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Cheap flights from Hamilton, Ontario to Chicago from C$ 273

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 5/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Hamilton, Ontario to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
6:10 p.m. - 4:40 p.m.YHM  Hamilton-ORD Chicago O'Hare Intl
23h 30m1 stop Calgary
WestJet Logo
5:30 p.m. - 5:15 p.m.ORD  Chicago O'Hare Intl-YHM Hamilton
22h 45m1 stop Calgary
C$ 696WestJet
Sun, 4 Oct - Thu, 8 Oct
Multiple Airlines Logo
8:15 a.m. - 9:20 a.m.YHM  Hamilton-ORD Chicago O'Hare Intl
26h 05m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
Multiple Airlines Logo
5:30 p.m. - 5:15 p.m.ORD  Chicago O'Hare Intl-YHM Hamilton
22h 45m1 stop Calgary
C$ 713Multiple Airlines
Sat, 19 Sep - Mon, 21 Sep
Multiple Airlines Logo
6:55 p.m. - 4:40 p.m.YHM  Hamilton-ORD Chicago O'Hare Intl
22h 45m1 stop Calgary
Multiple Airlines Logo
5:30 p.m. - 11:13 p.m.ORD  Chicago O'Hare Intl-YHM Hamilton
28h 43m1 stop Calgary
C$ 769Multiple Airlines
Sat, 19 Sep - Mon, 21 Sep
WestJet Logo
6:10 p.m. - 4:40 p.m.YHM  Hamilton-ORD Chicago O'Hare Intl
23h 30m1 stop Calgary
WestJet Logo
5:30 p.m. - 5:15 p.m.ORD  Chicago O'Hare Intl-YHM Hamilton
22h 45m1 stop Calgary
C$ 771WestJet
Fri, 4 Sep - Mon, 7 Sep
WestJet Logo
6:10 p.m. - 4:40 p.m.YHM  Hamilton-ORD Chicago O'Hare Intl
23h 30m1 stop Calgary
WestJet Logo
5:30 p.m. - 5:15 p.m.ORD  Chicago O'Hare Intl-YHM Hamilton
22h 45m1 stop Calgary
C$ 771WestJet
Sat, 5 Sep - Mon, 7 Sep
WestJet Logo
6:10 p.m. - 4:40 p.m.YHM  Hamilton-ORD Chicago O'Hare Intl
23h 30m1 stop Calgary
WestJet Logo
5:30 p.m. - 5:15 p.m.ORD  Chicago O'Hare Intl-YHM Hamilton
22h 45m1 stop Calgary
C$ 771WestJet
Thu, 3 Sep - Mon, 7 Sep
WestJet Logo
6:10 p.m. - 4:40 p.m.YHM  Hamilton-ORD Chicago O'Hare Intl
23h 30m1 stop Calgary
WestJet Logo
5:30 p.m. - 5:15 p.m.ORD  Chicago O'Hare Intl-YHM Hamilton
22h 45m1 stop Calgary
C$ 771WestJet
Fri, 4 Sep - Mon, 7 Sep
Multiple Airlines Logo
8:35 a.m. - 10:15 a.m.YHM  Hamilton-ORD Chicago O'Hare Intl
26h 40m2 stops Halifax Intl Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
3:40 p.m. - 12:59 p.m.ORD  Chicago O'Hare Intl-YHM Hamilton
20h 19m2 stops Montreal Pierre Elliott Trudeau Intl Halifax Intl
C$ 772Multiple Airlines
Wed, 16 Sep - Wed, 23 Sep
WestJet Logo
6:10 p.m. - 4:40 p.m.YHM  Hamilton-ORD Chicago O'Hare Intl
23h 30m1 stop Calgary
WestJet Logo
5:30 p.m. - 5:15 p.m.ORD  Chicago O'Hare Intl-YHM Hamilton
22h 45m1 stop Calgary
C$ 803WestJet
Sat, 5 Sep - Mon, 7 Sep
WestJet Logo
6:10 p.m. - 4:40 p.m.YHM  Hamilton-ORD Chicago O'Hare Intl
23h 30m1 stop Calgary
WestJet Logo
5:30 p.m. - 5:15 p.m.ORD  Chicago O'Hare Intl-YHM Hamilton
22h 45m1 stop Calgary
C$ 803WestJet
Thu, 3 Sep - Mon, 7 Sep

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WestJet flights from Hamilton, Ontario to Chicago

Our best WestJet deals on Hamilton, Ontario to Chicago flight tickets
WestJet
4 Oct
YHM6:10 p.m.Hamilton
23h 30m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
8 Oct
ORD5:30 p.m.Chicago O'Hare Intl
22h 45m
1 stop
YHM5:15 p.m.Hamilton
C$ 696
WestJet
4 Sep
YHM6:10 p.m.Hamilton
23h 30m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
7 Sep
ORD5:30 p.m.Chicago O'Hare Intl
22h 45m
1 stop
YHM5:15 p.m.Hamilton
C$ 771
WestJet
5 Sep
YHM6:10 p.m.Hamilton
23h 30m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
7 Sep
ORD5:30 p.m.Chicago O'Hare Intl
22h 45m
1 stop
YHM5:15 p.m.Hamilton
C$ 803

momondo Fare Finder

 
Customize your flight search to find flights from Hamilton, Ontario to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 7 August 2026.
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
Quickest round-trip

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sun 4/10

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

1 stop23h 30m

Chicago O'Hare Intl

Thu 8/10

5:30 p.m.-5:15 p.m.

1 stop22h 45m

C$ 696

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sat 19/9

8:15 a.m.-9:20 a.m.

2 stops26h 05m

Chicago O'Hare Intl

Mon 21/9

5:30 p.m.-5:15 p.m.

1 stop22h 45m

C$ 713

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sat 19/9

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

1 stop22h 45m

Chicago O'Hare Intl

Mon 21/9

5:30 p.m.-11:13 p.m.

1 stop28h 43m

C$ 769

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Fri 4/9

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

1 stop23h 30m

Chicago O'Hare Intl

Mon 7/9

5:30 p.m.-5:15 p.m.

1 stop22h 45m

C$ 771

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sat 5/9

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

1 stop23h 30m

Chicago O'Hare Intl

Mon 7/9

5:30 p.m.-5:15 p.m.

1 stop22h 45m

C$ 771

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Thu 3/9

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

1 stop23h 30m

Chicago O'Hare Intl

Mon 7/9

5:30 p.m.-5:15 p.m.

1 stop22h 45m

C$ 771

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Fri 4/9

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

1 stop23h 30m

Chicago O'Hare Intl

Mon 7/9

5:30 p.m.-5:15 p.m.

1 stop22h 45m

C$ 771

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Wed 16/9

8:35 a.m.-10:15 a.m.

2 stops26h 40m

Chicago O'Hare Intl

Wed 23/9

3:40 p.m.-12:59 p.m.

2 stops20h 19m

C$ 772

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sat 5/9

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

1 stop23h 30m

Chicago O'Hare Intl

Mon 7/9

5:30 p.m.-5:15 p.m.

1 stop22h 45m

C$ 803

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Thu 3/9

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

1 stop23h 30m

Chicago O'Hare Intl

Mon 7/9

5:30 p.m.-5:15 p.m.

1 stop22h 45m

C$ 803

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first
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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

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 Tuesday because tickets tend to average around C$ 984. 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 morning is the cheapest time of day to fly from Hamilton, Ontario to Chicago when you can find flight prices for as low as C$ 692. Flying to Chicago in the morning 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$ 1,061 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

16h 20m

Direct flights

None
The fastest flight from Hamilton, Ontario to Chicago takes 16h 20m
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?

    There are 654.3 km between Hamilton and Chicago. Typically, this will take 16h 20m 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?

  • 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.

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 CanadaPriceFrom C$ 327Free CancellationRating
7.1
11,434 reviews
Search Air Canada flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
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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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
Chicago Midway Airport
Chicago O'Hare Intl Airport