$524 Find Cheap Flights from Chicago to Bermuda

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Bermuda departing on 10/12. 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

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Cheap Flights from Chicago to Bermuda

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Hamilton
Hamilton1 stop$524
Hamilton
Hamilton1 stop$524

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

Sun, Oct 12 - Sat, Oct 18
Air Canada Logo
6:01 pm - 11:50 amORD-BDA
15h 49m1 stop
Air Canada Logo
5:45 pm - 9:51 amBDA-ORD
18h 06m1 stop
$524Air Canada
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Sat, Oct 4 - Sun, Oct 12
Air Canada Logo
8:40 am - 4:55 pmORD-BDA
6h 15m1 stop
Air Canada Logo
12:50 pm - 7:29 pmBDA-ORD
8h 39m1 stop
$528Air Canada
Find Deal
Tue, Sep 23 - Fri, Sep 26
Air Canada Logo
3:35 pm - 11:50 amORD-BDA
18h 15m2 stops
Air Canada Logo
12:50 pm - 9:51 amBDA-ORD
23h 01m2 stops
$546Air Canada
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Fri, Oct 31 - Mon, Nov 3
JetBlue Logo
6:55 pm - 12:46 pmORD-BDA
15h 51m1 stop
JetBlue Logo
1:51 pm - 10:35 amBDA-ORD
22h 44m1 stop
$616JetBlue
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Thu, Sep 25 - Sun, Sep 28
 Logo
6:10 am - 11:50 amORD-BDA
27h 40m2 stops
 Logo
12:50 pm - 9:58 pmBDA-ORD
35h 08m3 stops
Wed, Sep 24 - Wed, Oct 1
 Logo
6:30 am - 10:25 pmORD-BDA
13h 55m1 stop
 Logo
12:50 pm - 5:33 pmBDA-ORD
6h 43m1 stop
Thu, Oct 30 - Mon, Nov 3
United Airlines Logo
6:02 am - 1:35 pmORD-BDA
5h 33m1 stop
United Airlines Logo
2:45 pm - 8:07 pmBDA-ORD
7h 22m1 stop
$628United Airlines
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Fri, Oct 17 - Tue, Oct 21
American Airlines Logo
9:12 pm - 1:47 pmORD-BDA
14h 35m1 stop
American Airlines Logo
9:00 am - 10:31 pmBDA-ORD
15h 31m1 stop
$653American Airlines
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Fri, Oct 17 - Tue, Oct 21
American Airlines Logo
9:45 am - 9:45 pmORD-BDA
10h 00m2 stops
American Airlines Logo
2:34 pm - 11:50 pmBDA-ORD
11h 16m2 stops
$658American Airlines
Find Deal
Mon, Sep 22 - Fri, Sep 26
United Airlines Logo
6:00 am - 1:40 pmORD-BDA
5h 40m1 stop
United Airlines Logo
2:50 pm - 9:26 pmBDA-ORD
8h 36m1 stop
$718United Airlines
Find Deal
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 $584 (return) on average. On the other hand, the most expensive months are August and December, when the average cost of round-trip tickets is $1,048 and $842 respectively.

What’s the cheapest day of the week to fly from Chicago to Bermuda?

The average price of all round-trip flights from Chicago to Bermuda clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Bermuda on a Sunday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Chicago to Bermuda. For your return ticket, we recommend flying on a Tuesday and avoiding Fridays for the best deals.

Good to know

Low seasonJuly
Cheapest flight$524
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 17% increase in price.
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.

  • What is the cheapest time of day to fly to Bermuda?

    The cheapest time of day to fly to Bermuda is generally at night, when round-trip flights cost $442 on average. The most expensive time of day to fly to Bermuda is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $607.

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 8944 reviews
7.3Comfort
6.6Food
8.1Crew
7.1Entertainment
7.7Boarding
Airline reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

10.0 ExcellentAnonymous, Aug 2025ORD - MEM
Read more United Airlines reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

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.

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