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$66+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 January 28, 2026.

This Rumbo deal was found by Cheapflights users on 1/26. 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 Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/27:44 am
ORD
-
SJU
1 stop9h 39m
JetBlue
Wed 2/119:25 am
SJU
-
ORD
1 stop12h 06m
JetBlue
Deal found 1/26$185
This Expedia deal was found by Cheapflights users on 1/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/212:17 pm
ORD
-
SJU
Nonstop4h 32m
Multiple Airlines
Mon 2/911:15 am
SJU
-
ORD
1 stop30h 37m
Multiple Airlines
Deal found 1/26$186
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Tue 2/247:00 am
ORD
-
SJU
1 stop6h 31m
Spirit Airlines
Fri 3/612:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/27$187
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Tue 2/247:00 am
ORD
-
SJU
1 stop6h 31m
Multiple Airlines
Wed 3/43:53 am
SJU
-
ORD
1 stop8h 53m
Multiple Airlines
Deal found 1/27$188
This Mytrip deal was found by Cheapflights users on 1/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/312:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Tue 2/101:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Deal found 1/27$189
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/233:50 pm
ORD
-
SJU
1 stop6h 53m
Multiple Airlines
Thu 3/121:29 am
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Deal found 1/27$190
This JetBlue deal was found by Cheapflights users on 1/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2310:00 am
ORD
-
SJU
1 stop10h 53m
JetBlue
Tue 2/245:10 am
SJU
-
ORD
1 stop8h 49m
JetBlue
Deal found 1/27$191
This JetBlue deal was found by Cheapflights users on 1/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:15 am
ORD
-
SJU
1 stop9h 25m
JetBlue
Thu 4/911:00 am
SJU
-
ORD
1 stop11h 33m
JetBlue
Deal found 1/27$192
This Priceline deal was found by Cheapflights users on 1/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1110:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Mon 4/131:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/26$193
This CheapOair deal was found by Cheapflights users on 1/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:14 am
MDW
-
SJU
1 stop15h 47m
Frontier
Sat 4/258:00 am
SJU
-
MDW
1 stop9h 13m
Frontier
Deal found 1/26$193
This Orbitz deal was found by Cheapflights users on 1/25. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1812:22 pm
ORD
-
SJU
Nonstop4h 31m
Multiple Airlines
Tue 3/243:26 am
SJU
-
ORD
1 stop8h 59m
Multiple Airlines
Deal found 1/25$195
This CheapOair deal was found by Cheapflights users on 1/27. 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.
Sat 4/114:21 pm
ORD
-
SJU
1 stop8h 40m
Multiple Airlines
Mon 4/131:29 am
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Deal found 1/27$196

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 January 28, 2026.

Round-trip from

$185
(Rumbo)

One-way from

$66
(Expedia)

Popular in

December

Cheapest in

April

Average price

$358

Good round-trip deal

$303 or less

Good one-way deal

$128 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. 10% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 28, 2026.
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 2/16

10:00 am-10:53 pm

1 stop10h 53m

San Juan Luis Munoz Marin Intl

Fri 2/27

1:44 pm-10:59 pm

1 stop11h 15m

$191

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

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 2/19

10:00 am-10:53 pm

1 stop10h 53m

San Juan Luis Munoz Marin Intl

Wed 2/25

5:10 am-12:04 pm

1 stop8h 54m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 4/9

10:00 am-10:01 pm

1 stop11h 01m

San Juan Luis Munoz Marin Intl

Fri 4/17

11:59 pm-7:41 am

1 stop8h 42m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 5/20

3:15 pm-2:07 am

1 stop9h 52m

San Juan Luis Munoz Marin Intl

Tue 5/26

3:30 am-2:20 pm

1 stop11h 50m

$217

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 5/1

12:22 pm-5:54 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Tue 5/5

12:22 pm-4:37 pm

Nonstop5h 15m

$219

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/7

8:31 am-6:30 pm

1 stop8h 59m

San Juan Luis Munoz Marin Intl

Mon 5/11

11:59 pm-9:48 am

1 stop10h 49m

$221

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 2/25

12:59 pm-12:29 am

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Mon 3/9

4:15 am-11:48 am

1 stop8h 33m

$229

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 4/4

7:45 am-6:40 pm

1 stop9h 55m

San Juan Luis Munoz Marin Intl

Tue 4/14

11:25 pm-8:51 am

1 stop10h 26m

$229

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 3/19

11:00 am-10:09 pm

1 stop10h 09m

San Juan Luis Munoz Marin Intl

Wed 3/25

3:26 am-11:25 am

1 stop8h 59m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 60 results
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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.

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 $126). Flying from Chicago to Caribbean in December is currently the most expensive (average of $195). 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 January 28, 2026.

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 evening could potentially save you up to 40% 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 January 24, 2026.

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 at noon 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 January 28, 2026.

The most flights from CHI to 0CB are scheduled on a Monday (11 on average). You will have fewer flight options on Thursday, 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 January 28, 2026.
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
8,120 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

Food

7.2

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
8,120 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

Food

7.2

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
9,206 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

Food

7.2

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
11,198 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

Food

7.2

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
8,384 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

Food

7.2

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
5.7
Fair
3,056 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

Food

7.2

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 4h 45m. Fly via JetBlue, WorldTicket, or Delta to get the fastest option. The distance between Chicago and Caribbean is about 1982 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?

    $82 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Frontier and Spirit Airlines, with prices starting from $83 and $87, 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 United Airlines (81%), Air New Zealand (81%) and Air Canada (80%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? While on average our users pay $527, our data indicates the cheapest price to be $89. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $106.

  • 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 $126). Flying from Chicago to Caribbean in December is currently the most expensive (average of $195). 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$450FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$119Average$445FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$130Average$343FlexibilityNo cancel feeOn-time65%
DeltaCheapest$136Average$549FlexibilityNo cancel feeOn-timeN/A
ArajetCheapest$185Average$320FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$193Average$576FlexibilityNo cancel feeOn-time67%
Hahn AirCheapest$213Average$343FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$603FlexibilityNo cancel feeOn-time69%

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