S$95 Cheap Flights from Chicago to Toronto

View S$95 flight on Sun, 9 Nov, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Toronto Pearson Intl. Airport (YYZ)

  • 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 Chicago to Toronto (ORD-YYZ)

Prices were available within the past 7 days and start at S$95 for one-way flights and S$253 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sat, 1 Nov - Sun, 16 Nov
ORD
Chicago
YYZ
Toronto
S$253 Return, found 4 days ago
S$253
Return
found 4 days ago
Select United flight, departing Sat, 1 Nov from Chicago to Toronto, returning Sun, 16 Nov, priced at S$253 found 4 days ago
Air Canada
Sun, 9 Nov - Sun, 16 Nov
ORD
Chicago
YYZ
Toronto
S$253 Return, found 1 day ago
S$253
Return
found 1 day ago
Select Air Canada flight, departing Sun, 9 Nov from Chicago to Toronto, returning Sun, 16 Nov, priced at S$253 found 1 day ago
Air Canada
Sun, 9 Nov - Sun, 16 Nov
ORD
Chicago
YYZ
Toronto
S$261 Return, found 1 day ago
S$261
Return
found 1 day ago
Select Air Canada flight, departing Sun, 9 Nov from Chicago to Toronto, returning Sun, 16 Nov, priced at S$261 found 1 day ago
Air Canada
Sun, 9 Nov - Sun, 16 Nov
ORD
Chicago
YYZ
Toronto
S$266 Return, found 1 day ago
S$266
Return
found 1 day ago
Select Air Canada flight, departing Sun, 9 Nov from Chicago to Toronto, returning Sun, 16 Nov, priced at S$266 found 1 day ago
Air Canada
Sun, 26 Oct - Tue, 4 Nov
ORD
Chicago
YYZ
Toronto
S$272 Return, found 4 days ago
S$272
Return
found 4 days ago
Select Air Canada flight, departing Sun, 26 Oct from Chicago to Toronto, returning Tue, 4 Nov, priced at S$272 found 4 days ago
American Airlines
Thu, 23 Oct - Mon, 27 Oct
ORD
Chicago
YYZ
Toronto
S$275 Return, found 22 hours ago
S$275
Return
found 22 hours ago
Select American Airlines flight, departing Thu, 23 Oct from Chicago to Toronto, returning Mon, 27 Oct, priced at S$275 found 22 hours ago
Delta
Thu, 23 Oct - Mon, 27 Oct
ORD
Chicago
YYZ
Toronto
S$280 Return, found 22 hours ago
S$280
Return
found 22 hours ago
Select Delta flight, departing Thu, 23 Oct from Chicago to Toronto, returning Mon, 27 Oct, priced at S$280 found 22 hours ago
Air Canada
Sat, 25 Oct - Tue, 4 Nov
ORD
Chicago
YYZ
Toronto
S$280 Return, found 4 days ago
S$280
Return
found 4 days ago
Select Air Canada flight, departing Sat, 25 Oct from Chicago to Toronto, returning Tue, 4 Nov, priced at S$280 found 4 days ago
Air Canada
Thu, 23 Oct - Mon, 27 Oct
ORD
Chicago
YYZ
Toronto
S$282 Return, found 22 hours ago
S$282
Return
found 22 hours ago
Select Air Canada flight, departing Thu, 23 Oct from Chicago to Toronto, returning Mon, 27 Oct, priced at S$282 found 22 hours ago
Delta
Thu, 23 Oct - Mon, 27 Oct
ORD
Chicago
YYZ
Toronto
S$287 Return, found 22 hours ago
S$287
Return
found 22 hours ago
Select Delta flight, departing Thu, 23 Oct from Chicago to Toronto, returning Mon, 27 Oct, priced at S$287 found 22 hours ago

Find the cheapest month to fly from Chicago (ORD) to Toronto (YYZ)

October is typically the cheapest month to fly

From S$192 - S$344 per traveller.

Graph displaying average flight prices per month

Chicago to Toronto route information
Origin airport
O'Hare Intl.
Destination airport
Pearson Intl.
Airlines serving
Air Canada, American Airlines, Delta, United
Return price
S$252
Distance
697 km
Average flight time
2 hours 43 mins

Perfect flights from Chicago to Toronto

Your Journey from Chicago to Toronto

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to Toronto 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, American Airlines, Delta, United. Our selection of flights from O'Hare Intl. to Pearson 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 Chicago to Toronto Flights

Experience the joy of finding cheap flights from O'Hare Intl. to Pearson Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$95 and roundtrip prices from S$253*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to Toronto 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 Toronto

Picture yourself stepping off the plane in Toronto and immersing yourself in the unique atmosphere of Toronto. 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 Chicago to Toronto 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 Chicago to Toronto.
 

Beyond the Flight – Exploring Toronto

With Expedia, your adventure extends beyond the flight. Explore Toronto 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 Chicago to Toronto 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 Chicago to Toronto 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 O'Hare Intl. Airport (ORD) to Toronton Pearson?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price available for a round-trip journey between O'Hare Intl. Airport (ORD) and YYZ was S$253. Fares this good don't stick around for long, so book yours today. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Intl. Airport (ORD) to Pearson Intl. Airport (YYZ)?
Every air carrier has its own set of terms and conditions. If you do decide to cancel, follow the instructions on our Customer Service Portal.
How do I find cheap flights from ORD to YYZ 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 O'Hare Intl. Airport (ORD) to YYZ flights, you'll see a "no change fees" filter for you to select.
How far is the flight from ORD to Toronton Pearson?
It's just 700 kilometres between Chicago and Mississauga. Chances are you'll spend more time travelling to and from the airport than actually flying!
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Toronto Pearson Airport?
A leading airline that services the route from O'Hare Airport to Toronton Pearson is American Airlines (AA). It offers 152 flights monthly. Offering 147 flights each month along this route, United Airlines (UA) is another traveller favourite.
Are ORD to Toronton Pearson flight tickets cheaper when they're purchased at the last minute?
Booking last minute from ORD to Toronto Pearson Airport can be hit-or-miss. You might be lucky and score a bargain, but you could also miss out entirely! If you'd rather start planning your trip early, Expedia compares flight deals up to 12 months in advance. Just remember that not all airlines issue their prices so far in advance. Our top tip? Check back often as prices are updated regularly.

Explore a world of travel with Expedia

Toronto Airports

Toronto

Hamilton

Kitchener

Chicago Airports

Chicago

*Available to Expedia members.