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$108+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find 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 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 12/410:42 amSJU - ORD
1 stop9h 54mMultiple Airlines
Sun 12/77:41 pmORD - SJU
1 stop11h 56mMultiple Airlines
Deal found 10/28$193
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.
Thu 12/410:42 amSJU - MDW
1 stop13h 11mFrontier
Mon 12/86:15 amMDW - SJU
1 stop6h 56mFrontier
Deal found 10/28$196
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/63:37 pmSJU - ORD
1 stop10h 50mSpirit Airlines
Mon 11/178:00 amORD - SJU
Nonstop4h 36mSpirit Airlines
Deal found 10/27$203
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/133:37 pmSJU - ORD
1 stop10h 50mSpirit Airlines
Mon 11/178:00 amORD - SJU
Nonstop4h 36mSpirit Airlines
Deal found 10/27$211
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/44:31 pmSJU - MDW
1 stop7h 41mFrontier
Sun 12/72:59 pmMDW - SJU
1 stop16h 38mFrontier
Deal found 10/28$215
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 12/85:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 10/27$217
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 12/227:15 amSJU - ORD
1 stop29h 40mMultiple Airlines
Tue 1/67:30 amORD - SJU
1 stop14h 19mMultiple Airlines
Deal found 10/27$219
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 12/410:42 amSJU - ORD
1 stop9h 54mMultiple Airlines
Mon 12/85:45 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 10/28$220
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 12/244:16 pmSJU - MDW
1 stop7h 56mFrontier
Sat 1/32:24 pmMDW - SJU
1 stop10h 15mFrontier
Deal found 10/28$223
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.
Fri 12/54:52 pmSJU - ORD
Nonstop5h 28mUnited Airlines
Tue 12/91:05 pmORD - SJU
1 stop7h 17mUnited Airlines
Deal found 10/28$223
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.
Wed 12/243:54 amSJU - ORD
1 stop15h 06mMultiple Airlines
Mon 1/56:05 pmORD - SJU
1 stop16h 54mMultiple Airlines
Deal found 10/27$224
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 12/236:00 amSJU - ORD
1 stop11h 42mMultiple Airlines
Thu 1/15:45 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 10/28$225

Cheap flight deals from Caribbean to Chicago

Keep the following information in mind while searching for Caribbean to Chicago flight deals. Data was last updated October 29, 2025.

Round-trip from

$193
(Kiwi.com)

One-way from

$108
(Cheapflightsfares)

Popular in

August

Cheapest in

January

Average price

$339

Good round-trip deal

$195 or less

Good one-way deal

$171 or less
From Caribbean to Chicago (CHI)
Search Deals
One-way flight from Caribbean to Chicago (CHI)
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Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Caribbean to Chicago (CHI).
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Price to beat on a one-way flight from Caribbean to Chicago (CHI).
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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 October 29, 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 - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/4

10:42 am-9:53 pm

1 stop13h 11m

Chicago Midway

Sun 12/7

6:37 pm-9:55 am

1 stop13h 18m

$221

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/5

7:00 am-11:55 am

1 stop6h 55m

Chicago Midway

Mon 12/8

6:00 am-2:14 pm

1 stop6h 14m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/23

6:15 am-12:01 pm

1 stop7h 46m

Chicago Midway

Tue 2/3

12:48 pm-8:57 pm

1 stop6h 09m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 1/23

6:27 pm-11:57 pm

1 stop7h 30m

Chicago O'Hare Intl

Tue 2/3

7:01 am-4:52 pm

1 stop7h 51m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 12/5

6:38 pm-12:01 am

1 stop7h 23m

Chicago O'Hare Intl

Mon 12/8

5:30 am-2:14 pm

1 stop6h 44m

$227

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 2/14

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 2/21

10:27 am-5:12 pm

Nonstop4h 45m

$243

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 4/25

5:47 am-9:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 5/2

11:27 am-5:12 pm

Nonstop4h 45m

$243

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 11/12

6:17 pm-12:37 am

1 stop8h 20m

Chicago O'Hare Intl

Sun 11/16

8:10 am-4:57 pm

1 stop6h 47m

$251

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Fri 1/16

4:15 pm-11:57 pm

1 stop9h 42m

Chicago O'Hare Intl

Mon 1/19

5:33 am-4:10 pm

1 stop8h 37m

$251

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 1/15

1:52 pm-7:35 pm

1 stop7h 43m

Chicago O'Hare Intl

Mon 1/19

5:33 am-4:10 pm

1 stop8h 37m

$251

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 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, December is the cheapest month in which you can book a flight from Caribbean to Chicago (average of $113). Flying from Caribbean to Chicago in June is currently the most expensive (average of $193). 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 October 29, 2025.

It’s optimal to fly from Caribbean to Chicago in the evening. By choosing this option you can save up to 28% 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 1, 2024.

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.

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 October 29, 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
7,994 reviews

Boarding

8.2

Overall

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Overall

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
United Airlines
7.4
Good
9,001 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Overall

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Overall

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Spirit Airlines
6.3
Okay
8,114 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Overall

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Frontier
5.8
Fair
3,124 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Overall

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!

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 10m. Frontier provides one of the quickest options available for as low as $243. Caribbean and Chicago are separated by a distance of 1982 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 United Airlines. According to our data, you can fly for as low as $109. Users have also found prices from $114 and $114 on Delta and Southwest, 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, San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl and Punta Cana - Chicago Midway.

  • 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 (88%), Air Canada (68%) and United Airlines (68%).

  • What are the cheapest flights from Caribbean to Chicago?

    While on average a flight from Caribbean to Chicago is generally $894, our data shows the cheapest flight currently is $109. When looking at the most popular route, (Punta Cana - Chicago O'Hare Intl), you can expect to pay $240 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, December is the cheapest month in which you can book a flight from Caribbean to Chicago (average of $113). Flying from Caribbean to Chicago in June is currently the most expensive (average of $193). 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
Merrillville
Lansing
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.
John F Kennedy Intl to O'Hare Intl flights
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LaGuardia to St. Louis flights
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Orlando to Midway flights

Top 6 airlines flying from Caribbean to Chicago

Discover the top 6 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$137Average$312FlexibilityNo cancel feeOn-time65%
FrontierCheapest$139Average$312FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$579FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$269Average$533FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$334Average$580FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$384Average$523FlexibilityNo cancel feeOn-time63%

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