$322 Find Cheap Flights from Bermuda 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 11/30. 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
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$549
Multiple Airlines
Thu 12/11Thu 12/18
BDA - MDW • 1 stop
Cheapest one-way
$322
Air Canada
Sun 11/30
BDA - ORD • 2 stops
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Bermuda to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Bermuda 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 Bermuda to Chicago

Thu, Dec 11 - Thu, Dec 18
Multiple Airlines Logo
8:00 am - 1:01 pmBDA-MDW
7h 01m1 stop
Multiple Airlines Logo
7:44 am - 2:15 pmMDW-BDA
28h 31m1 stop
$549Multiple Airlines
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Fri, Jan 30 - Tue, Feb 3
Multiple Airlines Logo
9:35 pm - 1:01 pmBDA-ORD
17h 26m1 stop
Multiple Airlines Logo
8:41 am - 2:15 pmORD-BDA
27h 34m2 stops
$557Multiple Airlines
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Thu, Dec 11 - Thu, Dec 18
Multiple Airlines Logo
8:00 am - 9:19 pmBDA-ORD
15h 19m2 stops
Multiple Airlines Logo
12:50 pm - 8:30 pmORD-BDA
29h 40m2 stops
$558Multiple Airlines
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Fri, Jan 30 - Tue, Feb 3
American Airlines Logo
3:55 pm - 11:27 pmBDA-ORD
9h 32m1 stop
American Airlines Logo
5:00 am - 10:24 pmORD-BDA
15h 24m1 stop
$575American Airlines
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Fri, Jan 30 - Tue, Feb 3
American Airlines Logo
3:55 pm - 11:27 pmBDA-ORD
9h 32m1 stop
American Airlines Logo
10:10 am - 10:24 pmORD-BDA
10h 14m2 stops
$579American Airlines
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Thu, Dec 11 - Thu, Dec 18
Multiple Airlines Logo
3:55 pm - 8:42 pmBDA-ORD
30h 47m2 stops
Multiple Airlines Logo
9:31 am - 2:15 pmORD-BDA
26h 44m1 stop
$590Multiple Airlines
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Fri, Jan 30 - Tue, Feb 3
Multiple Airlines Logo
9:35 pm - 2:55 pmBDA-ORD
19h 20m2 stops
Multiple Airlines Logo
6:05 am - 2:15 pmORD-BDA
30h 10m3 stops
$603Multiple Airlines
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Thu, Apr 23 - Mon, Apr 27
Delta Logo
1:20 pm - 9:36 pmBDA-ORD
10h 16m1 stop
Delta Logo
6:00 am - 2:34 pmORD-BDA
6h 34m1 stop
$657Delta
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Thu, Apr 23 - Mon, Apr 27
Delta Logo
1:20 pm - 8:42 amBDA-MDW
21h 22m2 stops
Delta Logo
6:00 am - 2:34 pmMDW-BDA
6h 34m1 stop
$661Delta
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Thu, Dec 11 - Thu, Dec 18
United Airlines Logo
2:45 pm - 8:07 pmBDA-ORD
7h 22m1 stop
United Airlines Logo
6:00 am - 1:35 pmORD-BDA
5h 35m1 stop
$692United Airlines
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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.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport, with an average flight price of $153.

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Good to know

Cheapest flight$322
Flight from Hamilton to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    9 miles away from Chicago’s city center, Chicago Midway Airport is the closest of the 3 major airports in the city. There are 16 miles separating Chicago city center to Chicago O'Hare Airport, and 79 miles to Chicago Greater Rockford.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Tuesday where tickets can be as cheap as $406. On the other hand, the most expensive day to fly is Friday, where prices are $521 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?

    The cheapest time of day to fly to Chicago is generally in the afternoon, when flights cost $546 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $850.

  • How many direct flights to Chicago are there each week?

    Each week there are around 10,664 direct flights from within Bermuda to Chicago. 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.

Reviews of the top airline flying from Bermuda 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 Bermuda 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 11032 reviews
8.0Crew
6.4Food
7.2Comfort
7.5Boarding
6.9Entertainment
Airline reviews

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

8.0 ExcellentKrishna, Oct 2025BOS - ORD
Read more American Airlines reviews

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Premium economy seat was decent. As always poor headphones, poor food and beverage, crew is not overly friendly

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicago
Business Class flights to Chicago
Prem Econ Class flights to Chicago
Economy Class flights to Chicago

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