What airlines fly to Chicago?

Air Canada, United Airlines and American 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 51% of people opting to fly with this airline when traveling 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.

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

WestJet and Air Canada are the most popular carriers operating from Hamilton to Chicago

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

Prices for flights from Hamilton Airport to Chicago were last updated today.

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 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.

$164 Cheap Flights from Hamilton to Chicago in 2025/26

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Find the cheapest flights from Hamilton, Ontario to Chicago

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2:35 pm - 5:32 amYHM-ORD

15h 57m2 stops

2:20 pm - 11:47 pmORD-YHM

32h 27m1 stop

$433Multiple Airlines

Find Deal

Fri, Nov 28 - Fri, Dec 5

6:10 pm - 1:35 pmYHM-ORD

20h 25m1 stop

9:06 pm - 7:00 pmORD-YHM

44h 54m2 stops

$502Multiple Airlines

Find Deal

Sun, Nov 30 - Sun, Dec 7

8:15 am - 5:32 amYHM-ORD

22h 17m2 stops

9:06 pm - 11:47 pmORD-YHM

25h 41m2 stops

$511Multiple Airlines

Find Deal

Fri, Nov 28 - Fri, Dec 5

8:15 am - 5:32 amYHM-ORD

22h 17m2 stops

2:20 pm - 7:00 pmORD-YHM

27h 40m3 stops

$518Multiple Airlines

Find Deal

Fri, Nov 28 - Fri, Dec 5

7:00 am - 9:17 amYHM-ORD

27h 17m3 stops

2:20 pm - 7:00 pmORD-YHM

27h 40m3 stops

$524Multiple Airlines

Find Deal

Fri, Nov 28 - Fri, Dec 5

7:55 pm - 11:14 amYHM-ORD

16h 19m2 stops

2:20 pm - 11:55 pmORD-YHM

32h 35m1 stop

$563Multiple Airlines

Find Deal

Mon, Oct 27 - Thu, Oct 30

6:10 pm - 5:32 amYHM-ORD

36h 22m3 stops

9:06 pm - 11:47 pmORD-YHM

25h 41m2 stops

$615Multiple Airlines

Find Deal

Sun, Nov 30 - Sun, Dec 7

8:15 am - 1:35 pmYHM-ORD

30h 20m2 stops

9:06 pm - 11:47 pmORD-YHM

25h 41m2 stops

$647Multiple Airlines

Find Deal

Sun, Nov 30 - Sun, Dec 7

7:25 am - 9:00 pmYHM-ORD

14h 35m1 stop

5:05 am - 3:00 pmORD-YHM

8h 55m1 stop

$663Multiple Airlines

Find Deal

Thu, Feb 12 - Thu, Feb 19

6:10 pm - 5:32 amYHM-ORD

36h 22m3 stops

7:15 am - 7:00 pmORD-YHM

34h 45m3 stops

$697Multiple Airlines

Find Deal

Sun, Nov 30 - Sun, Dec 7

momondo Fare Finder

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 11/28

2:35 pm-5:32 am

2 stops15h 57m

Chicago O'Hare Intl

Fri 12/5

2:20 pm-11:47 pm

1 stop32h 27m

$433

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 11/30

6:10 pm-1:35 pm

1 stop20h 25m

Chicago O'Hare Intl

Sun 12/7

9:06 pm-7:00 pm

2 stops44h 54m

$502

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 11/28

8:15 am-5:32 am

2 stops22h 17m

Chicago O'Hare Intl

Fri 12/5

9:06 pm-11:47 pm

2 stops25h 41m

$511

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 11/28

8:15 am-5:32 am

2 stops22h 17m

Chicago O'Hare Intl

Fri 12/5

2:20 pm-7:00 pm

3 stops27h 40m

$518

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 11/28

7:00 am-9:17 am

3 stops27h 17m

Chicago O'Hare Intl

Fri 12/5

2:20 pm-7:00 pm

3 stops27h 40m

$524

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Mon 10/27

7:55 pm-11:14 am

2 stops16h 19m

Chicago O'Hare Intl

Thu 10/30

2:20 pm-11:55 pm

1 stop32h 35m

$563

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 11/30

6:10 pm-5:32 am

3 stops36h 22m

Chicago O'Hare Intl

Sun 12/7

9:06 pm-11:47 pm

2 stops25h 41m

$615

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 11/30

8:15 am-1:35 pm

2 stops30h 20m

Chicago O'Hare Intl

Sun 12/7

9:06 pm-11:47 pm

2 stops25h 41m

$647

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 2/12

7:25 am-9:00 pm

1 stop14h 35m

Chicago O'Hare Intl

Thu 2/19

5:05 am-3:00 pm

1 stop8h 55m

$663

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 11/30

6:10 pm-5:32 am

3 stops36h 22m

Chicago O'Hare Intl

Sun 12/7

7:15 am-7:00 pm

3 stops34h 45m

$697

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 September is, on average, the cheapest month to fly to Chicago from Hamilton, Ontario, with most prices found around $178. If you’re not able to fly to Chicago in September, then June is your next best option. Flight prices from Hamilton, Ontario to Chicago during June average around $223.

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 $405. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Hamilton, Ontario to Chicago for around $634.

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

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Hamilton, Ontario to Chicago during this time can be as low as $429. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $569.

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?
Chicago is 406.6 mi away from Hamilton. A reasonable flight in good conditions will take 12h 14m.
When did momondo last update prices for flights from Hamilton Airport to Chicago?
Prices for flights from Hamilton Airport to Chicago were last updated today.
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 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.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Hamilton to Chicago for you.

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

Flights from Hamilton to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Hamilton to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

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