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 46% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 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 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

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 $230 to $469. The lowest price recently found on this route was $279.

1 adult

0 bags

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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 am - 9:03 pm

YHM

ORD

14h 38m1 stop

5:15 am - 3:00 pm

ORD

YHM

8h 45m1 stop

$279Multiple Airlines

Wed, Jan 28 - Wed, Feb 4

7:25 am - 11:46 pm

YHM

ORD

17h 21m1 stop

5:15 am - 3:00 pm

ORD

YHM

8h 45m1 stop

$282Multiple Airlines

Wed, Jan 28 - Wed, Feb 4

7:25 am - 5:52 pm

YHM

ORD

11h 27m2 stops

5:15 am - 3:00 pm

ORD

YHM

8h 45m1 stop

$307Multiple Airlines

Wed, Jan 28 - Wed, Feb 4

7:25 am - 5:52 pm

YHM

ORD

11h 27m2 stops

5:15 am - 3:00 pm

ORD

YHM

8h 45m1 stop

$310Multiple Airlines

Wed, Jan 28 - Wed, Feb 4

6:10 pm - 4:51 pm

YHM

ORD

47h 41m2 stops

5:15 am - 3:00 pm

ORD

YHM

8h 45m1 stop

$315Multiple Airlines

Thu, Jan 29 - Thu, Feb 5

6:10 pm - 1:35 pm

YHM

ORD

20h 25m1 stop

5:15 am - 3:00 pm

ORD

YHM

8h 45m1 stop

$318Multiple Airlines

Thu, Jan 29 - Thu, Feb 5

5:45 am - 6:27 pm

YHM

ORD

37h 42m2 stops

5:32 pm - 3:00 pm

ORD

YHM

20h 28m1 stop

$321Multiple Airlines

Tue, Jan 27 - Tue, Feb 3

7:25 am - 7:38 pm

YHM

ORD

13h 13m1 stop

5:15 am - 3:00 pm

ORD

YHM

8h 45m1 stop

$362Multiple Airlines

Sun, Jan 25 - Wed, Jan 28

7:00 am - 11:46 pm

YHM

ORD

17h 46m3 stops

5:15 am - 3:00 pm

ORD

YHM

8h 45m1 stop

$365Multiple Airlines

Thu, Jan 29 - Thu, Feb 5

7:00 am - 11:46 pm

YHM

ORD

17h 46m3 stops

8:43 pm - 2:20 pm

ORD

YHM

16h 37m2 stops

$367Multiple Airlines

Thu, Jan 29 - Thu, Feb 5

WestJet flights from Hamilton, Ontario to Chicago

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

WestJet

Jun 11

YHM6:00 amHamilton

11h 43m

1 stop

ORD4:43 pmChicago O'Hare Intl

Jun 14

ORD5:30 pmChicago O'Hare Intl

30h 10m

1 stop

YHM12:40 amHamilton

$675

Find similar

WestJet

Jun 11

YHM6:00 amHamilton

16h 58m

2 stops

ORD9:58 pmChicago O'Hare Intl

Jun 14

ORD9:30 amChicago O'Hare Intl

14h 10m

2 stops

YHM12:40 amHamilton

$1,665

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 1/28

7:25 am-9:03 pm

1 stop14h 38m

Chicago O'Hare Intl

Wed 2/4

5:15 am-3:00 pm

1 stop8h 45m

$279

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Wed 1/28

7:25 am-11:46 pm

1 stop17h 21m

Chicago O'Hare Intl

Wed 2/4

5:15 am-3:00 pm

1 stop8h 45m

$282

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Wed 1/28

7:25 am-5:52 pm

2 stops11h 27m

Chicago O'Hare Intl

Wed 2/4

5:15 am-3:00 pm

1 stop8h 45m

$307

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Wed 1/28

7:25 am-5:52 pm

2 stops11h 27m

Chicago O'Hare Intl

Wed 2/4

5:15 am-3:00 pm

1 stop8h 45m

$310

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 1/29

6:10 pm-4:51 pm

2 stops47h 41m

Chicago O'Hare Intl

Thu 2/5

5:15 am-3:00 pm

1 stop8h 45m

$315

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 1/29

6:10 pm-1:35 pm

1 stop20h 25m

Chicago O'Hare Intl

Thu 2/5

5:15 am-3:00 pm

1 stop8h 45m

$318

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Tue 1/27

5:45 am-6:27 pm

2 stops37h 42m

Chicago O'Hare Intl

Tue 2/3

5:32 pm-3:00 pm

1 stop20h 28m

$321

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 1/25

7:25 am-7:38 pm

1 stop13h 13m

Chicago O'Hare Intl

Wed 1/28

5:15 am-3:00 pm

1 stop8h 45m

$362

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 1/29

7:00 am-11:46 pm

3 stops17h 46m

Chicago O'Hare Intl

Thu 2/5

5:15 am-3:00 pm

1 stop8h 45m

$365

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 1/29

7:00 am-11:46 pm

3 stops17h 46m

Chicago O'Hare Intl

Thu 2/5

8:43 pm-2:20 pm

2 stops16h 37m

$367

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 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 $409. 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 $702.

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 evening. Flights from Hamilton, Ontario to Chicago during this time can be as low as $392. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $581.

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?
Chicago is 406.6 mi away from Hamilton. A reasonable flight in good conditions will take 10h 48m.
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

Valparaiso

Schererville

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.