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$390+ Cheap flights from Chicago (CHI) to Barbados

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BGI
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
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 December 23, 2025.

This Expedia deal was found by Cheapflights users on 12/21. 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.
Wed 12/246:00 pmORD - BGI
2 stops19h 55mAir Canada
Tue 12/304:10 pmBGI - ORD
2 stops28h 43mAir Canada
Deal found 12/21$513
This FlightHub deal was found by Cheapflights users on 12/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:55 pmORD - BGI
2 stops22h 00mAir Canada
Wed 12/314:55 pmBGI - ORD
2 stops22h 06mAir Canada
Deal found 12/21$523
This Expedia deal was found by Cheapflights users on 12/20. 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 12/2910:00 amORD - BGI
1 stop26h 35mAir Canada
Thu 1/14:55 pmBGI - ORD
2 stops22h 06mAir Canada
Deal found 12/20$575
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:59 pmORD - BGI
1 stop17h 21mDelta
Wed 12/314:30 pmBGI - ORD
1 stop19h 06mDelta
Deal found 12/21$588
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:59 pmORD - BGI
1 stop17h 21mDelta
Tue 12/304:30 pmBGI - ORD
2 stops26h 52mDelta
Deal found 12/21$593
This Priceline deal was found by Cheapflights users on 12/21. 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.
Wed 12/247:41 pmORD - BGI
1 stop16h 14mMultiple Airlines
Fri 12/264:10 pmBGI - ORD
1 stop17h 53mMultiple Airlines
Deal found 12/21$661
This Expedia deal was found by Cheapflights users on 12/21. 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.
Wed 12/248:30 pmORD - BGI
2 stops17h 25mAir Canada
Fri 12/264:10 pmBGI - ORD
2 stops17h 55mAir Canada
Deal found 12/21$669
This American Airlines deal was found by Cheapflights users on 12/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:00 amORD - BGI
1 stop7h 44mAmerican Airlines
Thu 1/18:00 amBGI - ORD
1 stop10h 12mAmerican Airlines
Deal found 12/20$717

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 December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$390
(Mytrip)

Popular in

June

Cheapest in

September

Average price

$636
Provider with most accurate pricing for Chicago (CHI)-Bridgetown Grantley Adams Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Bridgetown Grantley Adams Intl flights.
Search Deals
From Chicago (CHI) to Barbados
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 23, 2025.
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

Mon 1/5

8:45 pm-2:35 pm

1 stop15h 50m

Bridgetown Grantley Adams Intl

Wed 1/14

4:55 pm-2:55 pm

1 stop24h 00m

$390

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Mon 6/1

8:20 pm-3:20 pm

1 stop18h 00m

Bridgetown Grantley Adams Intl

Wed 6/10

4:20 pm-9:00 am

1 stop17h 40m

$412

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Tue 6/2

8:20 pm-3:20 pm

1 stop18h 00m

Bridgetown Grantley Adams Intl

Wed 6/10

4:20 pm-9:00 am

1 stop17h 40m

$412

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

$412

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Wed 1/21

1:55 pm-3:55 pm

2 stops24h 00m

Bridgetown Grantley Adams Intl

Wed 1/28

4:55 pm-2:55 pm

1 stop24h 00m

$430

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Wed 1/7

3:35 pm-3:55 pm

1 stop22h 20m

Bridgetown Grantley Adams Intl

Wed 1/28

4:55 pm-2:55 pm

1 stop24h 00m

$430

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Mon 1/19

8:00 am-2:35 pm

1 stop28h 35m

Bridgetown Grantley Adams Intl

Thu 1/22

4:55 pm-6:55 pm

2 stops28h 00m

$434

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Mon 1/12

3:55 pm-2:35 pm

1 stop20h 40m

Bridgetown Grantley Adams Intl

Sat 1/17

4:55 pm-6:55 pm

2 stops28h 00m

$434

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Mon 1/5

8:45 pm-2:35 pm

1 stop15h 50m

Bridgetown Grantley Adams Intl

Fri 1/9

4:10 pm-5:48 pm

1 stop27h 38m

$438

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

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 $633). 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 BB?

Find hourly flight availability from Chicago to Barbados. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

It’s typically best to fly out from Chicago to Barbados in the afternoon. Doing so could potentially save you 33% on the flight price compared to flying at noon, which is usually more expensive.

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 December 23, 2025.
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
8,014 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.1

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
8,014 reviews
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.1

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
11,050 reviews
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.1

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
2,898 reviews
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.1

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 15h 50m. 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 $633). 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$338Average$651FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$495Average$661FlexibilityNo cancel feeOn-time71%

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