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Cheap flights from Hamilton, ON to Chicago from C$ 280

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 21/7. Fares are subject to change and may not be available on all flights or dates of travel.
YHM — CHI
17 Jun — 24 Jun1
1 adult

Cheap 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 2025.

Round-trip from

C$ 535

One-way from

C$ 280

Popular in

February

Cheapest in

June

Average price

C$ 306
11/7-13/7
  • 11/7-13/7
  • 5 total stops
  • 65h 36m total
  • Hamilton to Chicago
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21/7
  • 21/7
  • 3 total stops
  • 25h 03m total
  • Hamilton to Chicago
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Highest demand for flights based on searches. 20% potential increase in price (C$ 133 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 19 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Hamilton to Chicago

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 2025.

Fri 11/76:00 a.m.YHM - ORD
3 stops33h 13mMultiple Airlines
Sun 13/73:18 p.m.ORD - YHM
2 stops32h 23mMultiple Airlines
Deal found 10/6C$ 535
Sat 6/96:00 a.m.YHM - ORD
1 stop11h 43mWestJet
Tue 9/95:30 p.m.ORD - YHM
1 stop30h 10mWestJet
Deal found 11/6C$ 722

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 2025.
Use the filters below to find and compare flights from Hamilton to Chicago that are best for you.

Fly from

Hamilton

Fly to

Chicago

Route

Depart

Return

Price

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 11/7

6:00 a.m.-2:13 p.m.

3 stops33h 13m

Chicago O'Hare Intl

Sun 13/7

3:18 p.m.-12:41 a.m.

2 stops32h 23m

C$ 535

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sat 6/9

6:00 a.m.-4:43 p.m.

1 stop11h 43m

Chicago O'Hare Intl

Tue 9/9

5:30 p.m.-12:40 a.m.

1 stop30h 10m

C$ 722

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Mon 21/7

6:00 a.m.-6:03 a.m.

3 stops25h 03m

C$ 280

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Mon 8/9

6:00 a.m.-4:43 p.m.

1 stop11h 43m

C$ 346

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

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

What is the cheapest month to book a flight from Hamilton, Ontario to Chicago?

Currently, January is the cheapest month in which you can book a flight from Hamilton, Ontario to Chicago (average of C$ 261). Flying from Hamilton, Ontario to Chicago in March is currently the most expensive (average of C$ 352). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 12 June 2025.
WestJet
7.2
Good
2,868 reviews
Check prices

Boarding

7.4

Comfort

7.1

Entertainment

6.1

Overall

7.2

Food

6.2

Crew

7.9

Reviews

1 / 20
6.0
Good

Deb,Jan 2025

YYZ - YYC

Boarding went smoothly, you didn't accept debit card for food on flight
WestJet
7.2
Good
2,868 reviews
WestJet
7.2
Good
2,868 reviews
Check prices

Boarding

7.4

Comfort

7.1

Entertainment

6.1

Overall

7.2

Food

6.2

Crew

7.9

Reviews

1 / 20
6.0
Good

Deb,Jan 2025

YYZ - YYC

Boarding went smoothly, you didn't accept debit card for food on flight
Air Canada
7.1
Good
9,537 reviews
WestJet
7.2
Good
2,868 reviews
Check prices

Boarding

7.4

Comfort

7.1

Entertainment

6.1

Overall

7.2

Food

6.2

Crew

7.9

Reviews

1 / 20
6.0
Good

Deb,Jan 2025

YYZ - YYC

Boarding went smoothly, you didn't accept debit card for food on flight

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 WestJet is currently your cheapest option to Chicago, with prices starting at C$ 722.

  • 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.

  • What is the cheapest month to book a flight from Hamilton, Ontario to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Hamilton, Ontario to Chicago (average of C$ 261). Flying from Hamilton, Ontario to Chicago in March is currently the most expensive (average of C$ 352). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Hamilton to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 301AverageC$ 368FlexibilityNo 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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