$316 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 4/19. 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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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, May 21 - Thu, May 28
Multiple Airlines Logo
8:00 am - 6:38 pm
BDA
-
ORD
12h 38m
1 stop
Multiple Airlines Logo
12:59 pm - 2:20 pm
ORD
-
BDA
23h 21m
1 stop
$547Multiple Airlines
Fri, Jun 5 - Mon, Jun 8
Multiple Airlines Logo
3:30 pm - 10:58 pm
BDA
-
ORD
9h 28m
1 stop
Multiple Airlines Logo
6:22 pm - 12:40 pm
ORD
-
BDA
40h 18m
2 stops
$551Multiple Airlines
Mon, Jun 15 - Fri, Jun 19
JetBlue Logo
3:22 pm - 8:45 am
BDA
-
ORD
19h 23m
1 stop
JetBlue Logo
5:22 pm - 2:17 pm
ORD
-
BDA
18h 55m
1 stop
$559JetBlue
Mon, Jun 15 - Fri, Jun 19
Air Canada Logo
1:35 pm - 7:25 pm
BDA
-
ORD
7h 50m
1 stop
Air Canada Logo
6:22 pm - 12:40 pm
ORD
-
BDA
16h 18m
2 stops
$573Air Canada
Wed, Jun 3 - Sat, Jun 6
Multiple Airlines Logo
3:30 pm - 10:58 pm
BDA
-
ORD
9h 28m
1 stop
Multiple Airlines Logo
3:45 pm - 12:40 pm
ORD
-
BDA
18h 55m
1 stop
$575Multiple Airlines
Wed, Jun 3 - Sat, Jun 6
Multiple Airlines Logo
3:30 pm - 10:58 pm
BDA
-
ORD
9h 28m
1 stop
Multiple Airlines Logo
6:22 pm - 12:40 pm
ORD
-
BDA
16h 18m
2 stops
$580Multiple Airlines
Mon, Jun 15 - Fri, Jun 19
Air Canada Logo
1:35 pm - 7:50 am
BDA
-
ORD
20h 15m
2 stops
Air Canada Logo
6:22 pm - 12:40 pm
ORD
-
BDA
16h 18m
2 stops
$581Air Canada
Fri, Jun 5 - Mon, Jun 8
JetBlue Logo
3:30 pm - 10:58 pm
BDA
-
ORD
9h 28m
1 stop
JetBlue Logo
6:15 am - 2:23 pm
ORD
-
BDA
6h 08m
1 stop
$597JetBlue
Fri, May 1 - Mon, May 4
Delta Logo
1:20 pm - 10:28 pm
BDA
-
MDW
11h 08m
2 stops
Delta Logo
6:00 am - 2:31 pm
MDW
-
BDA
6h 31m
1 stop
$808Delta
Wed, May 6 - Mon, May 18
Delta Logo
3:45 pm - 10:28 pm
BDA
-
MDW
8h 43m
1 stop
Delta Logo
6:23 am - 2:32 pm
MDW
-
BDA
6h 09m
1 stop
$948Delta
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.

What is the cheapest flight to Chicago?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Hamilton, at $547 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $118 in the last 3 days.

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 $160.

Good to know

Cheapest flight$316
Flight from Hamilton to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Hamilton, at $547 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $118 in the last 3 days.

  • 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.

  • 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.

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

    Each week there are around 13,191 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.
7.1
American AirlinesOverall score based on 11563 reviews
6.4Food
7.5Boarding
6.9Entertainment
7.9Crew
7.2Comfort
Airline reviews

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

2.0 MediocreMark, Apr 2026
PHX - ORD
Read more American Airlines reviews

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

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
Griffith
Saint John

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.