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

WestJet is the most popular carrier operating from Hamilton to Chicago

What 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 49% 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.

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.

$232 Cheap Flights from Hamilton, Ontario to Chicago in 2026/27

Find the cheapest flights from Hamilton, Ontario to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:15 am - 3:30 pmYHM Hamilton-ORD Chicago O'Hare Intl

8h 15m1 stop Fort Lauderdale

5:30 pm - 3:05 pmORD Chicago O'Hare Intl-YHM Hamilton

20h 35m2 stops Calgary Ottawa

$519Multiple Airlines

Sat, Oct 10 - Fri, Oct 16

6:25 am - 12:50 pmYHM Hamilton-ORD Chicago O'Hare Intl

31h 25m1 stop Fort Lauderdale

5:00 am - 2:53 pmORD Chicago O'Hare Intl-YHM Hamilton

8h 53m1 stop Fort Lauderdale

$523Multiple Airlines

Thu, Dec 17 - Mon, Dec 21

6:25 am - 3:37 pmYHM Hamilton-ORD Chicago O'Hare Intl

10h 12m1 stop Fort Lauderdale

6:10 am - 12:53 amORD Chicago O'Hare Intl-YHM Hamilton

17h 43m1 stop Cancun

$536Multiple Airlines

Sun, Nov 1 - Sun, Nov 8

6:25 am - 9:17 amYHM Hamilton-ORD Chicago O'Hare Intl

27h 52m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson

6:10 am - 12:53 amORD Chicago O'Hare Intl-YHM Hamilton

17h 43m1 stop Cancun

$548Multiple Airlines

Sun, Nov 1 - Sun, Nov 8

6:55 pm - 4:40 pmYHM Hamilton-ORD Chicago O'Hare Intl

22h 45m1 stop Calgary

7:44 pm - 3:55 pmORD Chicago O'Hare Intl-YHM Hamilton

43h 11m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale

$555Multiple Airlines

Wed, Oct 14 - Wed, Oct 21

6:25 am - 7:10 pmYHM Hamilton-ORD Chicago O'Hare Intl

13h 45m2 stops Fort Lauderdale Minneapolis St Paul

5:00 am - 2:53 pmORD Chicago O'Hare Intl-YHM Hamilton

8h 53m1 stop Fort Lauderdale

$580Multiple Airlines

Thu, Dec 17 - Mon, Dec 21

6:25 am - 9:17 amYHM Hamilton-ORD Chicago O'Hare Intl

27h 52m3 stops Fort Lauderdale Dallas/Fort Worth Atlanta Hartsfield-Jackson

6:10 am - 12:53 amORD Chicago O'Hare Intl-YHM Hamilton

17h 43m1 stop Cancun

$594Multiple Airlines

Sun, Nov 1 - Sun, Nov 8

11:45 am - 10:12 amYHM Hamilton-ORD Chicago O'Hare Intl

23h 27m3 stops Ottawa Calgary Montreal Pierre Elliott Trudeau Intl

5:30 pm - 3:05 pmORD Chicago O'Hare Intl-YHM Hamilton

20h 35m2 stops Calgary Ottawa

$604Multiple Airlines

Sat, Oct 10 - Sun, Oct 11

6:55 pm - 10:12 amYHM Hamilton-ORD Chicago O'Hare Intl

16h 17m2 stops Calgary Montreal Pierre Elliott Trudeau Intl

5:30 pm - 3:05 pmORD Chicago O'Hare Intl-YHM Hamilton

20h 35m2 stops Calgary Ottawa

$607Multiple Airlines

Sat, Oct 10 - Sun, Oct 11

6:05 am - 4:40 pmYHM Hamilton-ORD Chicago O'Hare Intl

35h 35m3 stops Montreal St Hubert Winnipeg Calgary

12:37 pm - 5:15 pmORD Chicago O'Hare Intl-YHM Hamilton

27h 38m3 stops Dallas/Fort Worth San Francisco Calgary

$610Multiple Airlines

Wed, Oct 14 - Wed, Oct 21

Cheap last minute flights

Enter your travel dates to find the best prices.

6:05 am - 4:40 pmYHM Hamilton-ORD Chicago O'Hare Intl

35h 35m3 stops Montreal St Hubert Winnipeg Calgary

5:30 pm - 5:35 pmORD Chicago O'Hare Intl-YHM Hamilton

23h 05m3 stops Calgary Winnipeg Montreal St Hubert

$1,049Multiple Airlines

Mon, Sep 21 - Sun, Sep 27

7:00 am - 4:40 pmYHM Hamilton-ORD Chicago O'Hare Intl

34h 40m2 stops Winnipeg Calgary

5:30 pm - 5:35 pmORD Chicago O'Hare Intl-YHM Hamilton

23h 05m3 stops Calgary Winnipeg Montreal St Hubert

$1,054Multiple Airlines

Mon, Sep 21 - Sun, Sep 27

7:00 am - 4:35 pmYHM Hamilton-ORD Chicago O'Hare Intl

10h 35m1 stop Winnipeg

5:30 pm - 5:35 pmORD Chicago O'Hare Intl-YHM Hamilton

23h 05m3 stops Calgary Winnipeg Montreal St Hubert

$1,063Multiple Airlines

Thu, Sep 24 - Sun, Sep 27

7:00 am - 4:35 pmYHM Hamilton-ORD Chicago O'Hare Intl

10h 35m1 stop Winnipeg

5:30 pm - 10:09 pmORD Chicago O'Hare Intl-YHM Hamilton

27h 39m2 stops Calgary Winnipeg

$1,087Multiple Airlines

Thu, Sep 24 - Sun, Sep 27

11:45 am - 4:40 pmYHM Hamilton-ORD Chicago O'Hare Intl

29h 55m3 stops Ottawa Edmonton Calgary

5:30 pm - 3:05 pmORD Chicago O'Hare Intl-YHM Hamilton

20h 35m3 stops Calgary Edmonton Ottawa

$1,287Multiple Airlines

Thu, Sep 24 - Mon, Sep 28

11:45 am - 4:40 pmYHM Hamilton-ORD Chicago O'Hare Intl

29h 55m3 stops Ottawa Edmonton Calgary

5:30 pm - 3:05 pmORD Chicago O'Hare Intl-YHM Hamilton

20h 35m3 stops Calgary Edmonton Ottawa

$1,288Multiple Airlines

Thu, Sep 24 - Mon, Sep 28

5:45 pm - 4:40 pmYHM Hamilton-ORD Chicago O'Hare Intl

23h 55m2 stops Edmonton Calgary

5:30 pm - 3:05 pmORD Chicago O'Hare Intl-YHM Hamilton

20h 35m3 stops Calgary Edmonton Ottawa

$1,329Multiple Airlines

Thu, Sep 24 - Mon, Sep 28

5:45 pm - 4:40 pmYHM Hamilton-ORD Chicago O'Hare Intl

23h 55m2 stops Edmonton Calgary

5:30 pm - 10:25 pmORD Chicago O'Hare Intl-YHM Hamilton

27h 55m3 stops Calgary Edmonton Montreal St Hubert

$1,380Multiple Airlines

Sat, Sep 19 - Fri, Sep 25

5:45 pm - 4:40 pmYHM Hamilton-ORD Chicago O'Hare Intl

23h 55m2 stops Edmonton Calgary

7:17 pm - 3:55 pmORD Chicago O'Hare Intl-YHM Hamilton

19h 38m2 stops Tweed-New Haven Fort Lauderdale

$1,417Multiple Airlines

Sat, Sep 19 - Fri, Sep 25

11:45 am - 7:19 pmYHM Hamilton-ORD Chicago O'Hare Intl

8h 34m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl

8:13 am - 7:39 pmORD Chicago O'Hare Intl-YHM Hamilton

10h 26m2 stops Montreal Pierre Elliott Trudeau Intl Halifax Intl

$1,877Porter Airlines

Sun, Sep 20 - Wed, Sep 23

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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

Cheapest round-trip

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sat 10/10

8:15 am-3:30 pm

1 stop8h 15m

Chicago O'Hare Intl

Fri 10/16

5:30 pm-3:05 pm

2 stops20h 35m

$519

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Thu 12/17

6:25 am-12:50 pm

1 stop31h 25m

Chicago O'Hare Intl

Mon 12/21

5:00 am-2:53 pm

1 stop8h 53m

$523

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sun 11/1

6:25 am-3:37 pm

1 stop10h 12m

Chicago O'Hare Intl

Sun 11/8

6:10 am-12:53 am

1 stop17h 43m

$536

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sun 11/1

6:25 am-9:17 am

2 stops27h 52m

Chicago O'Hare Intl

Sun 11/8

6:10 am-12:53 am

1 stop17h 43m

$548

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Wed 10/14

6:55 pm-4:40 pm

1 stop22h 45m

Chicago O'Hare Intl

Wed 10/21

7:44 pm-3:55 pm

2 stops43h 11m

$555

Quickest round-trip

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Thu 12/17

6:25 am-7:10 pm

2 stops13h 45m

Chicago O'Hare Intl

Mon 12/21

5:00 am-2:53 pm

1 stop8h 53m

$580

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sun 11/1

6:25 am-9:17 am

3 stops27h 52m

Chicago O'Hare Intl

Sun 11/8

6:10 am-12:53 am

1 stop17h 43m

$594

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sat 10/10

11:45 am-10:12 am

3 stops23h 27m

Chicago O'Hare Intl

Sun 10/11

5:30 pm-3:05 pm

2 stops20h 35m

$604

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sat 10/10

6:55 pm-10:12 am

2 stops16h 17m

Chicago O'Hare Intl

Sun 10/11

5:30 pm-3:05 pm

2 stops20h 35m

$607

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Wed 10/14

6:05 am-4:40 pm

3 stops35h 35m

Chicago O'Hare Intl

Wed 10/21

12:37 pm-5:15 pm

3 stops27h 38m

$610

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 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 $454. 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 $660.

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 $403. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $786.

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	$232
Fastest flight time	8h 15m
Direct flights	None

The best one-way flight to Chicago from Hamilton, Ontario in the past 72 hours is $232. The best round-trip flight deal from Hamilton, Ontario to Chicago found on momondo in the last 72 hours is $519.

The fastest flight from Hamilton, Ontario to Chicago takes 8h 15m

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

Search flight deals

Frequently asked questions about flying from Hamilton, Ontario to Chicago

How far is Hamilton to Chicago by plane?
Chicago is 406.6 mi away from Hamilton. A reasonable flight in good conditions will take 8h 15m.
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

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Porter

Crown Point

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.

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Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Hamilton, Ontario to Chicago from $232

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 10/17. 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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Use the filters below to find and compare flights from Hamilton, Ontario to Chicago that are best for you.

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

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

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

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

What airlines fly to Chicago?

When to book flights from Hamilton, Ontario to Chicago

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

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Hamilton, Ontario to Chicago

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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