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$106+ 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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
1 adult, Economy
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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 July 28, 2025.

Round-trip from

$213
(FlightHub)

One-way from

$106
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$377

Good round-trip deal

$280 or less

Good one-way deal

$126 or less
From Chicago (CHI) to Caribbean
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One-way flight from Chicago (CHI) to Caribbean
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Highest demand for flights based on searches. 12% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Caribbean.
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Price to beat on a one-way flight from Chicago (CHI) to Caribbean.
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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 July 28, 2025.

This FlightHub deal was found by Cheapflights users on 7/26. 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.
Tue 8/198:12 pmORD - STT
2 stops16h 36mSpirit Airlines
Tue 8/262:43 pmSTT - ORD
1 stop8h 39mSpirit Airlines
Deal found 7/26$213
This Cheapflightsfares deal was found by Cheapflights users on 7/25. 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.
Sun 8/3112:55 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Thu 9/1811:59 amSJU - ORD
1 stop6h 40mSpirit Airlines
Deal found 7/25$229
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/74:37 pmORD - SJU
1 stop9h 02mMultiple Airlines
Thu 8/148:00 pmSJU - ORD
1 stop14h 22mMultiple Airlines
Deal found 7/27$232
This eDestinos deal was found by Cheapflights users on 7/26. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/317:46 pmORD - SJU
1 stop22h 22mFrontier
Sat 9/64:42 pmSJU - ORD
1 stop28h 02mFrontier
Deal found 7/26$234
This Cheapflightsfares deal was found by Cheapflights users on 7/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:15 amMDW - SJU
1 stop6h 56mFrontier
Fri 9/263:39 amSJU - MDW
1 stop7h 12mFrontier
Deal found 7/27$236
This FlightHub deal was found by Cheapflights users on 7/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/65:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
Sat 9/133:19 pmPUJ - ORD
1 stop8h 29mSpirit Airlines
Deal found 7/27$298
This Frontier deal was found by Cheapflights users on 7/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/296:45 amORD - PUJ
Nonstop4h 40mFrontier
Wed 8/65:08 pmPUJ - ORD
Nonstop5h 08mFrontier
Deal found 7/27$301
This CheapOair deal was found by Cheapflights users on 7/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/126:45 amORD - PUJ
Nonstop4h 40mMultiple Airlines
Tue 8/1912:40 pmPUJ - ORD
1 stop10h 42mMultiple Airlines
Deal found 7/27$308
This CheapOair deal was found by Cheapflights users on 7/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:05 amORD - AUA
1 stop8h 35mSpirit Airlines
Sat 10/113:45 pmAUA - ORD
1 stop9h 00mSpirit Airlines
Deal found 7/28$330
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Sat 8/237:05 pmORD - PUJ
1 stop16h 45mAmerican Airlines
Wed 8/273:30 pmPUJ - ORD
Nonstop5h 00mAmerican Airlines
Deal found 7/26$333
This Delta deal was found by Cheapflights users on 7/28. 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.
Sun 11/96:00 amORD - PUJ
1 stop7h 20mDelta
Fri 11/142:03 pmPUJ - ORD
1 stop9h 09mDelta
Deal found 7/28$343
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:00 amMDW - PUJ
1 stop6h 23mDelta
Fri 11/143:50 pmPUJ - MDW
1 stop7h 54mDelta
Deal found 7/27$343

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 July 28, 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

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 8/19

8:12 pm-1:48 pm

2 stops16h 36m

Saint Thomas Island Cyril E King

Tue 8/26

2:43 pm-10:22 pm

1 stop8h 39m

$213

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/31

12:55 pm-6:40 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Thu 9/18

11:59 am-5:39 pm

1 stop6h 40m

$229

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 8/7

4:37 pm-2:39 am

1 stop9h 02m

San Juan Luis Munoz Marin Intl

Thu 8/14

8:00 pm-9:22 am

1 stop14h 22m

$232

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/31

7:46 pm-7:08 pm

1 stop22h 22m

San Juan Luis Munoz Marin Intl

Sat 9/6

4:42 pm-7:44 pm

1 stop28h 02m

$234

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/13

6:15 am-2:11 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Fri 9/26

3:39 am-9:51 am

1 stop7h 12m

$236

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 9/6

5:05 am-2:14 pm

1 stop8h 09m

Punta Cana

Sat 9/13

3:19 pm-10:48 pm

1 stop8h 29m

$298

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 8/10

6:45 am-12:25 pm

Nonstop4h 40m

Punta Cana

Sat 8/23

12:31 pm-11:59 pm

2 stops12h 28m

$302

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 8/9

6:45 am-12:25 pm

Nonstop4h 40m

Punta Cana

Wed 8/13

5:08 pm-9:16 pm

Nonstop5h 08m

$309

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

Sat 10/4

5:05 am-2:40 pm

1 stop8h 35m

Oranjestad Reina Beatrix

Sat 10/11

3:45 pm-11:45 pm

1 stop9h 00m

$330

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 8/23

7:05 pm-12:50 pm

1 stop16h 45m

Punta Cana

Wed 8/27

3:30 pm-7:30 pm

Nonstop5h 00m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

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 $254). Flying from Chicago to Caribbean 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 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 July 28, 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 July 28, 2025.

The most flights from CHI to 0CB are scheduled on a Saturday (11 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 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 July 28, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Delta 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,237 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,971 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Copa Airlines
7.5
Good
1,493 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,886 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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?

    $106 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 American Airlines, with prices starting from $106 and $155, 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 Midway - San Juan Luis Munoz Marin Intl and Chicago O'Hare Intl - Montego Bay Sangster Intl.

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

    The top 3 most reliable airlines when flying from Chicago to Caribbean are Air Canada (83%), United Airlines (83%) and Air New Zealand (83%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? 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 $215.

  • 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 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

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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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Midway to Orlando 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 July 28, 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%

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