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Cheap flights from Hamilton, Ontario to Chicago from C$ 230

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hamilton, Ontario to Chicago departing on 12/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Hamilton, Ontario to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
2:35 p.m. - 5:32 a.m.YHM-ORD
15h 57m2 stops
Multiple Airlines Logo
2:20 p.m. - 11:47 p.m.ORD-YHM
32h 27m1 stop
C$ 608Multiple Airlines
Find Deal
Fri, 28 Nov - Fri, 5 Dec
Multiple Airlines Logo
6:10 p.m. - 1:35 p.m.YHM-ORD
20h 25m1 stop
Multiple Airlines Logo
9:06 p.m. - 7:00 p.m.ORD-YHM
44h 54m2 stops
C$ 705Multiple Airlines
Find Deal
Sun, 30 Nov - Sun, 7 Dec
Multiple Airlines Logo
8:15 a.m. - 5:32 a.m.YHM-ORD
22h 17m2 stops
Multiple Airlines Logo
9:06 p.m. - 11:47 p.m.ORD-YHM
25h 41m2 stops
C$ 718Multiple Airlines
Find Deal
Fri, 28 Nov - Fri, 5 Dec
Multiple Airlines Logo
8:15 a.m. - 5:32 a.m.YHM-ORD
22h 17m2 stops
Multiple Airlines Logo
2:20 p.m. - 7:00 p.m.ORD-YHM
27h 40m3 stops
C$ 727Multiple Airlines
Find Deal
Fri, 28 Nov - Fri, 5 Dec
Multiple Airlines Logo
7:00 a.m. - 9:17 a.m.YHM-ORD
27h 17m3 stops
Multiple Airlines Logo
2:20 p.m. - 7:00 p.m.ORD-YHM
27h 40m3 stops
C$ 736Multiple Airlines
Find Deal
Fri, 28 Nov - Fri, 5 Dec
Multiple Airlines Logo
7:55 p.m. - 11:14 a.m.YHM-ORD
16h 19m2 stops
Multiple Airlines Logo
2:20 p.m. - 11:55 p.m.ORD-YHM
32h 35m1 stop
C$ 791Multiple Airlines
Find Deal
Mon, 27 Oct - Thu, 30 Oct
Multiple Airlines Logo
6:10 p.m. - 5:32 a.m.YHM-ORD
36h 22m3 stops
Multiple Airlines Logo
9:06 p.m. - 11:47 p.m.ORD-YHM
25h 41m2 stops
C$ 864Multiple Airlines
Find Deal
Sun, 30 Nov - Sun, 7 Dec
Multiple Airlines Logo
8:15 a.m. - 1:35 p.m.YHM-ORD
30h 20m2 stops
Multiple Airlines Logo
9:06 p.m. - 11:47 p.m.ORD-YHM
25h 41m2 stops
C$ 908Multiple Airlines
Find Deal
Sun, 30 Nov - Sun, 7 Dec
Multiple Airlines Logo
7:25 a.m. - 9:00 p.m.YHM-ORD
14h 35m1 stop
Multiple Airlines Logo
5:05 a.m. - 3:00 p.m.ORD-YHM
8h 55m1 stop
C$ 931Multiple Airlines
Find Deal
Thu, 12 Feb - Thu, 19 Feb
Multiple Airlines Logo
6:10 p.m. - 5:32 a.m.YHM-ORD
36h 22m3 stops
Multiple Airlines Logo
7:15 a.m. - 7:00 p.m.ORD-YHM
34h 45m3 stops
C$ 979Multiple Airlines
Find Deal
Sun, 30 Nov - Sun, 7 Dec

momondo Fare Finder

 
Customize your flight search to find flights from Hamilton, Ontario 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 96,600 searches. Data last updated 16 October 2025.
Use the filters below to find and compare flights from Hamilton, Ontario to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 28/11

2:35 p.m.-5:32 a.m.

2 stops15h 57m

Chicago O'Hare Intl

Fri 5/12

2:20 p.m.-11:47 p.m.

1 stop32h 27m

C$ 608

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 30/11

6:10 p.m.-1:35 p.m.

1 stop20h 25m

Chicago O'Hare Intl

Sun 7/12

9:06 p.m.-7:00 p.m.

2 stops44h 54m

C$ 705

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 28/11

8:15 a.m.-5:32 a.m.

2 stops22h 17m

Chicago O'Hare Intl

Fri 5/12

9:06 p.m.-11:47 p.m.

2 stops25h 41m

C$ 718

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 28/11

8:15 a.m.-5:32 a.m.

2 stops22h 17m

Chicago O'Hare Intl

Fri 5/12

2:20 p.m.-7:00 p.m.

3 stops27h 40m

C$ 727

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 28/11

7:00 a.m.-9:17 a.m.

3 stops27h 17m

Chicago O'Hare Intl

Fri 5/12

2:20 p.m.-7:00 p.m.

3 stops27h 40m

C$ 736

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Mon 27/10

7:55 p.m.-11:14 a.m.

2 stops16h 19m

Chicago O'Hare Intl

Thu 30/10

2:20 p.m.-11:55 p.m.

1 stop32h 35m

C$ 791

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 30/11

6:10 p.m.-5:32 a.m.

3 stops36h 22m

Chicago O'Hare Intl

Sun 7/12

9:06 p.m.-11:47 p.m.

2 stops25h 41m

C$ 864

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 30/11

8:15 a.m.-1:35 p.m.

2 stops30h 20m

Chicago O'Hare Intl

Sun 7/12

9:06 p.m.-11:47 p.m.

2 stops25h 41m

C$ 908

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 12/2

7:25 a.m.-9:00 p.m.

1 stop14h 35m

Chicago O'Hare Intl

Thu 19/2

5:05 a.m.-3:00 p.m.

1 stop8h 55m

C$ 931

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 30/11

6:10 p.m.-5:32 a.m.

3 stops36h 22m

Chicago O'Hare Intl

Sun 7/12

7:15 a.m.-7:00 p.m.

3 stops34h 45m

C$ 979

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 Chicago from

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

The month of June is another great option to travel to Chicago, with average flight prices from Hamilton, Ontario averaging around C$ 313.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 638. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,113. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the evening is the cheapest time of day to fly from Hamilton, Ontario to Chicago when you can find flight prices for as low as C$ 639. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,089 per ticket.

When to book flights from Hamilton, Ontario to Chicago

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

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

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

Direct flights

None
There are no direct flights from Hamilton, Ontario to Chicago. There are no popular flight routes from Hamilton, Ontario to Chicago.
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  • How far is Hamilton to Chicago by plane?

    There are 654.3 km between Hamilton and Chicago. Typically, this will take 12h 14m by plane in normal conditions.

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

    Prices for flights from Hamilton Airport to Chicago refresh daily.

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

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

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

    The necessary travel and health documents for your Chicago 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.

  • What is the most popular airline from Hamilton, Ontario to Chicago?

Best airlines flying from Hamilton, Ontario to Chicago

Compare and see reviews for airlines that fly from Hamilton, Ontario to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 309Free CancellationRating
7.1
10,306 reviews
Search Air Canada flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

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

It is quick and easy to find Hamilton 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 Hamilton to Chicago with flexible booking policies on momondo?

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

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

momondo helps you find the best flight between Hamilton 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 Hamilton to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Hamilton to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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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 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport