$329 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 5/30. 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

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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Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Barbados to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Barbados to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
3:30 pm - 11:58 pmBGI-ORD
9h 28m1 stop
Delta Logo
5:30 am - 2:20 pmORD-BGI
7h 50m1 stop
$471Delta
Find Deal
Fri, May 16 - Sun, May 18
American Airlines Logo
7:00 am - 10:48 pmBGI-ORD
16h 48m1 stop
American Airlines Logo
8:10 am - 9:40 pmORD-BGI
12h 30m1 stop
$480American Airlines
Find Deal
Fri, May 16 - Sun, May 18
American Airlines Logo
7:00 am - 7:40 pmBGI-ORD
13h 40m2 stops
American Airlines Logo
6:00 am - 10:35 pmORD-BGI
15h 35m1 stop
$485American Airlines
Find Deal
Tue, May 20 - Sun, Jun 8
American Airlines Logo
7:00 am - 4:05 pmBGI-ORD
10h 05m1 stop
American Airlines Logo
8:50 pm - 2:40 pmORD-BGI
16h 50m1 stop
$517American Airlines
Find Deal
Thu, May 29 - Thu, Jun 5
American Airlines Logo
7:00 am - 9:43 pmBGI-ORD
15h 43m2 stops
American Airlines Logo
10:03 am - 10:35 pmORD-BGI
11h 32m2 stops
$521American Airlines
Find Deal
Thu, May 29 - Thu, Jun 5
American Airlines Logo
7:00 am - 10:41 pmBGI-ORD
16h 41m1 stop
American Airlines Logo
5:00 am - 2:00 pmORD-BGI
8h 00m1 stop
$553American Airlines
Find Deal
Wed, Aug 27 - Sun, Aug 31
Air Canada Logo
3:40 pm - 8:50 amBGI-ORD
18h 10m1 stop
Air Canada Logo
6:19 pm - 2:35 pmORD-BGI
19h 16m2 stops
$590Air Canada
Find Deal
Fri, May 16 - Sun, May 18
Air Canada Logo
3:40 pm - 6:54 pmBGI-ORD
28h 14m2 stops
Air Canada Logo
6:19 pm - 2:35 pmORD-BGI
19h 16m2 stops
$596Air Canada
Find Deal
Fri, May 16 - Sun, May 18
 Logo
6:10 pm - 11:45 pmBGI-ORD
30h 35m2 stops
 Logo
1:56 pm - 2:40 pmORD-BGI
23h 44m2 stops
Wed, Jun 25 - Fri, Jun 27
 Logo
5:35 pm - 11:45 pmBGI-ORD
31h 10m3 stops
 Logo
5:50 pm - 2:40 pmORD-BGI
43h 50m3 stops
Wed, Jun 25 - Fri, Jun 27
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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 27m.

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

There are around 1,280 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 51% of flights departing in the morning.


Good to know

High seasonApril
Cheapest flight$329
Most popular time to fly and prices are also 8% lower on average.
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 8,958 direct flights from within Barbados to Chicago O'Hare Intl Airport. The most common day for departures is Thursday, 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.

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
7.5Boarding
6.9Entertainment
6.5Food
8.0Crew
Airline reviews

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

2.0 MediocreAnonymous, Apr 2025SDF - ORD
Read more American Airlines reviews

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

Everything you need to know for your flight to Chicago

Information on the airport you'll fly into in Chicago

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