HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$98+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 July 31, 2025.

Round-trip from

$216
(FlightHub)

One-way from

$96
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$377
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. 12% potential increase in price ($54 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 July 2025
Search Deals

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 July 31, 2025.

This FlightHub deal was found by Cheapflights users on 7/31. 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.
Sat 8/3011:36 amORD - STT
2 stops25h 12mSpirit Airlines
Sat 9/610:49 amSTT - ORD
1 stop7h 50mSpirit Airlines
Deal found 7/31$216
This Booking.com deal was found by Cheapflights users on 7/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/106:23 pmORD - SJU
Nonstop4h 43mSpirit Airlines
Thu 8/147:40 pmSJU - ORD
Nonstop5h 03mSpirit Airlines
Deal found 7/30$224
This CheapOair deal was found by Cheapflights users on 7/29. 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.
Sat 8/308:47 pmORD - SJU
1 stop17h 20mMultiple Airlines
Fri 9/53:39 amSJU - ORD
1 stop12h 38mMultiple Airlines
Deal found 7/29$227
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/3010:51 amMDW - SJU
1 stop7h 27mFrontier
Fri 9/53:39 amSJU - MDW
1 stop7h 12mFrontier
Deal found 7/29$235
This Frontier deal was found by Cheapflights users on 7/30. 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.
Sat 8/99:08 amORD - SJU
1 stop10h 21mFrontier
Wed 8/133:29 amSJU - ORD
1 stop12h 58mFrontier
Deal found 7/30$258
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
Tue 10/73:19 pmPUJ - ORD
1 stop8h 29mSpirit Airlines
Deal found 7/29$298
This Priceline deal was found by Cheapflights users on 7/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/136:45 amORD - PUJ
Nonstop4h 40mFrontier
Sun 8/175:45 pmPUJ - ORD
Nonstop5h 08mFrontier
Deal found 7/29$306
This CheapOair deal was found by Cheapflights users on 7/30. 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 8/136:45 amORD - PUJ
Nonstop4h 40mMultiple Airlines
Sat 8/164:05 pmPUJ - ORD
1 stop8h 54mMultiple Airlines
Deal found 7/30$311
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Mon 8/188:35 amORD - PUJ
Nonstop4h 40mAmerican Airlines
Wed 8/273:30 pmPUJ - ORD
Nonstop5h 00mAmerican Airlines
Deal found 7/31$327
This Booking.com deal was found by Cheapflights users on 7/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/235:05 amORD - AUA
1 stop8h 35mSpirit Airlines
Sat 8/303:45 pmAUA - ORD
1 stop9h 14mSpirit Airlines
Deal found 7/30$328
This Frontier deal was found by Cheapflights users on 7/29. 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.
Sat 12/65:10 amORD - AUA
1 stop8h 19mFrontier
Sat 12/134:40 pmAUA - ORD
1 stop20h 06mFrontier
Deal found 7/29$333
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:00 amORD - PUJ
1 stop6h 23mDelta
Fri 11/142:03 pmPUJ - ORD
1 stop9h 09mDelta
Deal found 7/29$343

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 July 31, 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

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 8/30

11:36 am-1:48 pm

2 stops25h 12m

Saint Thomas Island Cyril E King

Sat 9/6

10:49 am-5:39 pm

1 stop7h 50m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/10

6:23 pm-12:06 am

Nonstop4h 43m

San Juan Luis Munoz Marin Intl

Thu 8/14

7:40 pm-11:43 pm

Nonstop5h 03m

$224

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/30

8:47 pm-3:07 pm

1 stop17h 20m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-3:17 pm

1 stop12h 38m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/30

10:51 am-7:18 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-9:51 am

1 stop7h 12m

$235

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/16

9:08 am-8:29 pm

1 stop10h 21m

San Juan Luis Munoz Marin Intl

Wed 8/20

8:13 pm-6:41 pm

1 stop23h 28m

$239

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 10/4

5:05 am-2:14 pm

1 stop8h 09m

Punta Cana

Tue 10/7

3:19 pm-10:48 pm

1 stop8h 29m

$298

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 8/13

6:45 am-12:25 pm

Nonstop4h 40m

Punta Cana

Sun 8/17

5:45 pm-9:53 pm

Nonstop5h 08m

$306

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 8/13

6:45 am-12:25 pm

Nonstop4h 40m

Punta Cana

Sat 8/16

4:05 pm-11:59 pm

1 stop8h 54m

$311

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 8/18

8:35 am-2:15 pm

Nonstop4h 40m

Punta Cana

Wed 8/27

3:30 pm-7:30 pm

Nonstop5h 00m

$327

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

Sat 8/23

5:05 am-2:40 pm

1 stop8h 35m

Oranjestad Reina Beatrix

Sat 8/30

3:45 pm-11:59 pm

1 stop9h 14m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 60 results
1
2
3
...
6

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 $254). Flying from Chicago to Caribbean Islands in June is currently the most expensive (average of $339). 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 July 31, 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 July 31, 2025.

The most flights from CHI to zzEPX are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 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 July 31, 2025.
Read through reviews of airlines operating flights from Chicago to Caribbean Islands, such as Delta, Southwest, and Copa 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
8.0
Very good
7,981 reviews

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Southwest
8.0
Very good
4,246 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Copa Airlines
7.5
Good
1,493 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,900 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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?

    $96 is the cheapest one-way deal found within the past few days, from Arajet. You may also be able to find cheap deals on Spirit Airlines and Frontier, with prices starting from $102 and $117, 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 Midway - San Juan Luis Munoz Marin Intl 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 Air Canada (83%), United Airlines (83%) or Air New Zealand (83%) 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 $575, our data indicates the cheapest price to be $117. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $190.

  • 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 June is currently the most expensive (average of $339). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to LaGuardia flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Newark flights
O'Hare Intl to Cancún flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Seattle flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Denver flights
O'Hare Intl to Boston flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Orlando flights
Midway to Las Vegas flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
Midway to LaGuardia flights
Midway to Newark flights
O'Hare Intl to San Francisco flights
O'Hare Intl to San Diego flights
O'Hare Intl to Ontario flights
Midway to Cancún flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Dulles Intl flights
Midway to John F Kennedy Intl flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Atlanta flights
St. Louis to Las Vegas flights
O'Hare Intl to Santa Ana flights
Midway to Miami flights
O'Hare Intl to Nashville flights
O'Hare Intl to Portland flights
O'Hare Intl to Tampa flights
O'Hare Intl to Austin flights
O'Hare Intl to Cozumel flights
O'Hare Intl to Pearson Intl flights
Midway to Orlando flights
O'Hare Intl to Baltimore flights
St. Louis to Seattle flights
O'Hare Intl to Hobby flights
Midway to Mexico City flights
O'Hare Intl to George Bush Intcntl flights
Midway to Dallas/Fort Worth flights
Midway to Denver flights
Midway to Seattle flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Raleigh flights
Midway to Atlanta flights
Midway to San Francisco flights

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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$357FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$379FlexibilityNo cancel feeOn-time65%
DeltaCheapest$190Average$619FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$193Average$476FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$226Average$627FlexibilityNo cancel feeOn-time69%
ArajetCheapest$235Average$315FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$261Average$481FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$335Average$750FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$346Average$655FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$352Average$648FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.