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Cheap flights from Hamilton, ON to Chicago from C$ 190

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 26/1. Fares are subject to change and may not be available on all flights or dates of travel.
YHM — CHI
13 Jan — 20 Jan1
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 14 December 2025.

Mon 22/127:25 a.m.YHM - ORD
1 stop12h 14mMultiple Airlines
Thu 25/125:00 a.m.ORD - YHM
1 stop9h 00mMultiple Airlines
Deal found 11/12C$ 1,209
Sun 28/127:25 a.m.YHM - ORD
1 stop18h 05mMultiple Airlines
Wed 31/125:00 a.m.ORD - YHM
1 stop9h 00mMultiple Airlines
Deal found 12/12C$ 1,429
Wed 24/127:00 a.m.YHM - ORD
2 stops37h 02mMultiple Airlines
Sun 28/124:44 p.m.ORD - YHM
1 stop21h 16mMultiple Airlines
Deal found 14/12C$ 1,520
Mon 15/127:25 a.m.YHM - ORD
1 stop17h 44mMultiple Airlines
Wed 24/125:00 a.m.ORD - YHM
1 stop9h 00mMultiple Airlines
Deal found 13/12C$ 1,897

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 14 December 2025.

Round-trip from

C$ 384

One-way from

C$ 190

Popular in

October

Cheapest in

September

Average price

C$ 435
28/1-4/2
  • 28/1-4/2
  • 2 total stops
  • 23h 23m total
  • Hamilton to Chicago
Search Deals
26/1
  • 26/1
  • 1 total stop
  • 14h 38m total
  • Hamilton to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 14 December 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

Wed 28/1

7:25 a.m.-9:03 p.m.

1 stop14h 38m

Chicago O'Hare Intl

Wed 4/2

5:15 a.m.-3:00 p.m.

1 stop8h 45m

C$ 384

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 25/1

7:25 a.m.-7:38 p.m.

1 stop13h 13m

Chicago O'Hare Intl

Wed 28/1

5:15 a.m.-3:00 p.m.

1 stop8h 45m

C$ 406

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Wed 7/1

7:25 a.m.-8:59 p.m.

1 stop14h 34m

Chicago O'Hare Intl

Wed 14/1

5:15 a.m.-3:00 p.m.

1 stop8h 45m

C$ 414

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Mon 26/1

7:25 a.m.-7:38 p.m.

1 stop13h 13m

Chicago O'Hare Intl

Mon 2/2

9:00 a.m.-11:35 p.m.

2 stops37h 35m

C$ 414

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Tue 27/1

5:45 a.m.-6:27 p.m.

2 stops37h 42m

Chicago O'Hare Intl

Tue 3/2

5:32 p.m.-3:00 p.m.

1 stop20h 28m

C$ 442

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sat 24/1

7:25 a.m.-9:03 p.m.

1 stop14h 38m

Chicago O'Hare Intl

Mon 26/1

5:15 a.m.-3:00 p.m.

1 stop8h 45m

C$ 474

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 9/1

7:00 a.m.-5:52 p.m.

1 stop11h 52m

Chicago O'Hare Intl

Fri 16/1

8:43 p.m.-8:55 p.m.

1 stop23h 12m

C$ 474

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Wed 28/1

7:25 a.m.-9:03 p.m.

1 stop14h 38m

C$ 226

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Mon 26/1

7:25 a.m.-10:46 p.m.

2 stops16h 21m

C$ 237

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 11/1

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

1 stop20h 25m

C$ 241

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/12

Showing 1-10 of 13 results
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

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

Currently, April is the cheapest month in which you can book a flight from Hamilton, Ontario to Chicago (average of C$ 113). Flying from Hamilton, Ontario to Chicago in February is currently the most expensive (average of C$ 253). 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.

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 14 December 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
10,525 reviews
Check prices

Entertainment

6.8

Boarding

7.3

Comfort

7.1

Crew

7.8

Food

6.3

Overall

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍
Air Canada
7.1
Good
10,525 reviews
Air Canada
7.1
Good
10,525 reviews
Check prices

Entertainment

6.8

Boarding

7.3

Comfort

7.1

Crew

7.8

Food

6.3

Overall

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍

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$ 300. Users have found that Air Canada is 24% 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, April is the cheapest month in which you can book a flight from Hamilton, Ontario to Chicago (average of C$ 113). Flying from Hamilton, Ontario to Chicago in February is currently the most expensive (average of C$ 253). 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 14 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 300AverageC$ 413FlexibilityNo 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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