$106 Cheap Flights from Hamilton (YHM) to Chicago (ORD)

View $106 flight on Mon, Jun 2, 2025Opens in a new window

Popular airlines from John C. Munro Hamilton Intl. Airport (YHM) to Chicago O'Hare Intl. Airport (ORD)

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Find available prices by choosing your travel dates.

Cheap Flights from Hamilton to Chicago (YHM-ORD)

Prices were available within the past 7 days and start at $106 for one-way flights and $162 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Wed, Jul 2 - Sun, Jul 6
YHM
Hamilton
ORD
Chicago
$162 Roundtrip, found 2 days ago
$162
Roundtrip
found 2 days ago
Select Air Canada flight, departing Wed, Jul 2 from Hamilton to Chicago, returning Sun, Jul 6, priced at $162 found 2 days ago
Air Canada
Fri, May 9 - Mon, May 12
YHM
Hamilton
ORD
Chicago
$202 Roundtrip, found 2 days ago
$202
Roundtrip
found 2 days ago
Select Air Canada flight, departing Fri, May 9 from Hamilton to Chicago, returning Mon, May 12, priced at $202 found 2 days ago
Air Canada
Wed, Jul 2 - Sun, Jul 6
YHM
Hamilton
ORD
Chicago
$219 Roundtrip, found 2 days ago
$219
Roundtrip
found 2 days ago
Select Air Canada flight, departing Wed, Jul 2 from Hamilton to Chicago, returning Sun, Jul 6, priced at $219 found 2 days ago
Air Canada
Fri, May 2 - Sun, May 11
YHM
Hamilton
ORD
Chicago
$231 Roundtrip, found 2 days ago
$231
Roundtrip
found 2 days ago
Select Air Canada flight, departing Fri, May 2 from Hamilton to Chicago, returning Sun, May 11, priced at $231 found 2 days ago
Air Canada
Sat, Jun 7 - Mon, Jun 9
YHM
Hamilton
ORD
Chicago
$232 Roundtrip, found 2 days ago
$232
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, Jun 7 from Hamilton to Chicago, returning Mon, Jun 9, priced at $232 found 2 days ago
Air Canada
Fri, May 23 - Mon, May 26
YHM
Hamilton
ORD
Chicago
$233 Roundtrip, found 2 hours ago
$233
Roundtrip
found 2 hours ago
Select Air Canada flight, departing Fri, May 23 from Hamilton to Chicago, returning Mon, May 26, priced at $233 found 2 hours ago
Air Canada
Sun, Jul 27 - Thu, Jul 31
YHM
Hamilton
ORD
Chicago
$240 Roundtrip, found 13 hours ago
$240
Roundtrip
found 13 hours ago
Select Air Canada flight, departing Sun, Jul 27 from Hamilton to Chicago, returning Thu, Jul 31, priced at $240 found 13 hours ago
Air Canada
Sun, Jul 27 - Thu, Jul 31
YHM
Hamilton
ORD
Chicago
$248 Roundtrip, found 13 hours ago
$248
Roundtrip
found 13 hours ago
Select Air Canada flight, departing Sun, Jul 27 from Hamilton to Chicago, returning Thu, Jul 31, priced at $248 found 13 hours ago
Air Canada
Mon, Sep 1 - Tue, Sep 30
YHM
Hamilton
ORD
Chicago
$255 Roundtrip, found 4 days ago
$255
Roundtrip
found 4 days ago
Select Air Canada flight, departing Mon, Sep 1 from Hamilton to Chicago, returning Tue, Sep 30, priced at $255 found 4 days ago
WestJet
Wed, Jun 11 - Wed, Jun 18
YHM
Hamilton
ORD
Chicago
$1,358 Roundtrip, found 15 hours ago
$1,358
Roundtrip
found 15 hours ago
Select WestJet flight, departing Wed, Jun 11 from Hamilton to Chicago, returning Wed, Jun 18, priced at $1,358 found 15 hours ago
Flights from Hamilton (YHM) to Chicago (ORD)
Origin airport
John C. Munro Hamilton Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, WestJet
Roundtrip price
$161
Distance
413 mi

Hamilton to Chicago Flights

The cheapest times to fly from Hamilton to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Hamilton to Chicago are during the month of July. You can find some of the cheapest flights from Hamilton to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Hamilton to Chicago

Sunday is one of the best days to book for cheap flights from Hamilton to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Hamilton to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Hamilton to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $106 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Hamilton to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Hamilton to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from John C. Munro Hamilton Intl. Airport (YHM) to O'Hare Intl. Airport (ORD) cost?
Discover the latest flight deals from YHM to ORD by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from YHM to ORD?
The cheapest flights from YHM to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from John C. Munro Hamilton Intl. Airport (YHM) to O'Hare Intl. Airport (ORD)?
Although Hamilton, ON (YHM-John C. Munro Hamilton Intl.) doesn’t offer any direct flights to O’Hare Intl. Airport (ORD), other airports have nonstop options. Traveling from Pearson Intl. Airport (YYZ) will get you to Chicago without any detours.
What is the cheapest airline that flies from YHM to ORD?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from YHM to ORD. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from John C. Munro Hamilton Intl. Airport (YHM) to O'Hare Intl. Airport (ORD)?
You’ll need to catch a flight with a layover when traveling from John C. Munro Hamilton Intl. Airport (YHM) to O’Hare Intl. Airport (ORD). Direct flights don’t operate daily on this route. However, simply filter your search to include one or two stops to find an option that works for you.
What day of the week has the most flights from YHM to ORD?
Typically you’ll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* But this can vary based on the season, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from John C. Munro Hamilton Intl. Airport (YHM) to O'Hare Intl. Airport (ORD)?
To arrive at O’Hare Intl. Airport (ORD) on schedule, choose a flight that leaves from John C. Munro Hamilton Intl. Airport (YHM) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
Is it cheaper to buy a plane ticket from John C. Munro Hamilton Intl. Airport (YHM) to O'Hare Intl. Airport (ORD) last-minute?
Waiting until just before your trip to book your flight from YHM to ORD often results in higher prices. While it’s possible to find some last-minute offers, they aren’t always guaranteed. Be flexible with your travel plans to maximize your chances of getting a bargain.
Is it cheaper to book a YHM to ORD flight and hotel package?
You’ll generally save money by securing a YHM to ORD flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it’s simple to manage everything in one convenient place. After choosing your ideal accommodations and flights, consider adding extras such as activities, car rentals and tours.
Can I cancel or change the date of my flight from John C. Munro Hamilton Intl. Airport (YHM) to O'Hare Intl. Airport (ORD)?
If you booked your YHM to ORD flight within the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for further details.

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*Available to One Key members.