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

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Cheap Flights from Chicago to Toronto (ORD-YTO)

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
Air Canada
Sat, 16 Aug - Sat, 23 Aug
ORD
Chicago
YTZ
Toronto
S$269 Return, found 5 days ago
S$269
Return
found 5 days ago
Select Air Canada flight, departing Sat, 16 Aug from Chicago to Toronto, returning Sat, 23 Aug, priced at S$269 found 5 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
Air Canada
Sat, 16 Aug - Sat, 23 Aug
ORD
Chicago
YTZ
Toronto
S$277 Return, found 5 days ago
S$277
Return
found 5 days ago
Select Air Canada flight, departing Sat, 16 Aug from Chicago to Toronto, returning Sat, 23 Aug, priced at S$277 found 5 days ago
Air Canada
Thu, 14 Aug - Thu, 21 Aug
ORD
Chicago
YHM
Hamilton
S$278 Return, found 4 days ago
S$278
Return
found 4 days ago
Select Air Canada flight, departing Thu, 14 Aug from Chicago to Hamilton, returning Thu, 21 Aug, priced at S$278 found 4 days ago
Air Canada
Thu, 14 Aug - Thu, 21 Aug
ORD
Chicago
YKF
Kitchener
S$278 Return, found 4 days ago
S$278
Return
found 4 days ago
Select Air Canada flight, departing Thu, 14 Aug from Chicago to Kitchener, returning Thu, 21 Aug, priced at S$278 found 4 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
Air Canada
Fri, 15 Aug - Fri, 22 Aug
ORD
Chicago
YKF
Kitchener
S$278 Return, found 6 days ago
S$278
Return
found 6 days ago
Select Air Canada flight, departing Fri, 15 Aug from Chicago to Kitchener, 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
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

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

September is typically the cheapest month to fly

From S$176 - S$614 per traveller.

Graph displaying average flight prices per month

Chicago to Toronto route information
Origin airport
O'Hare Intl.
Destination airport
Pearson Intl.
Return price
S$247
Distance
697 km

Perfect flights from Chicago to Toronto

Your Journey from Chicago to Toronto

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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 YTO-All Airports 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 YTO-All Airports 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.

Explore a world of travel with Expedia

Toronto Airports

Toronto

Chicago to Pearson Intl.
S$246.90

London

Chicago to London Intl.
S$711.80

Kitchener

Hamilton

Chicago Airports

Chicago

*Available to Expedia members.