S$157 Cheap Flights from Hamilton to Chicago

View S$157 flight on Sat, 23 Aug, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Hamilton to Chicago (YHM-ORD)

Prices were available within the past 7 days and start at S$157 for one-way flights and S$268 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, 28 Aug - Thu, 4 Sep
YHM
Hamilton
ORD
Chicago
S$268 Return, found 4 days ago
S$268
Return
found 4 days ago
Select Air Canada flight, departing Thu, 28 Aug from Hamilton to Chicago, returning Thu, 4 Sep, priced at S$268 found 4 days ago
Air Canada
Fri, 29 Aug - Fri, 5 Sep
YHM
Hamilton
ORD
Chicago
S$279 Return, found 2 days ago
S$279
Return
found 2 days ago
Select Air Canada flight, departing Fri, 29 Aug from Hamilton to Chicago, returning Fri, 5 Sep, priced at S$279 found 2 days ago
Air Canada
Tue, 10 Feb - Fri, 13 Feb
YHM
Hamilton
ORD
Chicago
S$336 Return, found 6 days ago
S$336
Return
found 6 days ago
Select Air Canada flight, departing Tue, 10 Feb from Hamilton to Chicago, returning Fri, 13 Feb, priced at S$336 found 6 days ago
Air Canada
Thu, 28 Aug - Thu, 4 Sep
YHM
Hamilton
ORD
Chicago
S$366 Return, found 4 days ago
S$366
Return
found 4 days ago
Select Air Canada flight, departing Thu, 28 Aug from Hamilton to Chicago, returning Thu, 4 Sep, priced at S$366 found 4 days ago
Air Canada
Fri, 29 Aug - Fri, 5 Sep
YHM
Hamilton
ORD
Chicago
S$377 Return, found 2 days ago
S$377
Return
found 2 days ago
Select Air Canada flight, departing Fri, 29 Aug from Hamilton to Chicago, returning Fri, 5 Sep, priced at S$377 found 2 days ago
Air Canada
Tue, 29 Jul - Sun, 3 Aug
YHM
Hamilton
ORD
Chicago
S$474 Return, found 3 days ago
S$474
Return
found 3 days ago
Select Air Canada flight, departing Tue, 29 Jul from Hamilton to Chicago, returning Sun, 3 Aug, priced at S$474 found 3 days ago
Air Canada
Tue, 10 Feb - Fri, 13 Feb
YHM
Hamilton
ORD
Chicago
S$497 Return, found 6 days ago
S$497
Return
found 6 days ago
Select Air Canada flight, departing Tue, 10 Feb from Hamilton to Chicago, returning Fri, 13 Feb, priced at S$497 found 6 days ago
Air Canada
Tue, 5 Aug - Fri, 8 Aug
YHM
Hamilton
ORD
Chicago
S$499 Return, found 1 day ago
S$499
Return
found 1 day ago
Select Air Canada flight, departing Tue, 5 Aug from Hamilton to Chicago, returning Fri, 8 Aug, priced at S$499 found 1 day ago
Air Canada
Tue, 29 Jul - Sun, 3 Aug
YHM
Hamilton
ORD
Chicago
S$502 Return, found 3 days ago
S$502
Return
found 3 days ago
Select Air Canada flight, departing Tue, 29 Jul from Hamilton to Chicago, returning Sun, 3 Aug, priced at S$502 found 3 days ago
Air Canada
Mon, 25 Aug - Mon, 1 Sep
YHM
Hamilton
ORD
Chicago
S$534 Return, found 6 days ago
S$534
Return
found 6 days ago
Select Air Canada flight, departing Mon, 25 Aug from Hamilton to Chicago, returning Mon, 1 Sep, priced at S$534 found 6 days ago
Hamilton to Chicago route information
Origin airport
John C. Munro Hamilton Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada
Return price
S$268
Distance
662 km

Perfect flights from Hamilton to Chicago

Your Journey from Hamilton to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Hamilton to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Air Canada. Our selection of flights from John C. Munro Hamilton Intl. to O'Hare Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Hamilton to Chicago Flights

Experience the joy of finding cheap flights from John C. Munro Hamilton Intl. to O'Hare Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$157 and roundtrip prices from S$268*.
 

Pre-Flight Essentials

Ensure a smooth journey from Hamilton to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Hamilton to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Hamilton to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Hamilton to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Hamilton to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from YHM to ORD?
If you're planning on travelling from YHM to O'Hare Intl. Airport (ORD), round-trip flights start from S$268. This price is based on fares quoted within the last 7 days on Expedia for flights departing within the next year, so don't let a good deal pass you by. Book now and save yourself both money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Toronto Hamilton Intl. Airport to O'Hare Airport?
When it comes to cancellation fees, every airline has its own terms and conditions. If you decide to cancel your escape, visit our Customer Service Portal.
How do I find cheap flights from YHM to O'Hare Intl. Airport (ORD) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for John C. Munro Hamilton Intl. Airport (YHM) to O'Hare Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from YHM to O'Hare Intl. Airport (ORD)?
It's just 670 kilometres between Hamilton and Chicago. Chances are you'll spend more time travelling to and from the airport than actually flying!
Which airlines fly direct from YHM to ORD?
You won't find any airlines operating directly between Toronto Hamilton Intl. Airport and O'Hare Airport, so be ready to make at least one stop on your journey. A layover, whether short or long, can be a good way to break up a trip!
Are John C. Munro Hamilton Intl. Airport (YHM) to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
Booking your trip from John C. Munro Hamilton Intl. Airport (YHM) to O'Hare Intl. Airport (ORD) last minute could be your ticket to an awesome deal. However, you might miss out on a flight altogether! If you'd rather avoid the risk, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains up to 12 months in advance. If your preferred carrier hasn't released tickets yet, check back frequently as deals are updated all the time on Expedia.

Explore a world of travel with Expedia

*Available to Expedia members.