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Cheap flights from Hamilton, ON to Chicago from C$ 315

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 17/8. Fares are subject to change and may not be available on all flights or dates of travel.
YHM — CHI
23 Aug — 30 Aug1
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
Explore the most affordable flight options available from Hamilton to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 July 2026.

Mon 7/98:15 a.m.
YHM
-
ORD
1 stop29h 35m
Multiple Airlines
Mon 14/95:30 p.m.
ORD
-
YHM
2 stops25h 04m
Multiple Airlines
Deal found 23/7C$ 579
Thu 17/96:10 p.m.
YHM
-
ORD
1 stop23h 30m
WestJet
Sun 20/95:30 p.m.
ORD
-
YHM
1 stop22h 45m
WestJet
Deal found 23/7C$ 688
Fri 4/96:10 p.m.
YHM
-
ORD
1 stop23h 30m
WestJet
Sun 13/95:30 p.m.
ORD
-
YHM
1 stop22h 45m
WestJet
Deal found 22/7C$ 707
Fri 4/96:10 p.m.
YHM
-
ORD
1 stop23h 30m
WestJet
Tue 8/95:30 p.m.
ORD
-
YHM
1 stop22h 45m
WestJet
Deal found 19/7C$ 762
Thu 24/96:05 a.m.
YHM
-
ORD
3 stops35h 35m
Multiple Airlines
Mon 28/95:30 p.m.
ORD
-
YHM
3 stops27h 55m
Multiple Airlines
Deal found 20/7C$ 793
Thu 10/96:10 p.m.
YHM
-
ORD
1 stop23h 30m
WestJet
Sun 13/95:30 p.m.
ORD
-
YHM
1 stop22h 45m
WestJet
Deal found 22/7C$ 891
Fri 4/98:50 a.m.
YHM
-
ORD
2 stops12h 40m
Multiple Airlines
Sun 6/98:05 a.m.
ORD
-
YHM
1 stop30h 50m
Multiple Airlines
Deal found 21/7C$ 902

Find flight deals from Hamilton to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Hamilton (YHM) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 24 July 2026.

Round-trip from

C$ 579

One-way from

C$ 315

Popular in

June

Cheapest in

September

Average price

C$ 390
7/9-14/9
  • 7/9-14/9
  • 3 total stops
  • 54h 39m total
  • Hamilton to Chicago
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17/8
  • 17/8
  • 1 total stop
  • 29h 35m total
  • Hamilton to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease (C$ 4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Hamilton 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, Cheapflights users made 629,999 searches. Data last updated 24 July 2026.
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 - ORD

YHMORD

Hamilton

Mon 7/9

8:15 a.m.-12:50 p.m.

1 stop29h 35m

Chicago O'Hare Intl

Mon 14/9

5:30 p.m.-7:34 p.m.

2 stops25h 04m

C$ 579

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 4/9

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

1 stop23h 30m

Chicago O'Hare Intl

Sun 13/9

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

1 stop22h 45m

C$ 707

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 4/9

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

1 stop23h 30m

Chicago O'Hare Intl

Tue 8/9

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

1 stop22h 45m

C$ 762

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Tue 11/8

6:55 p.m.-7:53 p.m.

2 stops25h 58m

Chicago O'Hare Intl

Mon 24/8

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

1 stop28h 43m

C$ 926

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 3/9

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

1 stop23h 30m

Chicago O'Hare Intl

Sun 6/9

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

1 stop22h 45m

C$ 942
Quickest round-trip

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 13/8

6:10 p.m.-5:24 p.m.

3 stops24h 14m

Chicago O'Hare Intl

Sun 16/8

5:30 p.m.-3:08 p.m.

2 stops20h 38m

C$ 1,109

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 13/8

6:10 p.m.-5:24 p.m.

3 stops24h 14m

Chicago O'Hare Intl

Mon 17/8

5:30 p.m.-3:08 p.m.

2 stops20h 38m

C$ 1,223

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 27/8

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

1 stop23h 30m

Chicago O'Hare Intl

Sat 29/8

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

1 stop22h 45m

C$ 1,244
Cheapest one-way

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 4/10

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

1 stop23h 30m

C$ 390

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 17/9

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

1 stop23h 30m

C$ 403

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/7

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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

Find useful and relevant information for your journey from Hamilton to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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. 1 airline has 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.

  • What is the cheapest airline to fly from Hamilton, Ontario to Chicago round-trip?

    Flying on Air Canada is currently your cheapest option to Chicago, with prices starting at C$ 328.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Hamilton to Chicago

Discover the top airline that operate flights from Hamilton to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 24 July 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 328AverageC$ 483FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Hamilton to Chicago?

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.

Why should you use Cheapflights to find cheap flight tickets from Hamilton to Chicago?

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.

Can Cheapflights find flights from Hamilton to Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Hamilton to Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Hamilton to Chicago become cheaper?

Of course! You can now track prices for flights from Hamilton to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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