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 59% 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 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$ 325 Cheap Flights from Hamilton, Ontario to Chicago in 2026/27

Find the cheapest flights from Hamilton, Ontario to Chicago

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

8:15 a.m. - 3:30 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

8h 15m1 stop Fort Lauderdale

5:30 p.m. - 3:05 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

20h 35m2 stops Calgary Ottawa

C$ 726Multiple Airlines

Sat, 10 Oct - Fri, 16 Oct

6:25 a.m. - 12:50 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

31h 25m1 stop Fort Lauderdale

5:00 a.m. - 2:53 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

8h 53m1 stop Fort Lauderdale

C$ 732Multiple Airlines

Thu, 17 Dec - Mon, 21 Dec

6:25 a.m. - 3:37 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

10h 12m1 stop Fort Lauderdale

6:10 a.m. - 12:53 a.m.ORD Chicago O'Hare Intl-YHM Hamilton

17h 43m1 stop Cancun

C$ 750Multiple Airlines

Sun, 1 Nov - Sun, 8 Nov

8:15 a.m. - 3:30 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

8h 15m1 stop Fort Lauderdale

5:30 p.m. - 3:05 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

20h 35m2 stops Calgary Ottawa

C$ 754Multiple Airlines

Fri, 16 Oct - Mon, 19 Oct

6:25 a.m. - 9:17 a.m.YHM Hamilton-ORD Chicago O'Hare Intl

27h 52m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson

6:10 a.m. - 12:53 a.m.ORD Chicago O'Hare Intl-YHM Hamilton

17h 43m1 stop Cancun

C$ 767Multiple Airlines

Sun, 1 Nov - Sun, 8 Nov

6:55 p.m. - 4:40 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

22h 45m1 stop Calgary

7:44 p.m. - 3:55 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

43h 11m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale

C$ 777Multiple Airlines

Wed, 14 Oct - Wed, 21 Oct

6:25 a.m. - 7:10 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

13h 45m2 stops Fort Lauderdale Minneapolis St Paul

5:00 a.m. - 2:53 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

8h 53m1 stop Fort Lauderdale

C$ 812Multiple Airlines

Thu, 17 Dec - Mon, 21 Dec

6:25 a.m. - 9:17 a.m.YHM Hamilton-ORD Chicago O'Hare Intl

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

6:10 a.m. - 12:53 a.m.ORD Chicago O'Hare Intl-YHM Hamilton

17h 43m1 stop Cancun

C$ 831Multiple Airlines

Sun, 1 Nov - Sun, 8 Nov

6:05 a.m. - 4:40 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

35h 35m3 stops Montreal St Hubert Winnipeg Calgary

12:37 p.m. - 5:15 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

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

C$ 854Multiple Airlines

Wed, 14 Oct - Wed, 21 Oct

6:10 p.m. - 4:40 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

23h 30m1 stop Calgary

7:00 a.m. - 3:55 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

7h 55m1 stop Fort Lauderdale

C$ 866Multiple Airlines

Wed, 14 Oct - Fri, 16 Oct

Cheap last-minute flights

Enter your travel dates to find the best prices.

7:00 a.m. - 4:35 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

10h 35m1 stop Winnipeg

5:30 p.m. - 5:35 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

23h 05m3 stops Calgary Winnipeg Montreal St Hubert

C$ 1,488Multiple Airlines

Thu, 24 Sep - Sun, 27 Sep

7:00 a.m. - 4:35 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

10h 35m1 stop Winnipeg

5:30 p.m. - 10:09 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

27h 39m2 stops Calgary Winnipeg

C$ 1,521Multiple Airlines

Thu, 24 Sep - Sun, 27 Sep

11:45 a.m. - 4:40 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

29h 55m3 stops Ottawa Edmonton Calgary

5:30 p.m. - 3:05 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

20h 35m3 stops Calgary Edmonton Ottawa

C$ 1,801Multiple Airlines

Thu, 24 Sep - Mon, 28 Sep

11:45 a.m. - 4:40 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

29h 55m3 stops Ottawa Edmonton Calgary

5:30 p.m. - 3:05 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

20h 35m3 stops Calgary Edmonton Ottawa

C$ 1,802Multiple Airlines

Thu, 24 Sep - Mon, 28 Sep

5:45 p.m. - 4:40 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

23h 55m2 stops Edmonton Calgary

5:30 p.m. - 3:05 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

20h 35m3 stops Calgary Edmonton Ottawa

C$ 1,860Multiple Airlines

Thu, 24 Sep - Mon, 28 Sep

6:05 a.m. - 2:43 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

33h 38m3 stops Montreal St Hubert Edmonton Vancouver Intl

5:30 p.m. - 3:05 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

20h 35m3 stops Calgary Edmonton Ottawa

C$ 1,977Multiple Airlines

Fri, 25 Sep - Mon, 28 Sep

6:10 p.m. - 9:25 a.m.YHM Hamilton-ORD Chicago O'Hare Intl

16h 15m2 stops Calgary Atlanta Hartsfield-Jackson

5:30 p.m. - 5:15 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

22h 45m1 stop Calgary

C$ 1,986WestJet

Fri, 25 Sep - Sun, 27 Sep

3:45 p.m. - 4:35 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

25h 50m2 stops Montreal St Hubert Winnipeg

5:30 p.m. - 10:25 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

27h 55m3 stops Calgary Winnipeg Montreal St Hubert

C$ 2,231Multiple Airlines

Fri, 25 Sep - Mon, 28 Sep

6:10 p.m. - 12:23 a.m.YHM Hamilton-ORD Chicago O'Hare Intl

31h 13m3 stops Calgary Los Angeles Los Angeles Denver Intl

6:30 a.m. - 5:15 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

33h 45m3 stops Denver Intl Los Angeles Los Angeles Calgary

C$ 2,309Multiple Airlines

Mon, 21 Sep - Wed, 23 Sep

6:05 a.m. - 4:40 p.m.YHM Hamilton-ORD Chicago O'Hare Intl

35h 35m3 stops Montreal St Hubert Edmonton Calgary

5:30 p.m. - 10:25 p.m.ORD Chicago O'Hare Intl-YHM Hamilton

27h 55m3 stops Calgary Edmonton Montreal St Hubert

C$ 2,315Multiple Airlines

Wed, 23 Sep - Fri, 25 Sep

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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 a.m.-3:30 p.m.

1 stop8h 15m

Chicago O'Hare Intl

Fri 16/10

5:30 p.m.-3:05 p.m.

2 stops20h 35m

C$ 726

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Thu 17/12

6:25 a.m.-12:50 p.m.

1 stop31h 25m

Chicago O'Hare Intl

Mon 21/12

5:00 a.m.-2:53 p.m.

1 stop8h 53m

C$ 732

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sun 1/11

6:25 a.m.-3:37 p.m.

1 stop10h 12m

Chicago O'Hare Intl

Sun 8/11

6:10 a.m.-12:53 a.m.

1 stop17h 43m

C$ 750

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Fri 16/10

8:15 a.m.-3:30 p.m.

1 stop8h 15m

Chicago O'Hare Intl

Mon 19/10

5:30 p.m.-3:05 p.m.

2 stops20h 35m

C$ 754

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sun 1/11

6:25 a.m.-9:17 a.m.

2 stops27h 52m

Chicago O'Hare Intl

Sun 8/11

6:10 a.m.-12:53 a.m.

1 stop17h 43m

C$ 767

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Wed 14/10

6:55 p.m.-4:40 p.m.

1 stop22h 45m

Chicago O'Hare Intl

Wed 21/10

7:44 p.m.-3:55 p.m.

2 stops43h 11m

C$ 777

Quickest round-trip

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Thu 17/12

6:25 a.m.-7:10 p.m.

2 stops13h 45m

Chicago O'Hare Intl

Mon 21/12

5:00 a.m.-2:53 p.m.

1 stop8h 53m

C$ 812

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sun 1/11

6:25 a.m.-9:17 a.m.

3 stops27h 52m

Chicago O'Hare Intl

Sun 8/11

6:10 a.m.-12:53 a.m.

1 stop17h 43m

C$ 831

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Wed 14/10

6:05 a.m.-4:40 p.m.

3 stops35h 35m

Chicago O'Hare Intl

Wed 21/10

12:37 p.m.-5:15 p.m.

3 stops27h 38m

C$ 854

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Wed 14/10

6:10 p.m.-4:40 p.m.

1 stop23h 30m

Chicago O'Hare Intl

Fri 16/10

7:00 a.m.-3:55 p.m.

1 stop7h 55m

C$ 866

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 C$ 628. 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 Sunday because tickets tend to average around C$ 937. 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$ 699. 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$ 1,083 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$ 325
Fastest flight time	8h 15m
Direct flights	None

The best one-way flight to Chicago from Hamilton, Ontario in the past 72 hours is C$ 325. The best round-trip flight deal from Hamilton, Ontario to Chicago found on momondo in the last 72 hours is C$ 726.

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.

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Frequently asked questions about flying from Hamilton, Ontario to Chicago

How far is Hamilton to Chicago by plane?
There are 654.3 km between Hamilton and Chicago. Typically, this will take 8h 15m 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 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.

Merrillville

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Hammond

Munster

Valparaiso

Portage

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.

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Cheap flights from Hamilton, Ontario to Chicago from C$ 325

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 17/10. 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.

See travel insights to Chicago from

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?

Which 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

Travelling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

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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 25.6 km from Chicago

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

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