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$150+ Cheap flights from Chicago (CHI) to Barbados

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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BGI
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheap flight deals from Chicago to Barbados

Cheapest flights from Chicago to Barbados
Explore the most affordable flight options available from Chicago to Barbados. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 8, 2026.

This Booking.com deal was found by Cheapflights users on 1/8. 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 1/173:55 pmORD - BGI
2 stops22h 00mAir Canada
Sun 1/254:55 pmBGI - ORD
1 stop29h 15mAir Canada
Deal found 1/8$374
This Air Canada deal was found by Cheapflights users on 1/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/198:45 pmORD - BGI
1 stop15h 50mAir Canada
Thu 1/224:55 pmBGI - ORD
1 stop24h 00mAir Canada
Deal found 1/7$388
This Air Canada deal was found by Cheapflights users on 1/6. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:40 pmORD - BGI
1 stop22h 15mAir Canada
Sat 10/313:05 pmBGI - ORD
1 stop19h 55mAir Canada
Deal found 1/6$389
This Air Canada deal was found by Cheapflights users on 1/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/201:55 pmORD - BGI
2 stops24h 00mAir Canada
Thu 1/224:55 pmBGI - ORD
1 stop24h 00mAir Canada
Deal found 1/7$393
This Air Canada deal was found by Cheapflights users on 1/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:20 pmORD - BGI
1 stop18h 00mAir Canada
Sat 6/134:20 pmBGI - ORD
1 stop17h 40mAir Canada
Deal found 1/7$394
This Air Canada deal was found by Cheapflights users on 1/6. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/208:45 pmORD - BGI
2 stops17h 10mAir Canada
Fri 1/234:10 pmBGI - ORD
2 stops24h 45mAir Canada
Deal found 1/6$400
This Air Canada deal was found by Cheapflights users on 1/6. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:00 pmORD - BGI
2 stops22h 40mAir Canada
Sat 10/102:40 pmBGI - ORD
2 stops22h 03mAir Canada
Deal found 1/6$404
This Air Canada deal was found by Cheapflights users on 1/8. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/267:25 amORD - BGI
2 stops30h 00mAir Canada
Thu 4/23:55 pmBGI - ORD
2 stops23h 05mAir Canada
Deal found 1/8$405

Find flight deals from Chicago to Barbados

Keep the following information in mind while searching for Chicago to Barbados flight deals. Data was last updated January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$388
(Air Canada)

One-way from

$150
(Air Canada)

Popular in

June

Cheapest in

September

Average price

$681
Provider with most accurate pricing for Chicago (CHI)-Bridgetown Grantley Adams Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Bridgetown Grantley Adams Intl flights.
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From Chicago (CHI) to Barbados
Search Deals
One-way flight from Chicago (CHI) to Barbados
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Barbados 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 8, 2026.
Use the filters below to find and compare flights from Chicago to Barbados that are best for you.

Fly from

Chicago

Fly to

Barbados

Route

Depart

Return

Price

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Tue 1/20

5:52 pm-3:55 pm

1 stop20h 03m

Bridgetown Grantley Adams Intl

Thu 1/22

4:55 pm-6:51 pm

1 stop27h 56m

$393

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Sun 5/31

8:20 pm-3:20 pm

1 stop18h 00m

Bridgetown Grantley Adams Intl

Sat 6/6

4:20 pm-9:00 am

1 stop17h 40m

$394

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Sat 6/6

6:20 pm-3:20 pm

2 stops20h 00m

Bridgetown Grantley Adams Intl

Sat 6/13

4:20 pm-9:00 am

1 stop17h 40m

$399

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Mon 1/19

9:15 pm-3:55 pm

2 stops40h 40m

Bridgetown Grantley Adams Intl

Thu 1/22

4:55 pm-6:55 pm

2 stops28h 00m

$402

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Sat 5/16

8:20 pm-3:20 pm

1 stop18h 00m

Bridgetown Grantley Adams Intl

Sat 5/23

4:20 pm-9:00 am

1 stop17h 40m

$415

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Sat 6/20

8:40 pm-3:25 pm

1 stop17h 45m

Bridgetown Grantley Adams Intl

Sat 6/27

4:20 pm-9:00 am

1 stop17h 40m

$415

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Sat 2/21

7:15 am-3:55 pm

1 stop30h 40m

Bridgetown Grantley Adams Intl

Tue 3/3

4:10 pm-3:10 pm

1 stop25h 00m

$419

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Wed 3/25

2:00 pm-2:55 pm

2 stops23h 55m

Bridgetown Grantley Adams Intl

Wed 4/1

3:35 pm-1:00 pm

2 stops22h 25m

$425

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Sun 2/22

12:50 pm-3:55 pm

1 stop25h 05m

$150

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Sat 2/21

8:40 pm-3:55 pm

2 stops17h 15m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

Showing 1-10 of 20 results
1
2

Best time to book a flight from Chicago to Barbados

Have a flexible travel schedule? Discover the best time to fly to Barbados 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 Barbados

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Barbados (average of $186). Flying from Chicago to Barbados in May is currently the most expensive (average of $630). 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.

Reviews of airlines servicing Barbados

Get insights into the airlines that provide service to Barbados. 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 Barbados. Reviews last updated January 8, 2026.
Peruse reviews from past customers who have flown with Delta, American Airlines, and JetBlue from Chicago to Barbados to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,029 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Comfort

7.9

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
8,029 reviews
Delta
7.9
Good
8,029 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Comfort

7.9

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
11,095 reviews
Delta
7.9
Good
8,029 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Comfort

7.9

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.
JetBlue
7.2
Good
2,893 reviews
Delta
7.9
Good
8,029 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Comfort

7.9

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 Barbados. 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 Barbados?

    There are many flights that can get you from Chicago to Barbados in 20h 03m. Fly via Air Canada to get the fastest option. The distance between Chicago and Barbados is about 2623 mi.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Chicago to Barbados (average of $186). Flying from Chicago to Barbados in May is currently the most expensive (average of $630). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Barbados

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Chicago to Barbados

Discover the top 2 airlines that operate flights from Chicago to Barbados. 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 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$338Average$606FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$495Average$656FlexibilityNo cancel feeOn-time71%

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