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$101+ Cheap flights from Caribbean to Chicago (CHI)

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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap flight deals from Caribbean to Chicago

Cheapest flights from Caribbean to Chicago
Explore the most affordable flight options available from Caribbean to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 15, 2025.

This eDestinos deal was found by Cheapflights users on 12/14. 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.
Thu 12/258:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Mon 1/55:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/14$170
This WAYA deal was found by Cheapflights users on 12/13. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/238:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Sun 1/181:13 pmORD - SJU
1 stop10h 07mMultiple Airlines
Deal found 12/13$173
This Priceline deal was found by Cheapflights users on 12/13. 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.
Sun 12/218:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Mon 1/51:44 pmORD - SJU
1 stop9h 22mMultiple Airlines
Deal found 12/13$184
This Frontier deal was found by Cheapflights users on 12/14. 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.
Sun 12/214:21 pmSJU - ORD
1 stop8h 03mFrontier
Thu 1/83:32 pmORD - SJU
1 stop7h 27mFrontier
Deal found 12/14$185
This Super.com deal was found by Cheapflights users on 12/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/218:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Mon 1/55:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/13$187
This Priceline deal was found by Cheapflights users on 12/13. 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.
Thu 12/256:00 amSJU - MDW
1 stop17h 58mFrontier
Mon 1/56:15 amMDW - SJU
1 stop18h 24mFrontier
Deal found 12/13$192
This Frontier deal was found by Cheapflights users on 12/13. 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 12/243:55 amSJU - ORD
1 stop8h 23mFrontier
Mon 1/51:44 pmORD - SJU
1 stop9h 22mFrontier
Deal found 12/13$192
This CheapOair deal was found by Cheapflights users on 12/13. 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 12/224:21 pmSJU - ORD
1 stop8h 03mFrontier
Mon 1/51:44 pmORD - SJU
1 stop9h 22mFrontier
Deal found 12/13$193
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/238:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Thu 1/17:57 pmORD - SJU
1 stop8h 37mMultiple Airlines
Deal found 12/13$196
This eDestinos deal was found by Cheapflights users on 12/13. 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.
Sat 12/208:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Sat 1/35:00 amORD - SJU
1 stop15h 05mSpirit Airlines
Deal found 12/13$197
This eDestinos deal was found by Cheapflights users on 12/12. 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.
Wed 12/248:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Sat 1/35:00 amORD - SJU
1 stop15h 05mSpirit Airlines
Deal found 12/12$200
This Priceline deal was found by Cheapflights users on 12/13. 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.
Sun 12/217:33 pmSJU - MDW
1 stop20h 32mFrontier
Mon 1/56:15 amMDW - SJU
1 stop18h 24mFrontier
Deal found 12/13$217

Find flight deals from Caribbean to Chicago

Keep the following information in mind while searching for Caribbean to Chicago flight deals. Data was last updated December 15, 2025.

Round-trip from

$166
(eDestinos)

One-way from

$101
(eDestinos)

Popular in

December

Cheapest in

February

Average price

$428

Good round-trip deal

$195 or less

Good one-way deal

$159 or less
From Caribbean to Chicago (CHI)
Search Deals
One-way flight from Caribbean to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Caribbean to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Caribbean to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to Chicago 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 December 15, 2025.
Use the filters below to find and compare flights from Caribbean to Chicago that are best for you.

Fly from

Caribbean

Fly to

Chicago

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/5

11:06 am-7:31 pm

1 stop10h 25m

Chicago O'Hare Intl

Sun 2/8

7:45 am-6:02 pm

1 stop8h 17m

$179

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/5

6:00 am-1:56 pm

1 stop9h 56m

Chicago Midway

Mon 3/9

6:00 am-3:06 pm

1 stop8h 06m

$180

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/15

11:55 am-6:25 pm

1 stop8h 30m

Chicago O'Hare Intl

Wed 1/21

7:20 am-3:35 pm

1 stop6h 15m

$180

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/16

6:00 am-6:54 pm

1 stop14h 54m

Chicago Midway

Sun 1/18

8:19 pm-12:42 pm

1 stop14h 23m

$184

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 1/23

1:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Mon 1/26

12:17 pm-6:49 pm

Nonstop4h 32m

$187

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 2/3

11:06 am-7:36 pm

1 stop10h 30m

Chicago O'Hare Intl

Tue 2/10

8:45 am-7:13 pm

1 stop8h 28m

$202

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 12/26

2:21 pm-10:04 pm

1 stop9h 43m

Chicago O'Hare Intl

Tue 12/30

6:45 am-6:49 pm

1 stop10h 04m

$202

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/9

4:39 pm-10:21 pm

1 stop7h 42m

Chicago Midway

Mon 1/12

4:31 pm-2:50 am

1 stop8h 19m

$203

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 12/23

3:55 am-10:18 am

1 stop8h 23m

Chicago O'Hare Intl

Thu 1/1

7:57 pm-6:34 am

1 stop8h 37m

$204

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/19

4:25 pm-2:26 pm

1 stop24h 01m

Chicago Midway

Sun 2/22

6:00 am-3:03 pm

1 stop7h 03m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 60 results
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Best time to book a flight from Caribbean to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Caribbean 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 Caribbean to Chicago

What is the cheapest month to book a flight from Caribbean to Chicago?

Currently, August is the cheapest month in which you can book a flight from Caribbean to Chicago (average of $121). Flying from Caribbean to Chicago in June is currently the most expensive (average of $175). 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 CB to CHI?

Find hourly flight availability from Caribbean to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 15, 2025.

It’s optimal to fly from Caribbean to Chicago in the evening. By choosing this option you can save up to 26% on the cost of your flight, compared to a flight in the afternoon.

What is the cheapest day to fly from Caribbean to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Caribbean to Chicago. Price data was last updated on December 13, 2025.

Travelers seeking maximum savings on their Caribbean to Chicago flight should consider departing on Thursday afternoons when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Caribbean to Chicago

Explore weekly flight availability from Caribbean to Chicago. 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 December 15, 2025.

The most flights from 0CB to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated December 15, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Caribbean to Chicago. 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
8,010 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

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
8,010 reviews
Delta
7.9
Good
8,010 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

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
9,095 reviews
Delta
7.9
Good
8,010 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

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
11,048 reviews
Delta
7.9
Good
8,010 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

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
8,187 reviews
Delta
7.9
Good
8,010 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

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
5.8
Fair
3,082 reviews
Delta
7.9
Good
8,010 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

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 Caribbean to Chicago. 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 Caribbean to Chicago?

    A quick flight from Caribbean to Chicago can take about 5h 15m. JetBlue provides one of the quickest options available for as low as $187. Caribbean and Chicago are separated by a distance of 2073 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $71. Users have also found prices from $91 and $94 on Frontier and Spirit Airlines, respectively.

  • What are the most popular routes from Caribbean to Chicago?

    The most popular flight routes from Caribbean to Chicago are Punta Cana - Chicago O'Hare Intl, Punta Cana - Chicago Midway and San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl.

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

    The top 3 most reliable airlines when flying from Caribbean to Chicago are Spirit Airlines (81%), Air Canada (76%) and United Airlines (76%).

  • What are the cheapest flights from Caribbean to Chicago?

    While on average a flight from Caribbean to Chicago is generally $821, our data shows the cheapest flight currently is $108. When looking at the most popular route, (Punta Cana - Chicago O'Hare Intl), you can expect to pay $233 for that flight.

  • Can I find deals for flights from Caribbean to Chicago that include hotel bookings?

    Yes. In addition to deals on Caribbean to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Chicago.

  • Can I find deals for business class flights from Caribbean to Chicago?

    Yes. Cheapflights offers flight deals from Caribbean to Chicago 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 Caribbean to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Caribbean to Chicago (average of $121). Flying from Caribbean to Chicago in June is currently the most expensive (average of $175). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Caribbean to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Caribbean to Chicago

Discover the top 7 airlines that operate flights from Caribbean to Chicago. 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$120Average$236FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$138Average$329FlexibilityNo cancel feeOn-time65%
FrontierCheapest$138Average$349FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$626FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$259Average$555FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$271Average$505FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$341Average$525FlexibilityNo cancel feeOn-time63%

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