S$102 Cheap Flights from Chicago to Toronto

View S$102 flight on Thu, 12 Feb, 2026Opens 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$102 for one-way flights and S$255 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Thu, 12 Feb - Wed, 18 Feb
ORD
Chicago
YYZ
Toronto
S$255 Return, found 1 day ago
S$255
Return
found 1 day ago
Select United flight, departing Thu, 12 Feb from Chicago to Toronto, returning Wed, 18 Feb, priced at S$255 found 1 day ago
Air Canada
Thu, 12 Feb - Wed, 18 Feb
ORD
Chicago
YYZ
Toronto
S$268 Return, found 1 day ago
S$268
Return
found 1 day ago
Select Air Canada flight, departing Thu, 12 Feb from Chicago to Toronto, returning Wed, 18 Feb, priced at S$268 found 1 day ago
United
Thu, 12 Feb - Wed, 18 Feb
ORD
Chicago
YYZ
Toronto
S$268 Return, found 1 day ago
S$268
Return
found 1 day ago
Select United flight, departing Thu, 12 Feb from Chicago to Toronto, returning Wed, 18 Feb, priced at S$268 found 1 day ago
Delta
Thu, 12 Feb - Wed, 18 Feb
ORD
Chicago
YYZ
Toronto
S$273 Return, found 1 day ago
S$273
Return
found 1 day ago
Select Delta flight, departing Thu, 12 Feb from Chicago to Toronto, returning Wed, 18 Feb, priced at S$273 found 1 day ago
United
Thu, 12 Feb - Wed, 18 Feb
ORD
Chicago
YYZ
Toronto
S$276 Return, found 1 day ago
S$276
Return
found 1 day ago
Select United flight, departing Thu, 12 Feb from Chicago to Toronto, returning Wed, 18 Feb, priced at S$276 found 1 day ago
United
Thu, 12 Feb - Wed, 18 Feb
ORD
Chicago
YYZ
Toronto
S$289 Return, found 1 day ago
S$289
Return
found 1 day ago
Select United flight, departing Thu, 12 Feb from Chicago to Toronto, returning Wed, 18 Feb, priced at S$289 found 1 day ago
Air Canada
Thu, 12 Feb - Wed, 18 Feb
ORD
Chicago
YYZ
Toronto
S$300 Return, found 1 day ago
S$300
Return
found 1 day ago
Select Air Canada flight, departing Thu, 12 Feb from Chicago to Toronto, returning Wed, 18 Feb, priced at S$300 found 1 day ago
Delta
Thu, 12 Feb - Wed, 18 Feb
ORD
Chicago
YYZ
Toronto
S$307 Return, found 1 day ago
S$307
Return
found 1 day ago
Select Delta flight, departing Thu, 12 Feb from Chicago to Toronto, returning Wed, 18 Feb, priced at S$307 found 1 day ago
Delta
Thu, 12 Feb - Wed, 18 Feb
ORD
Chicago
YYZ
Toronto
S$312 Return, found 1 day ago
S$312
Return
found 1 day ago
Select Delta flight, departing Thu, 12 Feb from Chicago to Toronto, returning Wed, 18 Feb, priced at S$312 found 1 day ago
American Airlines
Thu, 12 Feb - Wed, 18 Feb
ORD
Chicago
YYZ
Toronto
S$367 Return, found 1 day ago
S$367
Return
found 1 day ago
Select American Airlines flight, departing Thu, 12 Feb from Chicago to Toronto, returning Wed, 18 Feb, priced at S$367 found 1 day ago

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

September is typically the cheapest month to fly

From S$184 - S$549 per traveller.
Chicago to Toronto route information
Origin airport
O'Hare Intl.
Destination airport
Pearson Intl.
Return price
S$254
Distance
697 km

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, Delta, American Airlines, 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$102 and roundtrip prices from S$255*.
 

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$254.10

Hamilton

Kitchener

Chicago Airports

Chicago

*Available to Expedia members.