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$95+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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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 October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2712:55 pmORD - SJU
1 stop11h 59mMultiple Airlines
Thu 12/410:42 amSJU - ORD
1 stop9h 54mMultiple Airlines
Deal found 10/28$212
This Frontier deal was found by Cheapflights users on 10/29. 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.
Mon 11/246:15 pmORD - SJU
1 stop6h 39mFrontier
Thu 11/274:05 pmSJU - ORD
1 stop10h 03mFrontier
Deal found 10/29$215
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/278:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Fri 12/58:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 10/28$217
This CheapOair deal was found by Cheapflights users on 10/27. 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.
Mon 12/85:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Mon 12/158:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 10/27$218
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.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 10/28$219
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Mon 11/176:40 amORD - SJU
2 stops30h 02mMultiple Airlines
Fri 11/215:19 pmSJU - ORD
1 stop17h 58mMultiple Airlines
Deal found 10/27$220
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/274:00 pmMDW - SJU
2 stops39h 27mFrontier
Thu 12/410:42 amSJU - MDW
1 stop13h 11mFrontier
Deal found 10/28$221
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Mon 11/178:00 amORD - SJU
Nonstop4h 36mMultiple Airlines
Thu 11/209:30 pmSJU - ORD
1 stop15h 05mMultiple Airlines
Deal found 10/27$222
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/82:20 pmORD - SJU
Nonstop4h 40mUnited Airlines
Wed 12/102:05 amSJU - ORD
1 stop9h 43mUnited Airlines
Deal found 10/28$223
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/196:40 amORD - SJU
1 stop9h 14mFrontier
Fri 11/212:25 amSJU - ORD
1 stop10h 46mFrontier
Deal found 10/28$225
This Delta deal was found by Cheapflights users on 10/27. 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 12/86:00 amMDW - SJU
1 stop6h 14mDelta
Wed 12/101:57 pmSJU - MDW
1 stop11h 50mDelta
Deal found 10/27$227
This Booking.com deal was found by Cheapflights users on 10/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/152:05 pmMDW - SJU
1 stop16h 40mFrontier
Fri 11/213:59 amSJU - MDW
1 stop15h 08mFrontier
Deal found 10/26$230

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 October 29, 2025.

Round-trip from

$209
(Frontier)

One-way from

$95
(Priceline)

Popular in

December

Cheapest in

April

Average price

$360

Good round-trip deal

$350 or less

Good one-way deal

$191 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. 7% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 29, 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

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/12

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

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

5:33 am-2:30 pm

1 stop6h 57m

San Juan Luis Munoz Marin Intl

Wed 1/28

7:00 am-5:45 pm

1 stop12h 45m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

6:20 pm-6:11 am

1 stop9h 51m

San Juan Luis Munoz Marin Intl

Fri 1/30

8:10 am-2:25 pm

1 stop8h 15m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/21

1:55 pm-11:59 pm

1 stop8h 04m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:27 pm-11:57 pm

1 stop7h 30m

$227

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Mon 2/16

9:30 am-4:18 pm

Nonstop4h 48m

Saint Thomas Island Cyril E King

Thu 2/19

3:05 pm-6:45 pm

Nonstop5h 40m

$242

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 2/4

9:52 am-8:57 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Sat 2/14

7:00 am-5:37 pm

1 stop12h 37m

$252

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/23

10:53 am-11:44 pm

1 stop10h 51m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:55 pm-10:26 pm

1 stop8h 31m

$252

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 1/23

2:05 am-9:40 am

1 stop9h 35m

$258

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/21

1:45 pm-12:35 am

2 stops8h 50m

San Juan Luis Munoz Marin Intl

Wed 1/28

12:10 pm-9:50 pm

1 stop11h 40m

$277

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/21

6:50 am-7:05 pm

2 stops10h 15m

San Juan Luis Munoz Marin Intl

Sat 1/31

5:30 am-2:45 pm

2 stops11h 15m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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, February 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 $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 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 October 29, 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 22% 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. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 29, 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
7,992 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,992 reviews
Delta
7.9
Good
7,992 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,999 reviews
Delta
7.9
Good
7,992 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,992 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Spirit Airlines
6.3
Okay
8,114 reviews
Delta
7.9
Good
7,992 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Frontier
5.8
Fair
3,124 reviews
Delta
7.9
Good
7,992 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 4h 40m. Fly via United Airlines, Delta, or Southwest to get the fastest option. The distance between Chicago and Caribbean is about 2073 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?

    $109 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Delta and Southwest, with prices starting from $114 and $114, 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 (91%), Alaska Airlines (82%) and Spirit Airlines (78%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? While on average our users pay $813, our data indicates the cheapest price to be $124. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $213.

  • 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, February 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 $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.

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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$450FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$385FlexibilityNo cancel feeOn-time65%
DeltaCheapest$186Average$631FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$226Average$613FlexibilityNo cancel feeOn-time69%
ArajetCheapest$233Average$331FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$261Average$470FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$337Average$643FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$380Average$662FlexibilityNo cancel feeOn-time63%

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