HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$83+ 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 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Caribbean 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

Keep the following information in mind while searching for Chicago to Caribbean flight deals. Data was last updated February 20, 2025.

Round-trip from

$168
(Booking.com)

One-way from

$83
(Mytrip)

Popular in

December

Cheapest in

April

Average price

$372

Good round-trip deal

$283 or less

Good one-way deal

$170 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. 15% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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

Find 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 February 20, 2025.

This Booking.com deal was found by Cheapflights users on 2/20. 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.
Mon 3/105:05 amORD - SJU
1 stop18h 10mMultiple Airlines
Sat 3/156:00 amSJU - ORD
Nonstop5h 36mMultiple Airlines
Deal found 2/20$168
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Wed 3/54:20 pmMDW - SJU
1 stop26h 50mFrontier
Tue 3/116:00 amSJU - MDW
1 stop10h 32mFrontier
Deal found 2/19$168
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 5/1410:00 amORD - SJU
Nonstop4h 51mSpirit Airlines
Fri 5/304:46 pmSJU - ORD
Nonstop5h 04mSpirit Airlines
Deal found 2/20$169
This Frontier deal was found by Cheapflights users on 2/20. 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 3/81:30 pmORD - SJU
1 stop10h 10mFrontier
Thu 3/135:45 amSJU - ORD
1 stop14h 09mFrontier
Deal found 2/20$171
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/199:08 pmORD - STT
1 stop10h 47mSpirit Airlines
Tue 3/259:50 amSTT - ORD
1 stop10h 06mSpirit Airlines
Deal found 2/19$262
This Delta deal was found by Cheapflights users on 2/20. 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.
Mon 3/1011:30 amORD - SJU
1 stop7h 40mDelta
Wed 3/192:42 pmSJU - ORD
1 stop7h 16mDelta
Deal found 2/20$271
This Delta deal was found by Cheapflights users on 2/20. 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.
Tue 3/1112:51 pmMDW - SJU
1 stop9h 16mDelta
Tue 3/1812:54 pmSJU - MDW
1 stop10h 29mDelta
Deal found 2/20$271
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 2/286:35 pmORD - SJU
1 stop9h 37mUnited Airlines
Sat 3/12:05 amSJU - ORD
1 stop9h 00mUnited Airlines
Deal found 2/20$296
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 4/19:08 pmORD - PUJ
1 stop14h 09mMultiple Airlines
Mon 4/711:33 amPUJ - ORD
2 stops29h 36mMultiple Airlines
Deal found 2/20$304
This Frontier deal was found by Cheapflights users on 2/20. 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 5/286:00 amORD - PUJ
2 stops16h 54mFrontier
Tue 6/33:05 pmPUJ - ORD
1 stop10h 03mFrontier
Deal found 2/20$305
This Booking.com deal was found by Cheapflights users on 2/19. 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 5/2512:46 pmMDW - PUJ
2 stops19h 05mFrontier
Wed 5/283:05 pmPUJ - MDW
1 stop9h 50mFrontier
Deal found 2/19$309
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/246:38 pmMDW - PUJ
2 stops19h 04mMultiple Airlines
Tue 4/11:14 pmPUJ - MDW
1 stop11h 10mMultiple Airlines
Deal found 2/19$319

Find flights from Chicago to Caribbean within your budget

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 February 20, 2025.

Fly from

Chicago

Fly to

Caribbean

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/10

5:05 am-12:15 am

1 stop18h 10m

San Juan Luis Munoz Marin Intl

Sat 3/15

6:00 am-10:36 am

Nonstop5h 36m

$168

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 3/5

4:20 pm-9:10 pm

1 stop26h 50m

San Juan Luis Munoz Marin Intl

Tue 3/11

6:00 am-3:32 pm

1 stop10h 32m

$168

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 5/14

10:00 am-3:51 pm

Nonstop4h 51m

San Juan Luis Munoz Marin Intl

Fri 5/30

4:46 pm-8:50 pm

Nonstop5h 04m

$169

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 3/8

1:30 pm-1:40 am

1 stop10h 10m

San Juan Luis Munoz Marin Intl

Thu 3/13

5:45 am-6:54 pm

1 stop14h 09m

$171

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 3/19

9:08 pm-8:55 am

1 stop10h 47m

Saint Thomas Island Cyril E King

Tue 3/25

9:50 am-6:56 pm

1 stop10h 06m

$262

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/10

11:30 am-8:10 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Wed 3/19

2:42 pm-8:58 pm

1 stop7h 16m

$271

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 3/11

12:51 pm-11:07 pm

1 stop9h 16m

San Juan Luis Munoz Marin Intl

Tue 3/18

12:54 pm-10:23 pm

1 stop10h 29m

$271

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 4/1

9:08 pm-12:17 pm

1 stop14h 09m

Punta Cana

Mon 4/7

11:33 am-4:09 pm

2 stops29h 36m

$304

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 5/28

6:00 am-11:54 pm

2 stops16h 54m

Punta Cana

Tue 6/3

3:05 pm-12:08 am

1 stop10h 03m

$305

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 3/18

5:10 am-2:42 pm

1 stop8h 32m

Punta Cana

Tue 3/25

3:47 pm-11:59 pm

1 stop9h 12m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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

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.

Travel insights for flights from Chicago to Caribbean

Get recent, data-driven insights about flights from Chicago to Caribbean including ideal travel times, pricing trends, and more.

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 $254). Flying from Chicago to Caribbean in March is currently the most expensive (average of $363). 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 February 20, 2025.

When flying from Chicago to Caribbean, 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

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 February 20, 2025.

The most flights from CHI to 0CB are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, 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

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 February 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

SWISS
7.5
Good
1,568 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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.

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

    $83 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 Frontier and United Airlines, with prices starting from $84 and $136, 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 (85%), Alaska Airlines (85%) and Spirit Airlines (81%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? While on average our users pay $792, our data indicates the cheapest price to be $84. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $126.

  • 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 $254). Flying from Chicago to Caribbean in March is currently the most expensive (average of $363). 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

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Miami flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Seattle flights
O'Hare Intl to Orlando flights
O'Hare Intl to Dallas/Fort Worth flights
Midway to Las Vegas flights
O'Hare Intl to Denver flights
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to San Francisco flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
O'Hare Intl to Heathrow flights
Midway to Cancún flights
O'Hare Intl to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Charles de Gaulle flights
O'Hare Intl to Boston flights
O'Hare Intl to San Diego flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Tampa flights
O'Hare Intl to Narita flights
O'Hare Intl to Austin flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Nashville flights
O'Hare Intl to Haneda flights
O'Hare Intl to Athens flights
O'Hare Intl to Honolulu flights
Midway to Newark flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Dublin flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Baltimore flights
Midway to LaGuardia flights
Midway to John F Kennedy Intl flights
Midway to Sky Harbor Intl flights
Midway to Fort Lauderdale flights
Midway to Miami flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Hobby flights
O'Hare Intl to Punta Cana flights
St. Louis to Seattle flights

Top 10 airlines flying from Chicago to Caribbean

Discover the top 10 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$366FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$151Average$347FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$226Average$638FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$226Average$524FlexibilityNo cancel feeOn-time70%
JetBlueCheapest$293Average$509FlexibilityNo cancel feeOn-time62%
DeltaCheapest$293Average$671FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$323Average$633FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$332Average$678FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$335Average$779FlexibilityNo cancel feeOn-time67%
AviancaCheapest$1,422Average$1,422FlexibilityNo cancel feeOn-time71%
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.