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$72+ Cheap flights from Chicago (CHI) to Caribbean

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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Chicago to Caribbean

Cheapest flights from Chicago to Caribbean
Explore the most affordable flight options available from Chicago to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Priceline deal was found by Cheapflights users on 12/10. 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 12/177:00 amORD - SJU
1 stop9h 53mMultiple Airlines
Wed 12/248:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Deal found 12/10$201
This Frontier deal was found by Cheapflights users on 12/11. 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.
Wed 12/3111:23 amORD - SJU
1 stop7h 04mFrontier
Thu 1/154:35 pmSJU - ORD
1 stop8h 09mFrontier
Deal found 12/11$205
This Trip.com deal was found by Cheapflights users on 12/10. 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.
Sat 12/137:00 amORD - SJU
1 stop9h 53mMultiple Airlines
Thu 12/185:09 pmSJU - ORD
1 stop17h 43mMultiple Airlines
Deal found 12/10$206
This WAYA deal was found by Cheapflights users on 12/10. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:15 pmORD - SJU
1 stop8h 35mMultiple Airlines
Fri 1/95:18 pmSJU - ORD
1 stop8h 28mMultiple Airlines
Deal found 12/10$208
This Trip.com deal was found by Cheapflights users on 12/11. 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.
Sat 12/137:00 amORD - SJU
1 stop9h 53mJetBlue
Mon 12/151:45 pmSJU - ORD
1 stop10h 07mJetBlue
Deal found 12/11$215
This Trip.com deal was found by Cheapflights users on 12/10. 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.
Fri 12/127:00 amORD - SJU
1 stop9h 52mJetBlue
Mon 12/151:45 pmSJU - ORD
1 stop10h 07mJetBlue
Deal found 12/10$220
This Trip.com deal was found by Cheapflights users on 12/11. 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.
Sat 12/137:00 amORD - SJU
1 stop9h 53mJetBlue
Sun 12/141:45 pmSJU - ORD
1 stop10h 07mJetBlue
Deal found 12/11$221
This Priceline deal was found by Cheapflights users on 12/11. 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.
Tue 12/1611:25 amORD - SJU
1 stop10h 29mMultiple Airlines
Tue 12/236:25 amSJU - ORD
1 stop7h 40mMultiple Airlines
Deal found 12/11$223
This CheapOair deal was found by Cheapflights users on 12/10. 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 12/10$224
This Frontier deal was found by Cheapflights users on 12/9. 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 12/301:27 pmORD - SJU
1 stop15h 07mFrontier
Fri 1/97:10 amSJU - ORD
1 stop11h 57mFrontier
Deal found 12/9$227
This Trip.com deal was found by Cheapflights users on 12/11. 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.
Sat 12/137:00 amORD - SJU
1 stop9h 53mMultiple Airlines
Mon 12/158:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Deal found 12/11$228
This CheapOair deal was found by Cheapflights users on 12/10. 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.
Mon 12/153:10 pmMDW - SJU
1 stop9h 40mFrontier
Mon 12/224:21 pmSJU - MDW
1 stop7h 51mFrontier
Deal found 12/10$246

Find flight deals from Chicago to Caribbean

Keep the following information in mind while searching for Chicago to Caribbean flight deals. Data was last updated December 12, 2025.

Round-trip from

$199
(Priceline)

One-way from

$72
(Expedia)

Popular in

December

Cheapest in

April

Average price

$592

Good round-trip deal

$303 or less

Good one-way deal

$153 or less
From Chicago (CHI) to Caribbean
Search Deals
One-way flight from Chicago (CHI) to Caribbean
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Caribbean.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Caribbean.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Caribbean 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 12, 2025.
Use the filters below to find and compare flights from Chicago to Caribbean that are best for you.

Fly from

Chicago

Fly to

Caribbean

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 2/28

8:00 am-2:53 am

1 stop16h 53m

San Juan Luis Munoz Marin Intl

Sat 3/7

12:07 pm-11:32 pm

1 stop13h 25m

$201

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/27

12:41 pm-11:44 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Sat 3/7

5:10 am-11:58 am

1 stop8h 48m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/18

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Fri 1/23

11:06 am-7:36 pm

1 stop10h 30m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 6/2

3:15 pm-1:59 am

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Tue 6/9

12:30 pm-7:26 pm

1 stop7h 56m

$214

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 2/6

1:00 pm-3:26 pm

1 stop24h 26m

San Juan Luis Munoz Marin Intl

Sat 2/14

8:02 pm-2:26 pm

1 stop20h 24m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

6:04 am-4:56 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

Sun 3/1

5:10 am-11:48 am

1 stop8h 38m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/31

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Mon 2/2

11:06 am-7:36 pm

1 stop10h 30m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 3/11

12:41 pm-9:31 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Thu 3/19

1:30 am-10:05 am

1 stop9h 35m

$220

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 3/20

10:56 am-11:23 pm

1 stop11h 27m

San Juan Luis Munoz Marin Intl

Tue 3/24

1:30 am-10:05 am

1 stop9h 35m

$220

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/25

3:15 pm-12:40 am

1 stop7h 25m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:10 am-11:35 am

1 stop7h 25m

$225

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

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

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

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $127). Flying from Chicago to Caribbean 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 CB?

Find hourly flight availability from Chicago to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

One of the essential ways to save on airfare from Chicago to Caribbean is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 21% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Caribbean. Price data was last updated on December 16, 2024.

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

Weekly flight availability from Chicago to Caribbean

Explore weekly flight availability from Chicago to Caribbean. 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 12, 2025.

The most flights from CHI to 0CB are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 on average).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated December 12, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Chicago to Caribbean. 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
8,008 reviews

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.3

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
8,008 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.3

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
9,095 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.3

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
11,050 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.3

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
8,179 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.3

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
3,084 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.3

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. 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?

    There are many flights that can get you from Chicago to Caribbean in 7h 25m. Fly via Frontier, JetBlue, or Southwest to get the fastest option. The distance between Chicago and Caribbean is about 2057 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to Caribbean 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 $82 and $90, respectively.

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

    The most popular flight routes from Chicago to Caribbean are Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago O'Hare Intl - Punta Cana and Chicago Midway - San Juan Luis Munoz Marin Intl.

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

    The top 3 most reliable airlines when flying from Chicago to Caribbean are American Airlines (79%), Air Canada (77%) and United Airlines (77%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? While on average our users pay $566, 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 $122.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Caribbean 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?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $127). Flying from Chicago to Caribbean 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.

See more FAQs

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Alternative routes for Chicago to Caribbean

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

Discover the top 9 airlines that operate flights from Chicago to Caribbean. 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 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$107Average$451FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$362FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$147Average$445FlexibilityNo cancel feeOn-time62%
DeltaCheapest$186Average$626FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$215Average$607FlexibilityNo cancel feeOn-time69%
ArajetCheapest$236Average$334FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$335Average$598FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$337Average$633FlexibilityNo cancel feeOn-time71%

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