$275 Find Cheap Flights from Barbados to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 11/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Barbados to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Barbados to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Barbados to Chicago

Thu, Oct 30 - Thu, Nov 6
American Airlines Logo
7:00 am - 11:58 pmBGI-ORD
17h 58m1 stop
American Airlines Logo
12:02 pm - 10:27 pmORD-BGI
8h 25m1 stop
$513American Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
American Airlines Logo
7:00 am - 9:10 pmBGI-ORD
15h 10m2 stops
American Airlines Logo
12:02 pm - 10:27 pmORD-BGI
8h 25m1 stop
$518American Airlines
Find Deal
Wed, Oct 29 - Wed, Nov 5
Air Canada Logo
4:00 pm - 11:18 amBGI-ORD
20h 18m2 stops
Air Canada Logo
8:15 pm - 2:25 pmORD-BGI
16h 10m1 stop
$532Air Canada
Find Deal
Sun, Mar 1 - Tue, Mar 3
Delta Logo
4:30 pm - 11:54 pmBGI-ORD
9h 24m1 stop
Delta Logo
5:50 am - 3:20 pmORD-BGI
7h 30m1 stop
$553Delta
Find Deal
Thu, Oct 30 - Mon, Nov 3
American Airlines Logo
7:00 am - 11:58 pmBGI-ORD
17h 58m1 stop
American Airlines Logo
8:10 am - 10:27 pmORD-BGI
12h 17m1 stop
$561American Airlines
Find Deal
Thu, Oct 30 - Mon, Nov 3
American Airlines Logo
3:00 pm - 8:53 amBGI-ORD
18h 53m1 stop
American Airlines Logo
6:46 am - 10:27 pmORD-BGI
13h 41m2 stops
$566American Airlines
Find Deal
Sun, Mar 1 - Tue, Mar 3
Air Canada Logo
4:55 pm - 11:18 amBGI-ORD
20h 23m1 stop
Air Canada Logo
3:55 pm - 3:55 pmORD-BGI
22h 00m2 stops
$604Air Canada
Find Deal
Thu, Oct 30 - Thu, Nov 6
American Airlines Logo
7:00 am - 9:10 pmBGI-ORD
15h 10m2 stops
American Airlines Logo
8:50 am - 10:27 pmORD-BGI
11h 37m2 stops
$630American Airlines
Find Deal
Wed, Oct 29 - Wed, Nov 5
Multiple Airlines Logo
4:00 pm - 6:38 pmBGI-ORD
27h 38m3 stops
Multiple Airlines Logo
10:49 am - 2:25 pmORD-BGI
25h 36m2 stops
$748Multiple Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 13
Multiple Airlines Logo
9:15 pm - 11:57 pmBGI-ORD
27h 42m3 stops
Multiple Airlines Logo
7:43 pm - 2:40 pmORD-BGI
41h 57m3 stops
$765Multiple Airlines
Find Deal

Everything you should know

Cheapest round-trip
$513
American Airlines
Thu 10/30Thu 11/6
BGI - ORD • 1 stop
Cheapest one-way
$275
Air Canada
Wed 11/26
BGI - ORD • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

How long is the flight to Chicago O'Hare Intl Airport?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular route to Chicago on KAYAK is from Bridgetown, which takes 9h 24m.

How many direct flights to Chicago O'Hare Intl Airport are there each day?

There are around 1,623 direct flights from within Barbados to Chicago O'Hare Intl Airport every day. Most flights depart in the morning, with 6:00 am the most common departure time and 52% of flights departing in the morning.

Good to know

Cheapest flight$275
Flight from Bridgetown to Chicago

FAQs - booking Chicago flights

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    Chicago O'Hare Intl Airport is 16 miles from the center of Chicago.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Friday where round-trip tickets can be as cheap as $524. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $1,237 on average.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Chicago O'Hare Intl Airport?

    The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the evening, when round-trip flights cost $542 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the morning, which is peak travel time and where the average cost of a ticket is $1,237.

  • How many direct flights to Chicago O'Hare Intl Airport are there each week?

    Each week there are around 11,355 direct flights from within Barbados to Chicago O'Hare Intl Airport. The most common day for departures is Monday, with 15% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airline flying from Barbados to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Barbados to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 10000 reviews
7.2Comfort
6.4Food
8.0Crew
6.9Entertainment
7.5Boarding
Airline reviews

The flight was on time and crew were nice, seats were tight and there was entertainment available

8.0 ExcellentJohn, Sep 2025YUL - ORD
Read more American Airlines reviews

The flight was on time and crew were nice, seats were tight and there was entertainment available

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Lansing

Everything you need to know for your flight to Chicago

Information on the airport you'll fly into in Chicago

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