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Cheap flights from Bermuda to Chicago from $274

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Bermuda to Chicago departing on 11/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Bermuda to Chicago

Recent round-trip flight deals from Bermuda to Chicago

Enter your travel dates to find the best prices.
Air Canada Logo
1:35 pm - 2:55 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
27h 20m1 stop Toronto Pearson Intl
Air Canada Logo
3:40 pm - 12:40 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
43h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$531Air Canada
Wed, Sep 23 - Mon, Sep 28
Multiple Airlines Logo
12:50 pm - 7:01 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
8h 11m1 stop Boston Logan Intl
Multiple Airlines Logo
5:35 pm - 12:40 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
17h 05m1 stop Toronto Pearson Intl
$548Multiple Airlines
Sat, Sep 19 - Sat, Sep 26
Multiple Airlines Logo
12:50 pm - 7:01 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
8h 11m1 stop Boston Logan Intl
Multiple Airlines Logo
11:05 am - 12:40 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
23h 35m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$552Multiple Airlines
Sat, Sep 19 - Sat, Sep 26
Air Canada Logo
1:35 pm - 9:00 amBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
21h 25m1 stop Toronto Pearson Intl
Air Canada Logo
11:05 am - 12:40 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
47h 35m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$579Air Canada
Fri, Sep 4 - Mon, Sep 7
Air Canada Logo
1:35 pm - 9:00 amBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
21h 25m1 stop Toronto Pearson Intl
Air Canada Logo
8:45 am - 12:40 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
25h 55m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$579Air Canada
Wed, Sep 2 - Tue, Sep 8
Air Canada Logo
1:35 pm - 1:23 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
25h 48m1 stop Toronto Pearson Intl
Air Canada Logo
3:40 pm - 12:40 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
43h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$579Air Canada
Fri, Sep 18 - Fri, Sep 25
Air Canada Logo
1:35 pm - 10:15 amBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
22h 40m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
3:40 pm - 12:40 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
43h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$582Air Canada
Wed, Sep 23 - Mon, Sep 28
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
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
$593Air Canada
Thu, Dec 24 - Thu, Jan 7
American Airlines Logo
3:54 pm - 9:57 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
8h 03m1 stop Charlotte Douglas
American Airlines Logo
8:37 am - 10:35 pmORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
11h 58m1 stop Miami
$732American Airlines
Fri, Sep 4 - Mon, Sep 7
American Airlines Logo
12:48 pm - 9:30 pmBDA  Hamilton L.F Wade Intl-ORD Chicago O'Hare Intl
10h 42m1 stop Philadelphia
American Airlines Logo
7:30 pm - 11:55 amORD  Chicago O'Hare Intl-BDA Hamilton L.F Wade Intl
14h 25m1 stop Philadelphia
$732American Airlines
Fri, Sep 18 - Fri, Sep 25

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Air Canada flights from Bermuda to Chicago

Our best Air Canada deals on Bermuda to Chicago flight tickets
Air Canada
Sep 23
BDA1:35 pmHamilton L.F Wade Intl
27h 20m
1 stop
ORD2:55 pmChicago O'Hare Intl
Sep 28
ORD3:40 pmChicago O'Hare Intl
43h 00m
2 stops
BDA12:40 pmHamilton L.F Wade Intl
$531
Air Canada
Sep 2
BDA1:35 pmHamilton L.F Wade Intl
21h 25m
1 stop
ORD9:00 amChicago O'Hare Intl
Sep 8
ORD8:45 amChicago O'Hare Intl
25h 55m
2 stops
BDA12:40 pmHamilton L.F Wade Intl
$579
Air Canada
Sep 23
BDA1:35 pmHamilton L.F Wade Intl
22h 40m
2 stops
ORD10:15 amChicago O'Hare Intl
Sep 28
ORD3:40 pmChicago O'Hare Intl
43h 00m
2 stops
BDA12:40 pmHamilton L.F Wade Intl
$582

United Airlines flights from Bermuda to Chicago

Our best United Airlines deals on Bermuda to Chicago flight tickets
United Airlines
Dec 16
BDA2:45 pmHamilton L.F Wade Intl
19h 07m
1 stop
ORD7:52 amChicago O'Hare Intl
Dec 30
ORD7:55 pmChicago O'Hare Intl
15h 40m
1 stop
BDA1:35 pmHamilton L.F Wade Intl
$723
United Airlines
Dec 21
BDA2:45 pmHamilton L.F Wade Intl
8h 07m
1 stop
ORD8:52 pmChicago O'Hare Intl
Jan 4
ORD5:00 amChicago O'Hare Intl
6h 35m
1 stop
BDA1:35 pmHamilton L.F Wade Intl
$732
United Airlines
Dec 23
BDA2:45 pmHamilton L.F Wade Intl
20h 08m
1 stop
ORD8:53 amChicago O'Hare Intl
Jan 7
ORD6:00 amChicago O'Hare Intl
5h 35m
1 stop
BDA1:35 pmHamilton L.F Wade Intl
$760

momondo Fare Finder

 
Customize your flight search to find flights from Bermuda to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 9, 2026.
Use the filters below to find and compare flights from Bermuda to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HamiltonChicago

BDA Hamilton L.F Wade Intl - ORD Chicago O'Hare Intl

BDAORD

Hamilton L.F Wade Intl

Wed 9/23

1:35 pm-2:55 pm

1 stop27h 20m

Chicago O'Hare Intl

Mon 9/28

3:40 pm-12:40 pm

2 stops43h 00m

$531

HamiltonChicago

BDA Hamilton L.F Wade Intl - ORD Chicago O'Hare Intl

BDAORD

Hamilton L.F Wade Intl

Sat 9/19

12:50 pm-7:01 pm

1 stop8h 11m

Chicago O'Hare Intl

Sat 9/26

5:35 pm-12:40 pm

1 stop17h 05m

$548

HamiltonChicago

BDA Hamilton L.F Wade Intl - ORD Chicago O'Hare Intl

BDAORD

Hamilton L.F Wade Intl

Sat 9/19

12:50 pm-7:01 pm

1 stop8h 11m

Chicago O'Hare Intl

Sat 9/26

11:05 am-12:40 pm

2 stops23h 35m

$552

HamiltonChicago

BDA Hamilton L.F Wade Intl - ORD Chicago O'Hare Intl

BDAORD

Hamilton L.F Wade Intl

Fri 9/4

1:35 pm-9:00 am

1 stop21h 25m

Chicago O'Hare Intl

Mon 9/7

11:05 am-12:40 pm

2 stops47h 35m

$579

HamiltonChicago

BDA Hamilton L.F Wade Intl - ORD Chicago O'Hare Intl

BDAORD

Hamilton L.F Wade Intl

Wed 9/2

1:35 pm-9:00 am

1 stop21h 25m

Chicago O'Hare Intl

Tue 9/8

8:45 am-12:40 pm

2 stops25h 55m

$579

HamiltonChicago

BDA Hamilton L.F Wade Intl - ORD Chicago O'Hare Intl

BDAORD

Hamilton L.F Wade Intl

Fri 9/18

1:35 pm-1:23 pm

1 stop25h 48m

Chicago O'Hare Intl

Fri 9/25

3:40 pm-12:40 pm

2 stops43h 00m

$579

HamiltonChicago

BDA Hamilton L.F Wade Intl - ORD Chicago O'Hare Intl

BDAORD

Hamilton L.F Wade Intl

Wed 9/23

1:35 pm-10:15 am

2 stops22h 40m

Chicago O'Hare Intl

Mon 9/28

3:40 pm-12:40 pm

2 stops43h 00m

$582

HamiltonChicago

BDA Hamilton L.F Wade Intl - ORD Chicago O'Hare Intl

BDAORD

Hamilton L.F Wade Intl

Thu 12/24

5:50 pm-3:38 pm

1 stop23h 48m

Chicago O'Hare Intl

Thu 1/7

8:45 am-4:45 pm

1 stop6h 00m

$593
Quickest round-trip

HamiltonChicago

BDA Hamilton L.F Wade Intl - ORD Chicago O'Hare Intl

BDAORD

Hamilton L.F Wade Intl

Fri 9/4

3:54 pm-9:57 pm

1 stop8h 03m

Chicago O'Hare Intl

Mon 9/7

8:37 am-10:35 pm

1 stop11h 58m

$732

HamiltonChicago

BDA Hamilton L.F Wade Intl - ORD Chicago O'Hare Intl

BDAORD

Hamilton L.F Wade Intl

Fri 9/18

12:48 pm-9:30 pm

1 stop10h 42m

Chicago O'Hare Intl

Fri 9/25

7:30 pm-11:55 am

1 stop14h 25m

$732

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Bermuda to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Bermuda to Chicago?

Air Canada is the most popular carrier operating from Bermuda to Chicago

Cheap Bermuda to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Bermuda to Chicago

Fastest flight time

7h 07m

Direct flights

None
The fastest flight from Bermuda to Chicago takes 7h 07m
There are no direct flights from Bermuda to Chicago. There are no popular flight routes from Bermuda to Chicago.
Search flight deals

Frequently asked questions about flying from Bermuda to Chicago

  • When did momondo last update prices for flights from Bermuda to Chicago?

    Prices for flights from Bermuda to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from Bermuda to Chicago?

  • How old do you have to be to fly from Bermuda to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Bermuda to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Bermuda to Chicago

Compare and see reviews for airlines that fly from Bermuda to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $741Free CancellationRating
7.1
11,893 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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

Why use momondo?

Why should I use momondo to find a flight deal from Bermuda to Chicago?

It is quick and easy to find Bermuda to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Bermuda to Chicago with flexible booking policies on momondo?

All flight searches from Bermuda to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Bermuda to Chicago?

momondo helps you find the best flight between Bermuda and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Bermuda to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Bermuda to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport