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Cheap flights from Hamilton, ON to Chicago from C$ 284

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 20/7. Fares are subject to change and may not be available on all flights or dates of travel.
YHM — CHI
12 Jul — 19 Jul1
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 12 June 2026.

Thu 1/106:15 a.m.
YHM
-
ORD
3 stops35h 25m
Multiple Airlines
Sun 4/105:30 p.m.
ORD
-
YHM
3 stops22h 55m
Multiple Airlines
Deal found 8/6C$ 707
Mon 7/98:15 a.m.
YHM
-
ORD
1 stop29h 10m
Multiple Airlines
Sat 12/910:40 p.m.
ORD
-
YHM
2 stops23h 33m
Multiple Airlines
Deal found 12/6C$ 746
Mon 24/88:15 a.m.
YHM
-
ORD
1 stop29h 10m
Multiple Airlines
Sat 29/83:43 p.m.
ORD
-
YHM
2 stops24h 32m
Multiple Airlines
Deal found 10/6C$ 851
Tue 14/76:35 p.m.
YHM
-
ORD
3 stops16h 41m
Multiple Airlines
Thu 16/78:45 a.m.
ORD
-
YHM
2 stops9h 54m
Multiple Airlines
Deal found 10/6C$ 911
Fri 4/93:50 p.m.
YHM
-
ORD
3 stops25h 50m
Multiple Airlines
Sun 6/95:30 p.m.
ORD
-
YHM
2 stops20h 38m
Multiple Airlines
Deal found 8/6C$ 958
Wed 15/78:50 a.m.
YHM
-
ORD
2 stops12h 15m
Multiple Airlines
Wed 22/78:45 a.m.
ORD
-
YHM
2 stops9h 54m
Multiple Airlines
Deal found 9/6C$ 964
Mon 13/78:15 a.m.
YHM
-
ORD
2 stops12h 38m
Multiple Airlines
Thu 16/75:30 p.m.
ORD
-
YHM
1 stop28h 43m
Multiple Airlines
Deal found 8/6C$ 979
Tue 30/66:35 p.m.
YHM
-
ORD
3 stops21h 15m
Multiple Airlines
Thu 2/73:40 p.m.
ORD
-
YHM
2 stops20h 19m
Multiple Airlines
Deal found 10/6C$ 988

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 12 June 2026.

Round-trip from

C$ 707

One-way from

C$ 284

Popular in

May

Cheapest in

September

Average price

C$ 391
1/10-4/10
  • 1/10-4/10
  • 6 total stops
  • 58h 20m total
  • Hamilton to Chicago
Search Deals
20/7
  • 20/7
  • 1 total stop
  • 29h 00m total
  • Hamilton to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 32 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 June 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 12 June 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

Thu 1/10

6:15 a.m.-4:40 p.m.

3 stops35h 25m

Chicago O'Hare Intl

Sun 4/10

5:30 p.m.-5:25 p.m.

3 stops22h 55m

C$ 707
Quickest round-trip

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Wed 15/7

8:50 a.m.-8:05 p.m.

2 stops12h 15m

Chicago O'Hare Intl

Wed 22/7

8:45 a.m.-7:39 p.m.

2 stops9h 54m

C$ 964

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 13/8

6:15 a.m.-4:40 p.m.

3 stops35h 25m

Chicago O'Hare Intl

Sun 16/8

5:30 p.m.-10:09 p.m.

2 stops27h 39m

C$ 996

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 4/9

3:50 p.m.-4:40 p.m.

3 stops25h 50m

Chicago O'Hare Intl

Sun 6/9

5:30 p.m.-8:25 p.m.

3 stops25h 55m

C$ 1,123

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 6/9

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

1 stop23h 30m

Chicago O'Hare Intl

Thu 10/9

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

1 stop22h 45m

C$ 1,239

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 25/6

6:35 p.m.-10:16 a.m.

2 stops16h 41m

Chicago O'Hare Intl

Mon 29/6

8:35 a.m.-7:39 p.m.

2 stops10h 04m

C$ 1,271

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Tue 14/7

7:00 a.m.-5:39 p.m.

3 stops35h 39m

Chicago O'Hare Intl

Thu 16/7

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

2 stops20h 38m

C$ 1,289

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 17/7

10:25 a.m.-5:52 a.m.

3 stops20h 27m

Chicago O'Hare Intl

Mon 20/7

5:30 p.m.-5:25 p.m.

3 stops22h 55m

C$ 1,289

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 14/8

6:15 a.m.-4:40 p.m.

3 stops35h 25m

Chicago O'Hare Intl

Mon 17/8

5:30 p.m.-8:25 p.m.

3 stops25h 55m

C$ 1,292

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 27/8

6:55 p.m.-2:55 p.m.

2 stops21h 00m

Chicago O'Hare Intl

Fri 28/8

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

2 stops20h 38m

C$ 1,320

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Showing 1-10 of 22 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
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.

  • 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$ 270.

  • 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 12 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 270AverageC$ 520FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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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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