S$100 Cheap Flights from Chicago to Toronto

View S$100 flight on Tue, 7 Oct, 2025Opens in a new window

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

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Cheap Flights from Chicago to Toronto (ORD-YYZ)

Prices were available within the past 7 days and start at S$100 for one-way flights and S$263 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Thu, 14 Aug - Thu, 21 Aug
ORD
Chicago
YYZ
Toronto
S$263 Return, found 3 days ago
S$263
Return
found 3 days ago
Select United flight, departing Thu, 14 Aug from Chicago to Toronto, returning Thu, 21 Aug, priced at S$263 found 3 days ago
United
Thu, 14 Aug - Thu, 21 Aug
ORD
Chicago
YYZ
Toronto
S$270 Return, found 3 days ago
S$270
Return
found 3 days ago
Select United flight, departing Thu, 14 Aug from Chicago to Toronto, returning Thu, 21 Aug, priced at S$270 found 3 days ago
American Airlines
Thu, 14 Aug - Thu, 21 Aug
ORD
Chicago
YYZ
Toronto
S$278 Return, found 3 days ago
S$278
Return
found 3 days ago
Select American Airlines flight, departing Thu, 14 Aug from Chicago to Toronto, returning Thu, 21 Aug, priced at S$278 found 3 days ago
United
Fri, 15 Aug - Fri, 22 Aug
ORD
Chicago
YYZ
Toronto
S$278 Return, found 6 days ago
S$278
Return
found 6 days ago
Select United flight, departing Fri, 15 Aug from Chicago to Toronto, returning Fri, 22 Aug, priced at S$278 found 6 days ago
American Airlines
Thu, 14 Aug - Thu, 21 Aug
ORD
Chicago
YYZ
Toronto
S$285 Return, found 3 days ago
S$285
Return
found 3 days ago
Select American Airlines flight, departing Thu, 14 Aug from Chicago to Toronto, returning Thu, 21 Aug, priced at S$285 found 3 days ago
Air Canada
Fri, 15 Aug - Fri, 22 Aug
ORD
Chicago
YYZ
Toronto
S$293 Return, found 6 days ago
S$293
Return
found 6 days ago
Select Air Canada flight, departing Fri, 15 Aug from Chicago to Toronto, returning Fri, 22 Aug, priced at S$293 found 6 days ago
United
Thu, 14 Aug - Thu, 21 Aug
ORD
Chicago
YYZ
Toronto
S$295 Return, found 3 days ago
S$295
Return
found 3 days ago
Select United flight, departing Thu, 14 Aug from Chicago to Toronto, returning Thu, 21 Aug, priced at S$295 found 3 days ago
Delta
Thu, 14 Aug - Thu, 21 Aug
ORD
Chicago
YYZ
Toronto
S$295 Return, found 3 days ago
S$295
Return
found 3 days ago
Select Delta flight, departing Thu, 14 Aug from Chicago to Toronto, returning Thu, 21 Aug, priced at S$295 found 3 days ago
Delta
Fri, 15 Aug - Fri, 22 Aug
ORD
Chicago
YYZ
Toronto
S$300 Return, found 6 days ago
S$300
Return
found 6 days ago
Select Delta flight, departing Fri, 15 Aug from Chicago to Toronto, returning Fri, 22 Aug, priced at S$300 found 6 days ago
Delta
Thu, 14 Aug - Thu, 21 Aug
ORD
Chicago
YYZ
Toronto
S$302 Return, found 3 days ago
S$302
Return
found 3 days ago
Select Delta flight, departing Thu, 14 Aug from Chicago to Toronto, returning Thu, 21 Aug, priced at S$302 found 3 days ago

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

October is typically the cheapest month to fly

From S$176 - S$613 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$247
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, United, American Airlines, Delta, WestJet. 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$100 and roundtrip prices from S$263*.
 

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 . 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$263. 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.

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