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$128+ Cheap flights from Chicago (CHI) to Hamilton, ON (YHM)

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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YHM
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Chicago to Hamilton

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Hamilton (YHM). 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 September 17, 2025.

Round-trip from

$273
(oojo)

One-way from

$128
(oojo)

Popular in

November

Cheapest in

July

Average price

$258
From Chicago (CHI) to Hamilton
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One-way flight from Chicago (CHI) to Hamilton
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Highest demand for flights based on searches. 6% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Hamilton

Cheapest flights from Chicago to Hamilton
Explore the most affordable flight options available from Chicago to Hamilton. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This oojo deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/105:30 pmORD - YHM
1 stop30h 10mWestJet
Fri 10/176:00 amYHM - ORD
1 stop11h 43mWestJet
Deal found 9/15$273
This oojo deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/105:30 pmORD - YHM
1 stop30h 10mWestJet
Sun 10/126:00 amYHM - ORD
1 stop11h 43mWestJet
Deal found 9/15$276
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/142:20 pmORD - YHM
1 stop32h 35mMultiple Airlines
Sun 11/236:10 pmYHM - ORD
1 stop20h 25mMultiple Airlines
Deal found 9/14$281
This oojo deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/55:30 pmORD - YHM
1 stop30h 10mWestJet
Sat 10/186:00 amYHM - ORD
1 stop11h 43mWestJet
Deal found 9/15$288
This oojo deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/125:30 pmORD - YHM
1 stop30h 10mWestJet
Sat 10/186:00 amYHM - ORD
1 stop11h 43mWestJet
Deal found 9/16$304
This oojo deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/195:30 pmORD - YHM
1 stop30h 10mWestJet
Sun 10/266:10 pmYHM - ORD
1 stop20h 25mWestJet
Deal found 9/15$308
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:35 amORD - YHM
2 stops32h 42mMultiple Airlines
Sun 11/236:10 pmYHM - ORD
1 stop20h 25mMultiple Airlines
Deal found 9/14$337
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:30 pmORD - YHM
2 stops26h 48mMultiple Airlines
Sun 11/236:10 pmYHM - ORD
1 stop20h 25mMultiple Airlines
Deal found 9/14$357
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:35 amORD - YHM
2 stops39h 20mMultiple Airlines
Sun 11/236:10 pmYHM - ORD
1 stop20h 25mMultiple Airlines
Deal found 9/14$361
This Mytrip deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/55:30 pmORD - YHM
2 stops22h 14mMultiple Airlines
Sat 10/186:00 amYHM - ORD
1 stop11h 43mMultiple Airlines
Deal found 9/15$367

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Hamilton 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 2,558,603 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Chicago to Hamilton that are best for you.

Fly from

Chicago

Fly to

Hamilton

Route

Depart

Return

Price

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Fri 10/10

5:30 pm-12:40 am

1 stop30h 10m

Hamilton

Fri 10/17

6:00 am-4:43 pm

1 stop11h 43m

$279

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Fri 11/14

2:20 pm-11:55 pm

1 stop32h 35m

Hamilton

Sun 11/23

6:10 pm-1:35 pm

1 stop20h 25m

$281

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Sun 10/5

5:30 pm-12:40 am

1 stop30h 10m

Hamilton

Sat 10/18

6:00 am-4:43 pm

1 stop11h 43m

$288

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Sun 10/12

5:30 pm-12:40 am

1 stop30h 10m

Hamilton

Sat 10/18

6:00 am-4:43 pm

1 stop11h 43m

$304

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Wed 11/12

7:35 am-5:17 pm

2 stops32h 42m

Hamilton

Sun 11/23

6:10 pm-1:35 pm

1 stop20h 25m

$337

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Mon 11/10

6:30 pm-10:18 pm

2 stops26h 48m

Hamilton

Sun 11/23

6:10 pm-1:35 pm

1 stop20h 25m

$357

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Sat 11/15

5:45 pm-5:17 pm

2 stops46h 32m

Hamilton

Sun 11/23

6:10 pm-1:35 pm

1 stop20h 25m

$373

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Tue 11/11

12:37 pm-11:55 pm

2 stops34h 18m

Hamilton

Sun 11/23

6:10 pm-1:35 pm

1 stop20h 25m

$380

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Fri 11/14

2:20 pm-11:55 pm

1 stop32h 35m

Hamilton

Thu 11/20

6:10 pm-1:35 pm

1 stop20h 25m

$409

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Fri 11/14

2:20 pm-11:55 pm

1 stop32h 35m

Hamilton

Sat 11/22

2:35 pm-11:32 pm

2 stops33h 57m

$419

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 19 results
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Best time to book a flight from Chicago to Hamilton

Have a flexible travel schedule? Discover the best time to fly to Hamilton from Chicago 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 Chicago to Hamilton
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 Chicago to Hamilton. 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 into for flights to Hamilton from Chicago?

    Hamilton (YHM), located 6.8 mi from the city center, is the airport you fly into when you book flights from Chicago to Hamilton. 0 airlines have flights to Hamilton from Chicago on a regular basis. Booking flights from Chicago to Hamilton should not be difficult; the airport handles an average of 0 inbound flights from Chicago per day.

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

    For as low as $279, WestJet can have you in Hamilton, Ontario from Chicago in 30h 10m. The distance from Chicago to Hamilton, Ontario is about 414 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Hamilton 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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