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Cheap flights from Hamilton, ON to Chicago from C$ 175

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 24/2. Fares are subject to change and may not be available on all flights or dates of travel.
YHM — CHI
26 nov. — 3 dic.1
1 adult
1 adult, Economy, 0 bags

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 27 octubre 2025.

Round-trip from

C$ 483

One-way from

C$ 175

Popular in

March

Cheapest in

September

Average price

C$ 479
10/12-17/12
  • 10/12-17/12
  • 4 total stops
  • 27h 09m total
  • Hamilton to Chicago
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Air Canada
  • Air Canada
  • 24/2
  • 1 total stop
  • 5h 20m total
  • Hamilton to Chicago
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Highest demand for flights based on searches. 7% potential increase in price (C$ 43 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 17 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 27 octubre 2025.

mié. 10/127:00 a.m.YHM - ORD
3 stops18h 09mMultiple Airlines
mié. 17/125:00 a.m.ORD - YHM
1 stop9h 00mMultiple Airlines
Deal found 26/10C$ 483
jue. 11/126:10 p.m.YHM - ORD
1 stop20h 25mMultiple Airlines
jue. 18/1212:09 p.m.ORD - YHM
1 stop25h 11mMultiple Airlines
Deal found 26/10C$ 595
vie. 5/127:55 p.m.YHM - ORD
3 stops25h 06mMultiple Airlines
dom. 7/129:06 p.m.ORD - YHM
2 stops25h 41mMultiple Airlines
Deal found 26/10C$ 789
mar. 25/118:15 a.m.YHM - ORD
3 stops22h 17mMultiple Airlines
mar. 2/123:43 p.m.ORD - YHM
3 stops31h 04mMultiple Airlines
Deal found 26/10C$ 816

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 27 octubre 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

mié. 10/12

7:00 a.m.-12:09 a.m.

3 stops18h 09m

Chicago O'Hare Intl

mié. 17/12

5:00 a.m.-3:00 p.m.

1 stop9h 00m

C$ 483

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

jue. 11/12

6:10 p.m.-1:35 p.m.

1 stop20h 25m

Chicago O'Hare Intl

jue. 18/12

12:09 p.m.-2:20 p.m.

1 stop25h 11m

C$ 595

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

vie. 5/12

7:55 p.m.-8:01 p.m.

3 stops25h 06m

Chicago O'Hare Intl

dom. 7/12

9:06 p.m.-11:47 p.m.

2 stops25h 41m

C$ 789

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

mar. 25/11

8:15 a.m.-5:32 a.m.

3 stops22h 17m

Chicago O'Hare Intl

mar. 2/12

3:43 p.m.-11:47 p.m.

3 stops31h 04m

C$ 816

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

mar. 24/2

3:10 p.m.-7:30 p.m.

1 stop5h 20m

C$ 175

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

jue. 4/12

6:30 p.m.-10:05 p.m.

1 stop4h 35m

C$ 214

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

mié. 4/2

7:25 a.m.-11:42 p.m.

1 stop17h 17m

C$ 242

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

mié. 10/12

7:00 a.m.-12:09 a.m.

3 stops18h 09m

C$ 253

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

dom. 25/1

6:10 p.m.-1:35 p.m.

1 stop20h 25m

C$ 264

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

jue. 15/1

7:25 a.m.-11:42 p.m.

1 stop17h 17m

C$ 308

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/10

Showing 1-10 of 13 results
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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

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

Currently, June is the cheapest month in which you can book a flight from Hamilton, Ontario to Chicago (average of C$ 116). Flying from Hamilton, Ontario to Chicago in February is currently the most expensive (average of C$ 266). 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.

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 27 octubre 2025.
Read through reviews of airlines operating flights from Hamilton to Chicago, such as Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,370 reviews
Check prices

Food

6.3

Crew

7.8

Boarding

7.3

Overall

7.1

Entertainment

6.8

Comfort

7.1

Reviews

1 / 20
10.0
Excellent

janet,Sep 2025

YOW - YYZ

Really appreciated the leg room despite purchasing an economy ticket. Appreciated the extra complimentary wine. Nice touch. Was given immediate support without asking at check in, at the machine!! Ottawa's boarding was very organized with distinct rows in waiting room. Allowed for the main hall to not be blocked by people waiting to board.
Air Canada
7.1
Good
10,370 reviews
Air Canada
7.1
Good
10,370 reviews
Check prices

Food

6.3

Crew

7.8

Boarding

7.3

Overall

7.1

Entertainment

6.8

Comfort

7.1

Reviews

1 / 20
10.0
Excellent

janet,Sep 2025

YOW - YYZ

Really appreciated the leg room despite purchasing an economy ticket. Appreciated the extra complimentary wine. Nice touch. Was given immediate support without asking at check in, at the machine!! Ottawa's boarding was very organized with distinct rows in waiting room. Allowed for the main hall to not be blocked by people waiting to board.

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$ 308. Users have found that Air Canada is 19% cheaper than the other options available to this destination.

  • 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, June is the cheapest month in which you can book a flight from Hamilton, Ontario to Chicago (average of C$ 116). Flying from Hamilton, Ontario to Chicago in February is currently the most expensive (average of C$ 266). 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

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Alternative routes for Hamilton to Chicago

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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 27 octubre 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 308AverageC$ 385FlexibilityNo 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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