Find flights
When to book
Airlines
FAQs

Cheap flights from Hamilton, ON to Chicago from C$ 218

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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
YHM — CHI
28 May — 4 Jun1
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 28 April 2026.

Sat 6/68:15 a.m.
YHM
-
ORD
1 stop16h 00m
Multiple Airlines
Sat 13/65:05 a.m.
ORD
-
YHM
1 stop9h 50m
Multiple Airlines
Deal found 22/4C$ 503
Mon 8/68:15 a.m.
YHM
-
ORD
1 stop29h 10m
Multiple Airlines
Mon 15/65:05 a.m.
ORD
-
YHM
1 stop9h 50m
Multiple Airlines
Deal found 25/4C$ 590
Sat 16/58:15 a.m.
YHM
-
ORD
1 stop16h 00m
Multiple Airlines
Mon 18/55:05 a.m.
ORD
-
YHM
1 stop9h 50m
Multiple Airlines
Deal found 27/4C$ 593
Thu 21/57:00 a.m.
YHM
-
ORD
2 stops34h 40m
Multiple Airlines
Sun 24/55:30 p.m.
ORD
-
YHM
2 stops27h 44m
Multiple Airlines
Deal found 26/4C$ 701
Fri 22/57:00 a.m.
YHM
-
ORD
2 stops34h 40m
Multiple Airlines
Tue 26/55:30 p.m.
ORD
-
YHM
2 stops27h 39m
Multiple Airlines
Deal found 27/4C$ 703
Sat 23/58:15 a.m.
YHM
-
ORD
2 stops24h 40m
Multiple Airlines
Sat 30/55:30 p.m.
ORD
-
YHM
1 stop28h 48m
Multiple Airlines
Deal found 25/4C$ 717
Fri 22/57:00 a.m.
YHM
-
ORD
2 stops34h 40m
Multiple Airlines
Mon 25/55:30 p.m.
ORD
-
YHM
2 stops27h 39m
Multiple Airlines
Deal found 27/4C$ 725
Sun 24/57:55 p.m.
YHM
-
ORD
1 stop21h 45m
Multiple Airlines
Sun 31/55:30 p.m.
ORD
-
YHM
1 stop28h 43m
Multiple Airlines
Deal found 26/4C$ 776

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 28 April 2026.

Round-trip from

C$ 590

One-way from

C$ 218

Popular in

October

Cheapest in

September

Average price

C$ 454
8/6-15/6
  • 8/6-15/6
  • 2 total stops
  • 39h 00m total
  • Hamilton to Chicago
Search Deals
Air Canada
  • Air Canada
  • 12/7
  • 1 total stop
  • 4h 30m total
  • Hamilton to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

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 28 April 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

Mon 8/6

8:15 a.m.-8:03 a.m.

2 stops24h 48m

Chicago O'Hare Intl

Mon 15/6

5:05 a.m.-3:55 p.m.

1 stop9h 50m

C$ 645

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Wed 27/5

7:55 p.m.-4:40 p.m.

1 stop21h 45m

Chicago O'Hare Intl

Tue 2/6

9:37 p.m.-11:13 p.m.

2 stops24h 36m

C$ 761

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Tue 9/6

7:55 p.m.-4:40 p.m.

1 stop21h 45m

Chicago O'Hare Intl

Tue 16/6

5:30 p.m.-11:13 p.m.

1 stop28h 43m

C$ 872
Quickest round-trip

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sat 16/5

8:15 a.m.-11:15 p.m.

1 stop16h 00m

Chicago O'Hare Intl

Mon 18/5

5:05 a.m.-3:55 p.m.

1 stop9h 50m

C$ 987

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 20/8

7:00 a.m.-4:40 p.m.

2 stops34h 40m

Chicago O'Hare Intl

Sun 23/8

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

2 stops27h 39m

C$ 999

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 14/8

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

3 stops20h 27m

Chicago O'Hare Intl

Sat 15/8

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

2 stops20h 38m

C$ 1,210

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 23/7

7:00 a.m.-4:40 p.m.

2 stops34h 40m

Chicago O'Hare Intl

Fri 31/7

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

3 stops25h 55m

C$ 1,213

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Wed 1/7

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

3 stops25h 50m

Chicago O'Hare Intl

Sat 4/7

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

3 stops22h 55m

C$ 1,279
Cheapest one-way

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Tue 26/5

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

1 stop23h 30m

C$ 305

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 29/5

7:00 a.m.-4:40 p.m.

2 stops34h 40m

C$ 324

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/4

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

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

How much does it cost to fly round-trip from Hamilton, Ontario to Chicago?

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 28 April 2026.
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
10,975 reviews
Check prices

Overall

7.1

Boarding

7.3

Comfort

7.1

Crew

7.8

Food

6.3

Entertainment

6.8

Reviews

1 / 20
6.0
Good

Thomas,Apr 2026

YYZ - LHR

Food is sub par. I travel a lot and AC food is not good
Air Canada
7.1
Good
10,975 reviews
Air Canada
7.1
Good
10,975 reviews
Check prices

Overall

7.1

Boarding

7.3

Comfort

7.1

Crew

7.8

Food

6.3

Entertainment

6.8

Reviews

1 / 20
6.0
Good

Thomas,Apr 2026

YYZ - LHR

Food is sub par. I travel a lot and AC food is not good

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$ 264. Users have found that Air Canada is 28% 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 28 April 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 264AverageC$ 468FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.