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Cheap flights from Hamilton, ON to Chicago from C$ 372

YHM — CHI
10 Oct — 17 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Hamilton to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Hamilton to Chicago

Thu 1/106:05 a.m. -
3 stops35h 35m
Sun 4/105:30 p.m. -
3 stops23h 05m
Deal found 8/9C$ 652
Sat 10/106:55 p.m. -
2 stops16h 17m
Sun 18/107:54 p.m. -
2 stops26h 19m
Deal found 5/9C$ 813
Sun 11/105:45 p.m. -
2 stops23h 55m
Sun 18/108:04 a.m. -
1 stop30h 51m
Deal found 8/9C$ 829
Thu 1/1011:45 a.m. -
3 stops29h 55m
Mon 5/105:30 p.m. -
3 stops27h 55m
Deal found 7/9C$ 833
Sat 26/96:05 a.m. -
3 stops35h 35m
Tue 29/95:30 p.m. -
2 stops24h 59m
Deal found 8/9C$ 836
Fri 16/1011:45 a.m. -
3 stops23h 27m
Mon 19/105:30 p.m. -
2 stops20h 35m
Deal found 5/9C$ 837

Find flight deals from Hamilton to Chicago

Round-trip from

C$ 652

One-way from

C$ 372

Popular in

October

Cheapest in

February

Average price

C$ 364
1/10-4/10
  • 1/10-4/10
  • 6 total stops
  • 58h 40m total
  • Hamilton to Chicago
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30/9-31/12
  • 30/9-31/12
  • 1 total stop
  • 9h 47m total
  • Hamilton to Chicago
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Highest demand for flights based on searches. 1% potential increase in price (C$ 8 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease (C$ 4 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Hamilton 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

Thu 1/10

7:00 a.m.-4:40 p.m.

2 stops34h 40m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 408

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sat 10/10

5:45 p.m.-4:40 p.m.

2 stops23h 55m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 454
Quickest round-trip

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Thu 22/10

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

1 stop23h 30m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 509

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Sun 4/10

5:45 p.m.-4:40 p.m.

3 stops23h 55m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 645

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Wed 23/9

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

1 stop23h 30m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 692

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Thu 1/10

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

1 stop23h 30m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 700

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Mon 28/9

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

1 stop23h 30m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 797

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

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 815

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Fri 16/10

11:45 a.m.-10:12 a.m.

3 stops23h 27m

Chicago O'Hare Intl

Mon 19/10

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

2 stops20h 35m

C$ 837

HamiltonChicago

YHM Hamilton - ORD Chicago O'Hare Intl

YHMORD

Hamilton

Thu 1/10

5:45 p.m.-4:40 p.m.

2 stops23h 55m

Chicago O'Hare Intl

Mon 5/10

5:30 p.m.-10:34 p.m.

2 stops28h 04m

C$ 858

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

Showing 1-10 of 16 resultsSorted by cheapest first
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Best time to book a flight from Hamilton to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Hamilton with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Hamilton to Chicago

No data available for this route at this time. Please check back soon.

Related info for your journey

  • What airport do you fly from for flights from Hamilton to Chicago?

    For a flight from Hamilton to Chicago, you will be flying from Hamilton. Hamilton (YHM) is just 10.9 km from the centre of the city. Hamilton is the only Hamilton airport and it handles 0 outbound flights to Chicago per day. 0 airlines have flights to Chicago from Hamilton on a regular basis.

  • How long is the flight from Hamilton, Ontario to Chicago?

    WestJet can get you from Hamilton, Ontario to Chicago in just under 23h 30m. Your travel time can differ by up to . Airlines will cover a distance of 666 km.

  • Can I find deals for flights from Hamilton to Chicago that include hotel bookings?

    Yes. In addition to deals on Hamilton to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hamilton to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hamilton to Chicago.

  • Can I find deals for business class flights from Hamilton to Chicago?

    Yes. Cheapflights offers flight deals from Hamilton to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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When you search for this flight from Hamilton to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Hamilton to Chicago.

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