HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$108+ Cheap flights from Caribbean Islands 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean Islands to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Caribbean Islands to Chicago

Keep the following information in mind while searching for Caribbean Islands to Chicago flight deals. Data was last updated September 17, 2025.

Round-trip from

$178
(Mytrip)

One-way from

$108
(Mytrip)
From Caribbean Islands to Chicago (CHI)
Search Deals
One-way flight from Caribbean Islands to Chicago (CHI)
Search Deals

Find flight deals from Caribbean Islands to Chicago

Cheapest flights from Caribbean Islands to Chicago
Explore the most affordable flight options available from Caribbean Islands to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Mytrip deal was found by Cheapflights users on 9/15. 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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sat 10/253:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Deal found 9/15$178
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/211:59 amSJU - ORD
1 stop11h 49mSpirit Airlines
Mon 10/69:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/15$186
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 10/279:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/15$192
This Frontier deal was found by Cheapflights users on 9/16. 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 10/269:19 pmSJU - ORD
1 stop10h 51mFrontier
Wed 10/296:40 amORD - SJU
1 stop10h 14mFrontier
Deal found 9/16$197
This Frontier deal was found by Cheapflights users on 9/16. 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.
Sat 10/256:22 amSJU - MDW
2 stops17h 25mFrontier
Fri 10/319:32 amMDW - SJU
1 stop10h 52mFrontier
Deal found 9/16$203
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Fri 10/311:59 amSJU - ORD
1 stop11h 49mSpirit Airlines
Wed 10/86:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Deal found 9/15$206
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/1611:51 amSJU - ORD
1 stop7h 47mSpirit Airlines
Sat 10/183:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Deal found 9/15$208
This Frontier deal was found by Cheapflights users on 9/15. 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.
Fri 10/315:51 pmSJU - ORD
2 stops18h 39mFrontier
Sun 11/25:40 amORD - SJU
1 stop9h 14mFrontier
Deal found 9/15$209
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sat 11/12:03 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Deal found 9/15$214
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 11/132:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Mon 11/176:55 amORD - SJU
Nonstop4h 38mSpirit Airlines
Deal found 9/15$215
This Expedia deal was found by Cheapflights users on 9/16. 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.
Tue 11/257:30 pmPUJ - ORD
Nonstop5h 10mArajet
Tue 12/24:35 amORD - PUJ
Nonstop4h 45mArajet
Deal found 9/16$216
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Wed 10/296:40 amORD - SJU
1 stop10h 14mMultiple Airlines
Deal found 9/15$217

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands 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 September 17, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Chicago that are best for you.

Fly from

Caribbean Islands

Fly to

Chicago

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 10/24

3:56 pm-8:03 pm

Nonstop5h 07m

Chicago O'Hare Intl

Sun 10/26

8:55 am-2:40 pm

Nonstop4h 45m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 11/5

4:52 pm-8:20 pm

Nonstop5h 28m

Chicago O'Hare Intl

Sat 11/8

2:20 pm-9:00 pm

Nonstop4h 40m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/23

3:56 pm-8:03 pm

Nonstop5h 07m

Chicago O'Hare Intl

Sun 10/26

8:55 am-2:40 pm

Nonstop4h 45m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 11/4

8:10 am-11:32 am

Nonstop5h 22m

Chicago O'Hare Intl

Sat 11/8

2:20 pm-9:00 pm

Nonstop4h 40m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 11/12

2:05 am-9:48 am

1 stop9h 43m

Chicago O'Hare Intl

Mon 11/17

2:20 pm-9:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 11/13

6:40 am-11:25 am

1 stop6h 45m

Chicago Midway

Mon 11/17

12:55 pm-11:20 pm

1 stop8h 25m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 10/24

5:43 pm-11:58 pm

1 stop7h 15m

Chicago O'Hare Intl

Mon 10/27

7:00 am-4:25 pm

1 stop8h 25m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 11/5

5:45 am-1:05 pm

2 stops9h 20m

Chicago Midway

Sat 11/8

1:00 pm-12:15 am

1 stop9h 15m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

1:06 pm-9:39 pm

1 stop9h 33m

Chicago O'Hare Intl

Wed 10/29

7:00 am-4:25 pm

1 stop8h 25m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 11/4

5:45 am-2:30 pm

1 stop10h 45m

Chicago Midway

Sat 11/8

1:00 pm-12:15 am

1 stop9h 15m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Caribbean Islands to Chicago

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

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

Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Chicago (average of $245). Flying from Caribbean Islands to Chicago in March is currently the most expensive (average of $321). 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 EPX to CHI?

Find hourly flight availability from Caribbean Islands 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 September 17, 2025.

When flying from Caribbean Islands to Chicago, 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 Caribbean Islands to Chicago

Explore weekly flight availability from Caribbean Islands 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 September 17, 2025.

The most flights from zzEPX to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 September 17, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Caribbean Islands to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,926 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Frontier
5.8
Fair
3,173 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands 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 Islands to Chicago?

    United Airlines, Southwest, and Frontier can get you from Caribbean Islands to Chicago in just under 5h 07m. Your travel time can differ by up to 9h 51m. There are 2073 mi between Caribbean Islands and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

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

    One-way options have recently been found by users for as low as $124 on Frontier. Other airlines that offer cheap prices include Arajet from $134 and United Airlines from $143 one-way.

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

    The most popular route from Caribbean Islands to Chicago is San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl. You may also consider San Juan Luis Munoz Marin Intl - Chicago Midway or Santo Domingo Las Americas - Chicago O'Hare Intl.

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

    The top 3 most reliable airlines when flying from Caribbean Islands to Chicago are Spirit Airlines (82%), Air Canada (81%) and United Airlines (81%).

  • What are the cheapest flights from Caribbean Islands to Chicago?

    While on average a flight from Caribbean Islands to Chicago is generally $515, our data shows the cheapest flight currently is $106. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $177 for that flight.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Chicago (average of $245). Flying from Caribbean Islands to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Caribbean Islands to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Seattle to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Boston to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Denver to O'Hare Intl flights
Ontario to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Santa Ana to O'Hare Intl flights
Baltimore to Midway flights
LaGuardia to Midway flights
Atlanta to Midway flights
Newark to Midway flights
Los Angeles to Midway flights
Dulles Intl to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Austin to O'Hare Intl flights
San Francisco to Midway flights
Raleigh to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Philadelphia to Midway flights
Minneapolis to O'Hare Intl flights
Hobby to Midway flights
Portland to O'Hare Intl flights
Burbank to O'Hare Intl flights
Hobby to O'Hare Intl flights
Mexico City to O'Hare Intl flights
Providence to O'Hare Intl flights
Seattle to Midway flights
Reagan-National to Midway flights
Miami to O'Hare Intl flights
Hartford to O'Hare Intl flights
Denver to Midway flights
Cleveland to O'Hare Intl flights
Love Field to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
San Jose to O'Hare Intl flights
Minneapolis to Midway flights
John F Kennedy Intl to St. Louis flights
San Diego to O'Hare Intl flights

Top 6 airlines flying from Caribbean Islands to Chicago

Discover the top 6 airlines that operate flights from Caribbean Islands 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$136Average$313FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$310FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$448FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$255Average$550FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$502FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$333Average$587FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.