$181 Find Cheap Flights from Chicago to Bermuda - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Bermuda departing on 8/24. 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

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Book Cheap Chicago to Bermuda Plane Tickets

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

Thu, Oct 1 - Sun, Oct 4
Air Canada Logo
5:35 pm - 12:40 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
17h 05m1 stop Toronto Pearson Intl
Air Canada Logo
1:35 pm - 7:48 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
8h 13m1 stop Toronto Pearson Intl
$402Air Canada
Thu, Oct 1 - Sun, Oct 4
Air Canada Logo
3:40 pm - 12:40 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
19h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
1:35 pm - 7:48 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
8h 13m1 stop Toronto Pearson Intl
$405Air Canada
Sat, Oct 24 - Sun, Nov 1
Air Canada Logo
9:50 am - 3:25 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
27h 35m1 stop Toronto Pearson Intl
Air Canada Logo
4:30 pm - 9:23 amBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
18h 53m1 stop Toronto Pearson Intl
$436Air Canada
Sat, Oct 24 - Sun, Nov 1
Air Canada Logo
9:50 am - 3:25 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
27h 35m1 stop Toronto Pearson Intl
Air Canada Logo
4:30 pm - 6:20 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
27h 50m2 stops Toronto Pearson Intl Ottawa
$436Air Canada
Sat, Oct 24 - Thu, Nov 5
Air Canada Logo
3:45 pm - 3:25 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
21h 40m1 stop Toronto Pearson Intl
Air Canada Logo
5:50 pm - 3:38 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
23h 48m1 stop Toronto Pearson Intl
$436Air Canada
Wed, Oct 28 - Sun, Nov 1
Air Canada Logo
12:50 pm - 4:45 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
25h 55m1 stop Toronto Pearson Intl
Air Canada Logo
4:30 pm - 1:13 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
22h 43m1 stop Toronto Pearson Intl
$465Air Canada
Thu, Oct 29 - Thu, Nov 5
Air Canada Logo
8:45 am - 4:45 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
6h 00m1 stop Toronto Pearson Intl
Air Canada Logo
5:50 pm - 5:43 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
25h 53m1 stop Toronto Pearson Intl
$466Air Canada
Wed, Oct 28 - Thu, Nov 5
Air Canada Logo
9:05 pm - 4:45 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
17h 40m1 stop Toronto Pearson Intl
Air Canada Logo
5:50 pm - 5:43 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
25h 53m1 stop Toronto Pearson Intl
$466Air Canada
Thu, Sep 3 - Thu, Sep 10
American Airlines Logo
7:30 am - 3:04 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
5h 34m1 stop Charlotte Douglas
American Airlines Logo
12:48 pm - 10:35 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
11h 47m1 stop Philadelphia
$732American Airlines
Thu, Oct 15 - Tue, Oct 20
American Airlines Logo
10:01 am - 9:53 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
9h 52m1 stop Miami
American Airlines Logo
3:59 pm - 11:00 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
9h 01m1 stop Charlotte Douglas
$732American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Bermuda flights

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

What is the cheapest month to fly from Chicago to Bermuda?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Bermuda, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Bermuda is February, when tickets cost $619 (return) on average. On the other hand, the most expensive months are June and August, when the average cost of round-trip tickets is $1,110 and $1,048 respectively.

Good to know

Low season

April

Cheapest flight

$181
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Chicago O'Hare Airport to Hamilton

FAQs - booking Bermuda flights

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

    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 from Chicago to Bermuda.

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

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

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

    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 from Chicago to Bermuda 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 from Chicago to Bermuda?

    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 from Chicago to Bermuda up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago to Bermuda

 
Need help choosing which airline to fly with from Chicago to Bermuda? 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.
7.4
United AirlinesOverall score based on 10085 reviews
7.7Boarding
7.1Entertainment
6.7Food
8.1Crew
7.3Comfort
Airline reviews

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

2.0 MediocreRichard, Aug 2026
Read more United Airlines reviews

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

gate crew was courteous and helpful, flight attendant was nice and friendly once we got going. But we pushed off from the gate relatively on time, then sat there like 10 ft away, for an hour, with no announcement or explanation. Taxiing then took forever, and I get that there was runway congestion, but would be helpful to keep us posted on whats going on

The power outlets were not working for my row. Also felt like the seats have gotten smaller. I was in the window seat and felt like suffocated, as the two passengers next to me were tall and wide.

Terrible. The flight I booked had a convenient departure time. Quick layover. And an arrival timed that worked for the people who had to pick me up. Thanks to delays and rebooking I got none of those things

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

Everything you need to know for your flight from Chicago to Bermuda

Cabin class types available on flights to Bermuda

Cabin classes available on flights to Bermuda. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.