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$175+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BGI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Chicago to Barbados

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

Round-trip from

$380
(Air Canada)

One-way from

$175
(American Airlines)

Popular in

June

Cheapest in

December

Average price

$656
From Chicago (CHI) to Barbados
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One-way flight from Chicago (CHI) to Barbados
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Highest demand for flights based on searches. 3% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 17, 2025.

This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/48:25 pmORD - BGI
1 stop17h 15mAir Canada
Tue 10/143:40 pmBGI - ORD
2 stops19h 11mAir Canada
Deal found 9/16$380
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.
Thu 10/29:12 pmORD - BGI
1 stop16h 28mAir Canada
Wed 10/83:40 pmBGI - ORD
2 stops28h 01mAir Canada
Deal found 9/16$390
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/248:25 pmORD - BGI
1 stop17h 15mAir Canada
Thu 10/23:40 pmBGI - ORD
2 stops19h 11mAir Canada
Deal found 9/15$392
This Air Canada deal was found by Cheapflights users on 9/17. 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 11/2912:50 pmORD - BGI
1 stop24h 50mAir Canada
Sat 12/64:55 pmBGI - ORD
1 stop20h 23mAir Canada
Deal found 9/17$395
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/118:15 pmORD - BGI
1 stop16h 10mAir Canada
Tue 11/184:00 pmBGI - ORD
2 stops21h 18mAir Canada
Deal found 9/16$396
This Air Canada deal was found by Cheapflights users on 9/17. 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 11/228:15 pmORD - BGI
2 stops17h 25mAir Canada
Thu 11/274:00 pmBGI - ORD
1 stop19h 13mAir Canada
Deal found 9/17$408

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 September 17, 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

Thu 10/2

9:12 pm-2:40 pm

1 stop16h 28m

Bridgetown Grantley Adams Intl

Wed 10/8

3:40 pm-6:41 pm

2 stops28h 01m

$390

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Tue 11/11

6:05 pm-2:25 pm

2 stops18h 20m

Bridgetown Grantley Adams Intl

Tue 11/18

4:00 pm-11:18 am

2 stops21h 18m

$401

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Sat 10/25

6:00 pm-2:25 pm

2 stops43h 25m

Bridgetown Grantley Adams Intl

Thu 10/30

4:00 pm-9:15 am

1 stop18h 15m

$411

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Sat 11/29

8:15 pm-3:40 pm

2 stops17h 25m

Bridgetown Grantley Adams Intl

Sat 12/6

4:55 pm-11:18 am

1 stop20h 23m

$429

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Mon 11/17

8:15 pm-2:25 pm

1 stop16h 10m

Bridgetown Grantley Adams Intl

Fri 11/21

4:00 pm-11:18 am

2 stops21h 18m

$433

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Sat 11/22

8:15 pm-3:40 pm

2 stops17h 25m

Bridgetown Grantley Adams Intl

Thu 11/27

4:00 pm-9:13 am

1 stop19h 13m

$436

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Tue 1/27

3:35 pm-3:55 pm

1 stop22h 20m

Bridgetown Grantley Adams Intl

Tue 2/3

4:00 pm-11:06 am

2 stops21h 06m

$461

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Fri 10/24

7:05 am-10:11 pm

1 stop14h 06m

$175

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Fri 10/24

2:08 pm-2:25 pm

2 stops47h 17m

$182

ChicagoBridgetown

ORD - BGI

ORDBGI

Chicago O'Hare Intl

Sat 1/3

6:00 am-4:20 pm

1 stop8h 20m

$213

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 13 results
1
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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, October is the cheapest month in which you can book a flight from Chicago to Barbados (average of $556). Flying from Chicago to Barbados in December is currently the most expensive (average of $692). 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 September 17, 2025.

When flying from Chicago to Barbados, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 17, 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
8.0
Very good
7,961 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.2
Good
2,914 reviews
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 16h 28m. 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, October is the cheapest month in which you can book a flight from Chicago to Barbados (average of $556). Flying from Chicago to Barbados in December is currently the most expensive (average of $692). 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$404Average$659FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$522Average$678FlexibilityNo cancel feeOn-time71%

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