$350 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 9/22. 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

 
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 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

Wed, Oct 15 - Sat, Oct 18
Air Canada Logo
12:50 pm - 2:01 pmBDA-ORD
27h 11m1 stop
Air Canada Logo
8:40 am - 4:55 pmORD-BDA
6h 15m1 stop
$508Air Canada
Find Deal
Wed, Oct 15 - Sat, Oct 18
Air Canada Logo
12:50 pm - 8:01 amBDA-ORD
21h 11m2 stops
Air Canada Logo
3:35 pm - 11:50 amORD-BDA
18h 15m2 stops
$541Air Canada
Find Deal
Mon, Sep 1 - Mon, Sep 8
Air Canada Logo
12:50 pm - 1:14 pmBDA-ORD
26h 24m1 stop
Air Canada Logo
2:08 pm - 11:50 amORD-BDA
43h 42m2 stops
$546Air Canada
Find Deal
Mon, Sep 1 - Sun, Sep 7
Air Canada Logo
12:50 pm - 7:29 pmBDA-ORD
8h 39m1 stop
Air Canada Logo
8:25 pm - 11:50 amORD-BDA
13h 25m1 stop
$556Air Canada
Find Deal
Fri, Oct 3 - Fri, Oct 10
Air Canada Logo
12:50 pm - 1:14 pmBDA-ORD
26h 24m1 stop
Air Canada Logo
6:06 pm - 4:55 pmORD-BDA
20h 49m2 stops
$559Air Canada
Find Deal
Thu, Sep 11 - Wed, Sep 17
American Airlines Logo
2:31 pm - 9:21 pmBDA-ORD
8h 50m1 stop
American Airlines Logo
5:00 am - 2:10 pmORD-BDA
7h 10m1 stop
$701American Airlines
Find Deal
Thu, Sep 11 - Wed, Sep 17
American Airlines Logo
2:31 pm - 11:52 pmBDA-ORD
11h 21m2 stops
American Airlines Logo
5:00 am - 2:10 pmORD-BDA
7h 10m1 stop
$706American Airlines
Find Deal
Mon, Sep 8 - Fri, Sep 12
 Logo
9:20 am - 10:18 amBDA-ORD
26h 58m3 stops
 Logo
8:25 pm - 4:55 pmORD-BDA
18h 30m2 stops
Thu, Oct 30 - Sun, Nov 2
American Airlines Logo
12:00 pm - 5:26 pmBDA-ORD
7h 26m1 stop
American Airlines Logo
4:06 pm - 11:05 amORD-BDA
16h 59m1 stop
$710American Airlines
Find Deal
Mon, Sep 1 - Mon, Sep 8
American Airlines Logo
9:00 am - 9:25 pmBDA-ORD
14h 25m1 stop
American Airlines Logo
8:47 pm - 2:10 pmORD-BDA
15h 23m1 stop
$816American Airlines
Find Deal
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 (RFD), with an average flight price of $91.

Good to know

Cheapest flight$350
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 round-trip tickets can be as cheap as $406. On the other hand, the most expensive day to fly is Friday, where round-trip 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 round-trip 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 11,485 direct flights from within Bermuda to Chicago. The most common day for departures is Sunday, 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 10000 reviews
7.2Comfort
6.9Entertainment
8.0Crew
6.5Food
7.5Boarding
Airline reviews

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.

6.0 GoodMitchell, Aug 2025CMH - ORD
Read more American Airlines reviews

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..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Traveling to a place near Chicago?

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

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