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 60% 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.

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

WestJet is the most popular carrier 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 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 December 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$ 226 Cheap Flights from Hamilton to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Hamilton, Ontario and Chicago?

Prices are currently typical for flights on this route. Typical prices usually range from C$ 317 to C$ 646. The lowest price recently found on this route was C$ 384.

1 adult

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Find the cheapest flights from Hamilton, Ontario to Chicago

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:25 a.m. - 9:03 p.m.

YHM

ORD

14h 38m1 stop

5:15 a.m. - 3:00 p.m.

ORD

YHM

8h 45m1 stop

C$ 384Multiple Airlines

Wed, 28 Jan - Wed, 4 Feb

7:25 a.m. - 11:46 p.m.

YHM

ORD

17h 21m1 stop

5:15 a.m. - 3:00 p.m.

ORD

YHM

8h 45m1 stop

C$ 388Multiple Airlines

Wed, 28 Jan - Wed, 4 Feb

7:25 a.m. - 5:52 p.m.

YHM

ORD

11h 27m2 stops

5:15 a.m. - 3:00 p.m.

ORD

YHM

8h 45m1 stop

C$ 423Multiple Airlines

Wed, 28 Jan - Wed, 4 Feb

7:25 a.m. - 5:52 p.m.

YHM

ORD

11h 27m2 stops

5:15 a.m. - 3:00 p.m.

ORD

YHM

8h 45m1 stop

C$ 427Multiple Airlines

Wed, 28 Jan - Wed, 4 Feb

6:10 p.m. - 4:51 p.m.

YHM

ORD

47h 41m2 stops

5:15 a.m. - 3:00 p.m.

ORD

YHM

8h 45m1 stop

C$ 434Multiple Airlines

Thu, 29 Jan - Thu, 5 Feb

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

YHM

ORD

20h 25m1 stop

5:15 a.m. - 3:00 p.m.

ORD

YHM

8h 45m1 stop

C$ 438Multiple Airlines

Thu, 29 Jan - Thu, 5 Feb

5:45 a.m. - 6:27 p.m.

YHM

ORD

37h 42m2 stops

5:32 p.m. - 3:00 p.m.

ORD

YHM

20h 28m1 stop

C$ 442Multiple Airlines

Tue, 27 Jan - Tue, 3 Feb

7:25 a.m. - 7:38 p.m.

YHM

ORD

13h 13m1 stop

5:15 a.m. - 3:00 p.m.

ORD

YHM

8h 45m1 stop

C$ 498Multiple Airlines

Sun, 25 Jan - Wed, 28 Jan

7:00 a.m. - 11:46 p.m.

YHM

ORD

17h 46m3 stops

5:15 a.m. - 3:00 p.m.

ORD

YHM

8h 45m1 stop

C$ 503Multiple Airlines

Thu, 29 Jan - Thu, 5 Feb

7:00 a.m. - 11:46 p.m.

YHM

ORD

17h 46m3 stops

8:43 p.m. - 2:20 p.m.

ORD

YHM

16h 37m2 stops

C$ 505Multiple Airlines

Thu, 29 Jan - Thu, 5 Feb

WestJet flights from Hamilton, Ontario to Chicago

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

WestJet

11 Jun

YHM6:00 a.m.Hamilton

11h 43m

1 stop

ORD4:43 p.m.Chicago O'Hare Intl

14 Jun

ORD5:30 p.m.Chicago O'Hare Intl

30h 10m

1 stop

YHM12:40 a.m.Hamilton

C$ 929

Find similar

WestJet

11 Jun

YHM6:00 a.m.Hamilton

16h 58m

2 stops

ORD9:58 p.m.Chicago O'Hare Intl

14 Jun

ORD9:30 a.m.Chicago O'Hare Intl

14h 10m

2 stops

YHM12:40 a.m.Hamilton

C$ 2,293

Find similar

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

Wed 28/1

7:25 a.m.-9:03 p.m.

1 stop14h 38m

Chicago O'Hare Intl

Wed 4/2

5:15 a.m.-3:00 p.m.

1 stop8h 45m

C$ 384

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Wed 28/1

7:25 a.m.-11:46 p.m.

1 stop17h 21m

Chicago O'Hare Intl

Wed 4/2

5:15 a.m.-3:00 p.m.

1 stop8h 45m

C$ 388

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Wed 28/1

7:25 a.m.-5:52 p.m.

2 stops11h 27m

Chicago O'Hare Intl

Wed 4/2

5:15 a.m.-3:00 p.m.

1 stop8h 45m

C$ 423

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Wed 28/1

7:25 a.m.-5:52 p.m.

2 stops11h 27m

Chicago O'Hare Intl

Wed 4/2

5:15 a.m.-3:00 p.m.

1 stop8h 45m

C$ 427

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 29/1

6:10 p.m.-4:51 p.m.

2 stops47h 41m

Chicago O'Hare Intl

Thu 5/2

5:15 a.m.-3:00 p.m.

1 stop8h 45m

C$ 434

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 29/1

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

1 stop20h 25m

Chicago O'Hare Intl

Thu 5/2

5:15 a.m.-3:00 p.m.

1 stop8h 45m

C$ 438

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Tue 27/1

5:45 a.m.-6:27 p.m.

2 stops37h 42m

Chicago O'Hare Intl

Tue 3/2

5:32 p.m.-3:00 p.m.

1 stop20h 28m

C$ 442

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 25/1

7:25 a.m.-7:38 p.m.

1 stop13h 13m

Chicago O'Hare Intl

Wed 28/1

5:15 a.m.-3:00 p.m.

1 stop8h 45m

C$ 498

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 29/1

7:00 a.m.-11:46 p.m.

3 stops17h 46m

Chicago O'Hare Intl

Thu 5/2

5:15 a.m.-3:00 p.m.

1 stop8h 45m

C$ 503

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 29/1

7:00 a.m.-11:46 p.m.

3 stops17h 46m

Chicago O'Hare Intl

Thu 5/2

8:43 p.m.-2:20 p.m.

2 stops16h 37m

C$ 505

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 typical price of a round-trip flight between Hamilton, Ontario and Chicago?

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$ 307.

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$ 585. 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$ 1,048. 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$ 627. 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$ 1,081 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

Fastest flight time	10h 48m
Direct flights	None

The fastest flight from Hamilton, Ontario to Chicago takes 10h 48m

There are no direct flights from Hamilton, Ontario to Chicago. There are no popular flight routes from Hamilton, Ontario to Chicago.

Search flight deals

How far is Hamilton to Chicago by plane?
There are 654.3 km between Hamilton and Chicago. Typically, this will take 10h 48m 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 December 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$ 300	Free Cancellation	Rating 7.1 10,525 reviews		Search Air Canada flights

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.