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$241+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YHM
Aug 24 — Aug 311
Mon 8/24
Mon 8/31
1 adult, Economy
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Cheap 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 July 25, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/22. 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 9/117:45 am
ORD
-
YHM
1 stop31h 10m
Multiple Airlines
Thu 9/176:10 pm
YHM
-
ORD
1 stop23h 30m
Multiple Airlines
Deal found 7/22$453
This Mytrip deal was found by Cheapflights users on 7/24. 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 9/275:30 pm
ORD
-
YHM
2 stops27h 39m
Multiple Airlines
Wed 9/307:00 am
YHM
-
ORD
2 stops34h 40m
Multiple Airlines
Deal found 7/24$526
This FlightHub deal was found by Cheapflights users on 7/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:30 pm
ORD
-
YHM
1 stop22h 45m
WestJet
Mon 9/146:10 pm
YHM
-
ORD
1 stop23h 30m
WestJet
Deal found 7/22$535
This FlightHub deal was found by Cheapflights users on 7/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:30 pm
ORD
-
YHM
1 stop22h 45m
WestJet
Sun 9/276:10 pm
YHM
-
ORD
1 stop23h 30m
WestJet
Deal found 7/23$543
This FlightHub deal was found by Cheapflights users on 7/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:30 pm
ORD
-
YHM
1 stop22h 45m
WestJet
Fri 9/46:10 pm
YHM
-
ORD
1 stop23h 30m
WestJet
Deal found 7/22$552
This Mytrip deal was found by Cheapflights users on 7/24. 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.
Tue 9/85:30 pm
ORD
-
YHM
2 stops20h 35m
Multiple Airlines
Tue 9/156:55 pm
YHM
-
ORD
2 stops22h 40m
Multiple Airlines
Deal found 7/24$559
This Justfly.com deal was found by Cheapflights users on 7/25. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:30 pm
ORD
-
YHM
1 stop22h 45m
WestJet
Sun 9/136:10 pm
YHM
-
ORD
1 stop23h 30m
WestJet
Deal found 7/25$589

Find 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 July 25, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$453
(Kiwi.com)

One-way from

$241
(FlightHub)

Popular in

August

Cheapest in

March

Average price

$303
Provider with most accurate pricing for Chicago (CHI)-Hamilton flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Hamilton flights.
Search Deals
From Chicago (CHI) to Hamilton
Search Deals
One-way flight from Chicago (CHI) to Hamilton
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 July 25, 2026.
Use the filters below to find and compare flights from Chicago to Hamilton that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Thu 9/24

5:30 pm-5:15 pm

1 stop22h 45m

Hamilton

Sun 9/27

6:10 pm-4:40 pm

1 stop23h 30m

$548

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Tue 9/8

5:30 pm-3:05 pm

2 stops20h 35m

Hamilton

Tue 9/15

6:55 pm-4:35 pm

2 stops22h 40m

$559

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Thu 9/24

5:30 pm-5:15 pm

1 stop22h 45m

Hamilton

Wed 9/30

6:10 pm-4:40 pm

1 stop23h 30m

$598

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Thu 9/10

5:30 pm-5:15 pm

1 stop22h 45m

Hamilton

Sun 9/13

6:10 pm-4:40 pm

1 stop23h 30m

$603

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Wed 8/19

5:30 pm-5:15 pm

1 stop22h 45m

Hamilton

Wed 8/26

6:10 pm-4:40 pm

1 stop23h 30m

$608
Quickest round-trip

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Fri 10/16

7:17 pm-3:55 pm

2 stops19h 38m

Hamilton

Mon 10/19

8:15 am-6:38 pm

2 stops11h 23m

$758

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Mon 8/17

5:30 pm-8:30 pm

3 stops26h 00m

Hamilton

Sun 8/23

6:05 am-4:40 pm

3 stops35h 35m

$820

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Thu 8/13

5:30 pm-3:08 pm

2 stops20h 38m

Hamilton

Mon 8/17

6:55 pm-1:10 pm

3 stops19h 15m

$823

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Fri 9/11

5:30 pm-10:34 pm

2 stops28h 04m

Hamilton

Mon 9/21

5:45 pm-4:40 pm

2 stops23h 55m

$910
Cheapest one-way

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Sun 10/11

5:30 pm-5:35 pm

3 stops23h 05m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/21

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3
  • Most accurate provider: When it comes to deals on Chicago-Hamilton, Ontario flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Chicago-Hamilton, Ontario flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Chicago-Hamilton, Ontario flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Hamilton, Ontario flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Hamilton, Ontario flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 $548, WestJet can have you in Hamilton, Ontario from Chicago in 22h 45m. 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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