86:30 amSJU - ORD
1 stop10h 58mMultiple Airlines
Deal found 12/27$232
This Priceline deal was found by Cheapflights users on 12/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amORD - SJU
1 stop10h 04mMultiple Airlines
Wed 1/79:19 pmSJU - ORD
1 stop20h 09mMultiple Airlines
Deal found 12/27$238
This JetBlue deal was found by Cheapflights users on 12/28. 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 12/316:45 amORD - SJU
1 stop10h 04mJetBlue
Sat 1/108:00 amSJU - ORD
1 stop11h 43mJetBlue
Deal found 12/28$242
This JetBlue deal was found by Cheapflights users on 12/29. 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 12/316:45 amORD - SJU
1 stop7h 41mJetBlue
Thu 1/1511:06 amSJU - ORD
1 stop10h 30mJetBlue
Deal found 12/29$286
This American Airlines deal was found by Cheapflights users on 12/28. 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.
Wed 12/316:40 amORD - SJU
1 stop11h 03mAmerican Airlines
Thu 1/154:28 pmSJU - ORD
Nonstop5h 32mAmerican Airlines
Deal found 12/28$291
This Delta deal was found by Cheapflights users on 12/28. 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 12/3110:46 amORD - SJU
1 stop10h 34mDelta
Thu 1/157:00 amSJU - ORD
1 stop8h 14mDelta
Deal found 12/28$295
This CheapOair deal was found by Cheapflights users on 12/29. 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 12/315:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Thu 1/151:22 pmSJU - ORD
Nonstop5h 15mSpirit Airlines
Deal found 12/29$319
This Kiwi.com deal was found by Cheapflights users on 12/29. 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.
Wed 12/313:32 pmMDW - SJU
1 stop15h 07mFrontier
Sun 1/1110:47 pmSJU - MDW
1 stop17h 19mFrontier
Deal found 12/29$336
This Kiwi.com deal was found by Cheapflights users on 12/29. 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.
Wed 12/313:32 pmMDW - SJU
1 stop15h 07mFrontier
Fri 1/95:45 amSJU - MDW
1 stop10h 21mFrontier
Deal found 12/29$348
This Kiwi.com deal was found by Cheapflights users on 12/28. 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.
Mon 12/297:10 amORD - PUJ
Nonstop4h 37mFrontier
Wed 12/316:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Deal found 12/28$355
This Frontier deal was found by Cheapflights users on 12/29. 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 12/307:10 amORD - PUJ
Nonstop4h 37mFrontier
Wed 12/316:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Deal found 12/29$361
This Expedia deal was found by Cheapflights users on 12/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:45 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Sun 1/113:35 pmPUJ - ORD
1 stop30h 35mMultiple Airlines
Deal found 12/28$365

Find flight deals from Chicago to Caribbean Islands

Keep the following information in mind while searching for Chicago to Caribbean Islands flight deals. Data was last updated December 30, 2025.

Round-trip from

$192
(CheapOair)

One-way from

$72
(Expedia)

Popular in

December

Cheapest in

April

Average price

$562
From Chicago (CHI) to Caribbean Islands
Search Deals
One-way flight from Chicago (CHI) to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
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 December 30, 2025.
Use the filters below to find and compare flights from Chicago to Caribbean Islands that are best for you.

Fly from

Chicago

Fly to

Caribbean Islands

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/25

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Tue 1/27

11:06 am-7:36 pm

1 stop10h 30m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 3/24

10:56 am-11:23 pm

1 stop11h 27m

San Juan Luis Munoz Marin Intl

Sun 4/5

1:00 pm-9:33 pm

1 stop9h 33m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/1

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Wed 2/4

9:25 am-7:36 pm

1 stop12h 11m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 2/2

7:44 am-7:23 pm

1 stop9h 39m

San Juan Luis Munoz Marin Intl

Wed 2/4

11:06 am-7:36 pm

1 stop10h 30m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/27

12:41 pm-12:29 am

1 stop9h 48m

San Juan Luis Munoz Marin Intl

Fri 3/6

3:05 pm-10:56 pm

1 stop9h 51m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Tue 1/27

11:06 am-7:36 pm

1 stop10h 30m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 2/3

9:40 am-7:23 pm

1 stop7h 43m

San Juan Luis Munoz Marin Intl

Sun 2/8

9:25 am-7:31 pm

1 stop12h 06m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/27

12:41 pm-12:29 am

1 stop9h 48m

San Juan Luis Munoz Marin Intl

Wed 3/4

5:10 am-12:04 pm

1 stop8h 54m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/9

12:41 pm-9:31 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Fri 3/13

1:30 am-10:05 am

1 stop9h 35m

$211

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/2

8:55 am-3:40 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Fri 3/6

8:30 am-11:52 am

Nonstop5h 22m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/28

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Caribbean Islands

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 $127). Flying from Chicago to Caribbean Islands in December is currently the most expensive (average of $221). 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 December 30, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 41% on flights from Chicago to Caribbean Islands by exploring options for tickets in the evening.

What is the cheapest day to fly from Chicago to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Caribbean Islands. Price data was last updated on December 27, 2025.

Travelers seeking maximum savings on their Chicago to Caribbean Islands flight should consider departing on Tuesday mornings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 December 30, 2025.

The most flights from CHI to zzEPX are scheduled on a Saturday (13 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (10 on average).

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 30, 2025.
Read through reviews of airlines operating flights from Chicago to Caribbean Islands, such as Delta, United Airlines, and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,017 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.1

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,017 reviews
Delta
7.9
Good
8,017 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.1

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,121 reviews
Delta
7.9
Good
8,017 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.1

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,073 reviews
Delta
7.9
Good
8,017 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.1

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,235 reviews
Delta
7.9
Good
8,017 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.1

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.7
Fair
3,065 reviews
Delta
7.9
Good
8,017 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.1

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • How long is the flight from Chicago to Caribbean Islands?

    For as low as $196, JetBlue can have you in Caribbean Islands from Chicago in 8h 20m. Chicago and Caribbean Islands are separated by a distance of 2073 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago to Caribbean Islands one-way?

    $65 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on JetBlue and Spirit Airlines, with prices starting from $84 and $92, 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 Midway - San Juan Luis Munoz Marin 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 Air Canada (80%), United Airlines (80%) or Air New Zealand (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 $714, our data indicates the cheapest price to be $104. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $144.

  • 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 $127). Flying from Chicago to Caribbean Islands in December is currently the most expensive (average of $221). 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 2,558,603 searches. Data last updated December 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$115Average$450FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$136Average$449FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$375FlexibilityNo cancel feeOn-time65%
DeltaCheapest$186Average$577FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
ArajetCheapest$199Average$335FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$612FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$277Average$639FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$337Average$615FlexibilityNo cancel feeOn-time71%

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