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Cheap flights from Chicago to Toronto from $129

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Toronto departing on 9/25. 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

Find the cheapest flights from Chicago to Toronto

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
5:30 pm - 5:15 pmORD  Chicago O'Hare Intl-YHM Hamilton
22h 45m1 stop Calgary
WestJet Logo
6:10 pm - 4:40 pmYHM  Hamilton-ORD Chicago O'Hare Intl
23h 30m1 stop Calgary
$516WestJet
Thu, Oct 1 - Sun, Oct 4
WestJet Logo
5:30 pm - 5:15 pmORD  Chicago O'Hare Intl-YHM Hamilton
22h 45m1 stop Calgary
WestJet Logo
6:10 pm - 4:40 pmYHM  Hamilton-ORD Chicago O'Hare Intl
23h 30m1 stop Calgary
$546WestJet
Thu, Sep 10 - Mon, Sep 14
WestJet Logo
5:30 pm - 5:15 pmORD  Chicago O'Hare Intl-YHM Hamilton
22h 45m1 stop Calgary
WestJet Logo
6:10 pm - 4:40 pmYHM  Hamilton-ORD Chicago O'Hare Intl
23h 30m1 stop Calgary
$552WestJet
Thu, Sep 10 - Mon, Sep 14
Multiple Airlines Logo
8:45 am - 7:39 pmORD  Chicago O'Hare Intl-YHM Hamilton
9h 54m2 stops Montreal Pierre Elliott Trudeau Intl Halifax Intl
Multiple Airlines Logo
1:55 pm - 10:15 amYHM  Hamilton-ORD Chicago O'Hare Intl
21h 20m2 stops Halifax Intl Montreal Pierre Elliott Trudeau Intl
$559Multiple Airlines
Thu, Sep 17 - Thu, Sep 24
Multiple Airlines Logo
5:30 pm - 3:05 pmORD  Chicago O'Hare Intl-YHM Hamilton
20h 35m2 stops Calgary Ottawa
Multiple Airlines Logo
6:55 pm - 10:15 amYHM  Hamilton-ORD Chicago O'Hare Intl
16h 20m2 stops Calgary Montreal Pierre Elliott Trudeau Intl
$564Multiple Airlines
Thu, Sep 10 - Thu, Sep 17
Multiple Airlines Logo
3:40 pm - 3:05 pmORD  Chicago O'Hare Intl-YHM Hamilton
22h 25m3 stops Montreal Pierre Elliott Trudeau Intl Calgary Ottawa
Multiple Airlines Logo
11:45 am - 10:15 amYHM  Hamilton-ORD Chicago O'Hare Intl
23h 30m3 stops Ottawa Calgary Montreal Pierre Elliott Trudeau Intl
$568Multiple Airlines
Tue, Sep 15 - Tue, Sep 22
Multiple Airlines Logo
5:30 pm - 3:05 pmORD  Chicago O'Hare Intl-YHM Hamilton
20h 35m2 stops Calgary Ottawa
Multiple Airlines Logo
6:55 pm - 10:15 amYHM  Hamilton-ORD Chicago O'Hare Intl
16h 20m2 stops Calgary Montreal Pierre Elliott Trudeau Intl
$568Multiple Airlines
Thu, Sep 10 - Thu, Sep 17
Multiple Airlines Logo
3:40 pm - 3:05 pmORD  Chicago O'Hare Intl-YHM Hamilton
22h 25m3 stops Montreal Pierre Elliott Trudeau Intl Calgary Ottawa
Multiple Airlines Logo
6:55 pm - 2:52 pmYHM  Hamilton-ORD Chicago O'Hare Intl
20h 57m2 stops Calgary Montreal Pierre Elliott Trudeau Intl
$570Multiple Airlines
Tue, Sep 15 - Tue, Sep 22
Multiple Airlines Logo
5:30 pm - 10:09 pmORD  Chicago O'Hare Intl-YHM Hamilton
27h 39m2 stops Calgary Winnipeg
Multiple Airlines Logo
7:00 am - 4:40 pmYHM  Hamilton-ORD Chicago O'Hare Intl
34h 40m2 stops Winnipeg Calgary
$574Multiple Airlines
Sun, Sep 13 - Sat, Sep 19
Multiple Airlines Logo
7:17 pm - 3:55 pmORD  Chicago O'Hare Intl-YHM Hamilton
19h 38m2 stops Tweed-New Haven Fort Lauderdale
Multiple Airlines Logo
5:45 pm - 10:15 amYHM  Hamilton-ORD Chicago O'Hare Intl
17h 30m2 stops Halifax Intl Montreal Pierre Elliott Trudeau Intl
$574Multiple Airlines
Fri, Sep 18 - Fri, Sep 25

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WestJet flights from Chicago to Hamilton, Ontario

Our best WestJet deals on Chicago to Hamilton, Ontario flight tickets
WestJet
Oct 1
ORD5:30 pmChicago O'Hare Intl
22h 45m
1 stop
YHM5:15 pmHamilton
Oct 4
YHM6:10 pmHamilton
23h 30m
1 stop
ORD4:40 pmChicago O'Hare Intl
$516
WestJet
Sep 10
ORD5:30 pmChicago O'Hare Intl
22h 45m
1 stop
YHM5:15 pmHamilton
Sep 14
YHM6:10 pmHamilton
23h 30m
1 stop
ORD4:40 pmChicago O'Hare Intl
$546
WestJet
Sep 10
ORD5:30 pmChicago O'Hare Intl
22h 45m
1 stop
YHM5:15 pmHamilton
Sep 14
YHM6:10 pmHamilton
23h 30m
1 stop
ORD4:40 pmChicago O'Hare Intl
$552

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Hamilton, Ontario 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 6, 2026.
Use the filters below to find and compare flights from Chicago to Hamilton, Ontario that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoHamilton

ORD Chicago O'Hare Intl - YHM Hamilton

ORDYHM

Chicago O'Hare Intl

Thu 10/1

5:30 pm-5:15 pm

1 stop22h 45m

Hamilton

Sun 10/4

6:10 pm-4:40 pm

1 stop23h 30m

$516

ChicagoHamilton

ORD Chicago O'Hare Intl - YHM Hamilton

ORDYHM

Chicago O'Hare Intl

Thu 9/10

5:30 pm-5:15 pm

1 stop22h 45m

Hamilton

Mon 9/14

6:10 pm-4:40 pm

1 stop23h 30m

$546

ChicagoHamilton

ORD Chicago O'Hare Intl - YHM Hamilton

ORDYHM

Chicago O'Hare Intl

Thu 9/10

5:30 pm-5:15 pm

1 stop22h 45m

Hamilton

Mon 9/14

6:10 pm-4:40 pm

1 stop23h 30m

$552
Quickest round-trip

ChicagoHamilton

ORD Chicago O'Hare Intl - YHM Hamilton

ORDYHM

Chicago O'Hare Intl

Thu 9/17

8:45 am-7:39 pm

2 stops9h 54m

Hamilton

Thu 9/24

1:55 pm-10:15 am

2 stops21h 20m

$559

ChicagoHamilton

ORD Chicago O'Hare Intl - YHM Hamilton

ORDYHM

Chicago O'Hare Intl

Thu 9/10

5:30 pm-3:05 pm

2 stops20h 35m

Hamilton

Thu 9/17

6:55 pm-10:15 am

2 stops16h 20m

$564

ChicagoHamilton

ORD Chicago O'Hare Intl - YHM Hamilton

ORDYHM

Chicago O'Hare Intl

Tue 9/15

3:40 pm-3:05 pm

3 stops22h 25m

Hamilton

Tue 9/22

11:45 am-10:15 am

3 stops23h 30m

$568

ChicagoHamilton

ORD Chicago O'Hare Intl - YHM Hamilton

ORDYHM

Chicago O'Hare Intl

Thu 9/10

5:30 pm-3:05 pm

2 stops20h 35m

Hamilton

Thu 9/17

6:55 pm-10:15 am

2 stops16h 20m

$568

ChicagoHamilton

ORD Chicago O'Hare Intl - YHM Hamilton

ORDYHM

Chicago O'Hare Intl

Tue 9/15

3:40 pm-3:05 pm

3 stops22h 25m

Hamilton

Tue 9/22

6:55 pm-2:52 pm

2 stops20h 57m

$570

ChicagoHamilton

ORD Chicago O'Hare Intl - YHM Hamilton

ORDYHM

Chicago O'Hare Intl

Sun 9/13

5:30 pm-10:09 pm

2 stops27h 39m

Hamilton

Sat 9/19

7:00 am-4:40 pm

2 stops34h 40m

$574

ChicagoHamilton

ORD Chicago O'Hare Intl - YHM Hamilton

ORDYHM

Chicago O'Hare Intl

Fri 9/18

7:17 pm-3:55 pm

2 stops19h 38m

Hamilton

Fri 9/25

5:45 pm-10:15 am

2 stops17h 30m

$574

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Toronto from

How to get the cheapest flight ticket from Chicago to Hamilton, Ontario

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 Chicago to Hamilton?

WestJet is the most popular carrier operating from Chicago to Hamilton

What airlines fly to Hamilton, Ontario?

United Airlines, Air Canada and American Airlines are the top three most popular airlines that fly to Hamilton, Ontario from Chicago according to our data. United Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Hamilton, Ontario. Keep in mind that there are 7 different airlines that fly to Hamilton, Ontario on a routine basis, so you have a few additional options to choose from.

When to book flights from Chicago to Hamilton, Ontario

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Hamilton, Ontario according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Hamilton, Ontario (CHI to YHM) flight deals and tips

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

Fastest flight time

20h 35m

Direct flights

None
The fastest flight from Chicago to Hamilton, Ontario takes 20h 35m
There are no direct flights from Chicago to Hamilton, Ontario. There are no popular flight routes from Chicago to Hamilton, Ontario.
Search flight deals

Frequently asked questions about flying from Chicago to Hamilton, Ontario

  • How far is Chicago to Hamilton by plane?

    Hamilton is 406.6 mi away from Chicago. Flights usually cover this in 20h 35m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Chicago to Hamilton Airport refresh daily.

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Hamilton Airport.

  • What documentation or ID do you need to fly to Hamilton Airport?

    The necessary travel and health documents for your Hamilton Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Hamilton. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. All flights to Hamilton from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once all potential Chicago to Hamilton flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Of course. momondo tracks the price of Chicago to Hamilton 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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