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

WestJet is the most popular carrier operating from Hamilton to Chicago

Which airlines fly to Chicago?

Air Canada, United Airlines and Porter Airlines are the top three most popular airlines that fly to Chicago from Hamilton, Ontario according to our data. Air Canada is the first choice among our users, with 68% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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?

There is 1 operator available for flights from Hamilton Airport to Chicago as of August 2025.

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.

C$ 231 Cheap Flights from Hamilton to Chicago in 2025

1 adult

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Find the cheapest flights from Hamilton, Ontario to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

6:00 a.m. - 4:43 p.m.YHM-ORD

11h 43m1 stop

5:30 p.m. - 5:59 p.m.ORD-YHM

23h 29m1 stop

C$ 509

Find Deal

Fri, 19 Sep - Fri, 26 Sep

6:00 a.m. - 4:43 p.m.YHM-ORD

11h 43m1 stop

5:30 p.m. - 11:48 p.m.ORD-YHM

29h 18m2 stops

C$ 549

Find Deal

Fri, 19 Sep - Fri, 26 Sep

2:55 p.m. - 4:43 p.m.YHM-ORD

26h 48m2 stops

5:30 p.m. - 11:48 p.m.ORD-YHM

29h 18m2 stops

C$ 612

Find Deal

Thu, 11 Sep - Thu, 18 Sep

6:00 a.m. - 4:43 p.m.YHM-ORD

11h 43m1 stop

5:30 p.m. - 11:48 p.m.ORD-YHM

29h 18m2 stops

C$ 623

Find Deal

Thu, 11 Sep - Thu, 18 Sep

6:00 a.m. - 4:49 a.m.YHM-ORD

23h 49m3 stops

5:30 p.m. - 11:48 p.m.ORD-YHM

29h 18m2 stops

C$ 699

Find Deal

Thu, 11 Sep - Thu, 18 Sep

6:00 a.m. - 9:32 p.m.YHM-ORD

40h 32m3 stops

5:30 p.m. - 11:48 p.m.ORD-YHM

29h 18m2 stops

C$ 711

Find Deal

Fri, 19 Sep - Fri, 26 Sep

6:00 a.m. - 11:11 p.m.YHM-ORD

18h 11m2 stops

1:40 p.m. - 11:48 p.m.ORD-YHM

9h 08m1 stop

C$ 731

Find Deal

Fri, 22 Aug - Wed, 27 Aug

6:00 a.m. - 4:49 a.m.YHM-ORD

23h 49m3 stops

8:56 p.m. - 12:40 a.m.ORD-YHM

26h 44m3 stops

C$ 746

Find Deal

Thu, 11 Sep - Thu, 18 Sep

6:00 a.m. - 4:44 p.m.YHM-ORD

11h 44m1 stop

6:10 a.m. - 12:41 a.m.ORD-YHM

17h 31m2 stops

C$ 2,260WestJet

Find Deal

Sun, 24 Aug - Mon, 25 Aug

6:00 a.m. - 9:35 p.m.YHM-ORD

16h 35m2 stops

6:10 a.m. - 12:41 a.m.ORD-YHM

17h 31m2 stops

C$ 2,307WestJet

Find Deal

Sun, 24 Aug - Mon, 25 Aug

WestJet flights from Hamilton, Ontario to Chicago

Our best WestJet deals on Hamilton, Ontario to Chicago flight tickets

WestJet

24 Aug

YHM6:00 a.m.Hamilton

11h 44m

1 stop

ORD4:44 p.m.Chicago O'Hare Intl

25 Aug

ORD6:10 a.m.Chicago O'Hare Intl

17h 31m

2 stops

YHM12:41 a.m.Hamilton

C$ 2,260

Find similar

WestJet

24 Aug

YHM6:00 a.m.Hamilton

16h 35m

2 stops

ORD9:35 p.m.Chicago O'Hare Intl

25 Aug

ORD6:10 a.m.Chicago O'Hare Intl

17h 31m

2 stops

YHM12:41 a.m.Hamilton

C$ 2,307

Find similar

Fly from

Fly to

Route

Depart

Return

Price

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 19/9

6:00 a.m.-4:43 p.m.

1 stop11h 43m

Chicago O'Hare Intl

Fri 26/9

5:30 p.m.-5:59 p.m.

1 stop23h 29m

C$ 509

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 19/9

6:00 a.m.-4:43 p.m.

1 stop11h 43m

Chicago O'Hare Intl

Fri 26/9

5:30 p.m.-11:48 p.m.

2 stops29h 18m

C$ 549

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 11/9

2:55 p.m.-4:43 p.m.

2 stops26h 48m

Chicago O'Hare Intl

Thu 18/9

5:30 p.m.-11:48 p.m.

2 stops29h 18m

C$ 612

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 11/9

6:00 a.m.-4:43 p.m.

1 stop11h 43m

Chicago O'Hare Intl

Thu 18/9

5:30 p.m.-11:48 p.m.

2 stops29h 18m

C$ 623

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 11/9

6:00 a.m.-4:49 a.m.

3 stops23h 49m

Chicago O'Hare Intl

Thu 18/9

5:30 p.m.-11:48 p.m.

2 stops29h 18m

C$ 699

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 19/9

6:00 a.m.-9:32 p.m.

3 stops40h 32m

Chicago O'Hare Intl

Fri 26/9

5:30 p.m.-11:48 p.m.

2 stops29h 18m

C$ 711

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 22/8

6:00 a.m.-11:11 p.m.

2 stops18h 11m

Chicago O'Hare Intl

Wed 27/8

1:40 p.m.-11:48 p.m.

1 stop9h 08m

C$ 731

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 11/9

6:00 a.m.-4:49 a.m.

3 stops23h 49m

Chicago O'Hare Intl

Thu 18/9

8:56 p.m.-12:40 a.m.

3 stops26h 44m

C$ 746

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 24/8

6:00 a.m.-4:44 p.m.

1 stop11h 44m

Chicago O'Hare Intl

Mon 25/8

6:10 a.m.-12:41 a.m.

2 stops17h 31m

C$ 2,260

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 24/8

6:00 a.m.-9:35 p.m.

2 stops16h 35m

Chicago O'Hare Intl

Mon 25/8

6:10 a.m.-12:41 a.m.

2 stops17h 31m

C$ 2,307

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

What is the cheapest month to fly to Chicago?

The month of April is another great option to travel to Chicago, with average flight prices from Hamilton, Ontario averaging around C$ 335.

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$ 687. 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$ 1,229. 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$ 594. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,426 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

Best price found	C$ 231
Fastest flight time	11h 43m
Direct flights	None
Airports in Chicago	1 airport

The best one-way flight to Chicago from Hamilton, Ontario in the past 72 hours is C$ 231. The best round-trip flight deal from Hamilton, Ontario to Chicago found on momondo in the last 72 hours is C$ 509.

The fastest flight from Hamilton, Ontario to Chicago takes 11h 43m

There are no direct flights from Hamilton, Ontario to Chicago. Popular non-direct route for this connection is Hamilton Airport - Chicago O'Hare Intl Airport.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

How far is Hamilton to Chicago by plane?
There are 654.3 km between Hamilton and Chicago. Typically, this will take 11h 43m 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?
There is 1 operator available for flights from Hamilton Airport to Chicago as of August 2025.
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?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Hamilton, Ontario to Chicago is Air Canada (100% of total bookings).

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 Canada	PriceFrom C$ 305	Free Cancellation	Rating 7.1 9,851 reviews		Search Air Canada flights

Hammond

Munster

Benton Harbor

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.