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Caribbean Islands

$101+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheap 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 November 6, 2025.

Round-trip from

$212
(Kiwi.com)

One-way from

$101
(Expedia)

Popular in

December

Cheapest in

April

Average price

$381
From Chicago (CHI) to Caribbean Islands
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One-way flight from Chicago (CHI) to Caribbean Islands
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Highest demand for flights based on searches. 7% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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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 November 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Thu 11/2010:12 amORD - SJU
1 stop8h 15mMultiple Airlines
Sun 11/232:25 amSJU - ORD
1 stop10h 46mMultiple Airlines
Deal found 11/3$212
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/28:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Tue 12/96:00 amSJU - ORD
1 stop16h 09mSpirit Airlines
Deal found 11/4$213
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/244:58 pmORD - SJU
1 stop15h 51mSpirit Airlines
Thu 12/48:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 11/4$215
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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.
Thu 11/205:00 amORD - SJU
1 stop13h 27mSpirit Airlines
Thu 12/49:00 amSJU - ORD
Nonstop5h 23mSpirit Airlines
Deal found 11/4$216
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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.
Wed 12/38:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Sat 12/67:31 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 11/4$217
This Trip.com deal was found by Cheapflights users on 11/3. 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.
Tue 11/2511:48 amORD - SJU
1 stop9h 56mMultiple Airlines
Thu 11/274:12 pmSJU - ORD
Nonstop5h 11mMultiple Airlines
Deal found 11/3$218
This Priceline deal was found by Cheapflights users on 11/4. 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.
Sun 12/76:00 amORD - SJU
1 stop12h 08mMultiple Airlines
Mon 12/84:10 amSJU - ORD
2 stops11h 48mMultiple Airlines
Deal found 11/4$219
This Mytrip deal was found by Cheapflights users on 11/3. 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.
Tue 12/28:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Fri 12/124:10 amSJU - ORD
2 stops19h 38mSpirit Airlines
Deal found 11/3$220
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/178:00 amORD - SJU
Nonstop4h 36mSpirit Airlines
Fri 12/54:10 amSJU - ORD
1 stop8h 58mSpirit Airlines
Deal found 11/4$221
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Thu 12/42:16 pmMDW - SJU
1 stop18h 16mMultiple Airlines
Tue 12/95:00 pmSJU - MDW
2 stops17h 46mMultiple Airlines
Deal found 11/4$221
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/197:34 pmORD - SJU
2 stops22h 53mMultiple Airlines
Sun 11/232:25 amSJU - ORD
1 stop10h 46mMultiple Airlines
Deal found 11/5$222
This Orbitz deal was found by Cheapflights users on 11/3. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/175:05 amORD - SJU
1 stop8h 14mMultiple Airlines
Thu 11/2011:55 amSJU - ORD
2 stops21h 48mMultiple Airlines
Deal found 11/3$223

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 November 6, 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

Mon 1/26

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 1/30

8:35 am-11:57 am

Nonstop5h 22m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

3:35 pm-12:36 am

1 stop7h 01m

San Juan Luis Munoz Marin Intl

Fri 1/30

2:05 am-9:40 am

1 stop9h 35m

$262

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 2/1

8:52 am-5:25 pm

1 stop6h 33m

Punta Cana

Fri 2/6

5:20 pm-11:39 pm

1 stop8h 19m

$278

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/26

2:20 pm-12:35 am

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Fri 1/30

9:05 am-2:45 pm

1 stop7h 40m

$287

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/5

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Thu 1/15

8:35 am-11:57 am

Nonstop5h 22m

$292

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 12/7

7:52 am-2:22 pm

Nonstop4h 30m

Punta Cana

Sun 12/14

5:20 pm-11:43 pm

1 stop8h 23m

$298

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 12/5

9:30 am-4:02 pm

Nonstop4h 32m

Punta Cana

Tue 12/16

5:20 pm-11:43 pm

1 stop8h 23m

$298

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/4

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Tue 1/13

2:05 am-9:40 am

1 stop9h 35m

$298

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 1/23

6:00 am-5:25 pm

1 stop9h 25m

Punta Cana

Fri 1/30

5:20 pm-11:39 pm

1 stop8h 19m

$303

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 12/8

9:30 am-4:02 pm

Nonstop4h 32m

Punta Cana

Mon 12/15

2:55 pm-6:08 pm

Nonstop5h 13m

$306

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

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, February 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 $188). 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 6, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 22% 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 16, 2024.

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. Sunday mornings 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 November 6, 2025.

The most flights from CHI to zzEPX are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 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 November 6, 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
8,001 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

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
8,001 reviews
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

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
9,007 reviews
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

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
11,040 reviews
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

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
8,122 reviews
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

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
5.8
Fair
3,115 reviews
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

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 $216, United Airlines can have you in Caribbean Islands from Chicago in 4h 40m. 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?

    $102 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 United Airlines and Delta, with prices starting from $114 and $114, 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 American Airlines (94%), Alaska Airlines (89%) or Spirit Airlines (72%) 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 $680, our data indicates the cheapest price to be $113. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $138.

  • 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, February 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 $188). 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$451FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$376FlexibilityNo cancel feeOn-time65%
DeltaCheapest$186Average$634FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$226Average$612FlexibilityNo cancel feeOn-time69%
ArajetCheapest$233Average$330FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$261Average$484FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$335Average$612FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$337Average$630FlexibilityNo cancel feeOn-time71%

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