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$279+ Cheap flights from Barbados 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
BGI — CHI
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
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Cheap flight deals from Barbados to Chicago

One-way flights from Barbados to Chicago
Search for one-way flight options from Barbados to Chicago. Find affordable one-way fares based on user searches. Data last updated December 21, 2025.

This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/204:10 pmBGI - ORD
1 stop19h 56mAir Canada
Deal found 12/21$279
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/304:00 pmBGI - ORD
1 stop9h 35mUnited Airlines
Deal found 12/21$644
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/42:00 pmBGI - ORD
3 stops53h 00mMultiple Airlines
Deal found 12/21$837
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/48:00 amBGI - ORD
1 stop19h 33mAmerican Airlines
Deal found 12/21$1,454
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.
Tue 12/308:00 amBGI - ORD
2 stops11h 49mAmerican Airlines
Deal found 12/20$1,794
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/304:10 pmBGI - ORD
2 stops33h 34mAir Canada
Deal found 12/21$1,935

Cheapflights Fare Finder

 
Customize your flight search to find flights from Barbados 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 21, 2025.
Use the filters below to find and compare flights from Barbados to Chicago that are best for you.

Fly from

Barbados

Fly to

Chicago

Route

Depart

Return

Price

BridgetownChicago

BGI - ORD

BGIORD

Bridgetown Grantley Adams Intl

Tue 1/20

4:10 pm-10:06 am

1 stop19h 56m

$279

BridgetownChicago

BGI - ORD

BGIORD

Bridgetown Grantley Adams Intl

Tue 12/30

4:00 pm-11:35 pm

1 stop9h 35m

$644

BridgetownChicago

BGI - ORD

BGIORD

Bridgetown Grantley Adams Intl

Sun 1/4

2:00 pm-5:00 pm

3 stops53h 00m

$837

BridgetownChicago

BGI - ORD

BGIORD

Bridgetown Grantley Adams Intl

Tue 12/30

8:00 am-5:49 pm

2 stops11h 49m

$1,794

BridgetownChicago

BGI - ORD

BGIORD

Bridgetown Grantley Adams Intl

Tue 12/30

4:10 pm-11:44 pm

2 stops33h 34m

$1,935

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Best time to book a flight from Barbados to Chicago

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

What is the cheapest time of day to fly from BB to CHI?

Find hourly flight availability from Barbados 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 21, 2025.

A simple way to save on the total cost of your ticket is to fly from Barbados to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 56% on your trip compared to booking a flight in the morning.

Related info for your journey

Find useful and relevant information for your journey from Barbados to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Barbados 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.

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

Browse thousands of different options on Cheapflights for your next trip

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