S$111 Cheap Flights from Chicago to Toronto

View S$111 flight on Sun, 3 Aug, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Billy Bishop Toronto City Airport (YTZ)

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Cheap Flights from Chicago to Toronto (MDW-YTZ)

Prices were available within the past 7 days and start at S$111 for one-way flights and S$278 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Sat, 16 Aug - Sat, 23 Aug
MDW
Chicago
YTZ
Toronto
S$278 Return, found 6 days ago
S$278
Return
found 6 days ago
Select Porter Airlines flight, departing Sat, 16 Aug from Chicago to Toronto, returning Sat, 23 Aug, priced at S$278 found 6 days ago
Porter Airlines
Thu, 28 Aug - Thu, 4 Sep
MDW
Chicago
YTZ
Toronto
S$303 Return, found 4 days ago
S$303
Return
found 4 days ago
Select Porter Airlines flight, departing Thu, 28 Aug from Chicago to Toronto, returning Thu, 4 Sep, priced at S$303 found 4 days ago
Porter Airlines
Fri, 22 Aug - Mon, 25 Aug
MDW
Chicago
YTZ
Toronto
S$343 Return, found 4 days ago
S$343
Return
found 4 days ago
Select Porter Airlines flight, departing Fri, 22 Aug from Chicago to Toronto, returning Mon, 25 Aug, priced at S$343 found 4 days ago
Porter Airlines
Thu, 4 Sep - Sun, 7 Sep
MDW
Chicago
YTZ
Toronto
S$343 Return, found 1 day ago
S$343
Return
found 1 day ago
Select Porter Airlines flight, departing Thu, 4 Sep from Chicago to Toronto, returning Sun, 7 Sep, priced at S$343 found 1 day ago
Porter Airlines
Tue, 29 Jul - Sat, 2 Aug
MDW
Chicago
YTZ
Toronto
S$374 Return, found 5 days ago
S$374
Return
found 5 days ago
Select Porter Airlines flight, departing Tue, 29 Jul from Chicago to Toronto, returning Sat, 2 Aug, priced at S$374 found 5 days ago
Porter Airlines
Fri, 29 Aug - Fri, 5 Sep
MDW
Chicago
YTZ
Toronto
S$375 Return, found 3 days ago
S$375
Return
found 3 days ago
Select Porter Airlines flight, departing Fri, 29 Aug from Chicago to Toronto, returning Fri, 5 Sep, priced at S$375 found 3 days ago
Porter Airlines
Mon, 1 Sep - Mon, 8 Sep
MDW
Chicago
YTZ
Toronto
S$375 Return, found 19 hours ago
S$375
Return
found 19 hours ago
Select Porter Airlines flight, departing Mon, 1 Sep from Chicago to Toronto, returning Mon, 8 Sep, priced at S$375 found 19 hours ago
Porter Airlines
Sun, 31 Aug - Sun, 7 Sep
MDW
Chicago
YTZ
Toronto
S$431 Return, found 1 day ago
S$431
Return
found 1 day ago
Select Porter Airlines flight, departing Sun, 31 Aug from Chicago to Toronto, returning Sun, 7 Sep, priced at S$431 found 1 day ago
Porter Airlines
Fri, 29 Aug - Fri, 5 Sep
MDW
Chicago
YTZ
Toronto
S$457 Return, found 3 days ago
S$457
Return
found 3 days ago
Select Porter Airlines flight, departing Fri, 29 Aug from Chicago to Toronto, returning Fri, 5 Sep, priced at S$457 found 3 days ago
Porter Airlines
Mon, 1 Sep - Mon, 8 Sep
MDW
Chicago
YTZ
Toronto
S$457 Return, found 19 hours ago
S$457
Return
found 19 hours ago
Select Porter Airlines flight, departing Mon, 1 Sep from Chicago to Toronto, returning Mon, 8 Sep, priced at S$457 found 19 hours ago

Find the cheapest month to fly from Chicago (MDW) to Toronto (YTZ)

November is typically the cheapest month to fly

From S$169 - S$672 per traveller.

Graph displaying average flight prices per month

Chicago to Toronto route information
Origin airport
Midway Intl.
Destination airport
Billy Bishop Toronto City
Airlines serving
Porter Airlines
Return price
S$277
Distance
707 km
Average flight time
2 hours 41 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 Porter Airlines. Our selection of flights from Midway Intl. to Billy Bishop Toronto City 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 Midway Intl. to Billy Bishop Toronto City that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$111 and roundtrip prices from S$278*.
 

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 Midway Intl. Airport (MDW) to Billy Bishop Airport?
Based on airfares listed within the last 7 days on Expedia for flights departing within the next year, round-trip flights from MDW to Billy Bishop Toronto City Airport (YTZ) start from S$278. Make your booking ASAP to secure the best price for your next big adventure. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Midway Airport to YTZ?
Each air carrier has its own set of terms and conditions. If you do decide to cancel, follow the easy instructions on our Customer Service Portal.
How do I find cheap flights from Midway Intl. Airport (MDW) to Billy Bishop Airport 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 MDW to YTZ flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ)?
With a flight distance of 710 kilometres, it's just a short hop from Midway Intl. Airport (MDW) to Billy Bishop Airport. It might be a quick one, but it's still worth bringing something to keep you busy on board.
Which airlines fly direct from Chicago Airport to Billy Bishop Airport?
Porter Airlines (PD) will get you from MDW to Billy Bishop Toronto City Airport (YTZ) safely and reliably. Choose from 82 flights every month along this route.
Are Chicago Airport to Billy Bishop Toronto City Airport (YTZ) flight tickets cheaper when they're purchased at the last minute?
Last-minute planners can sometimes nab a bargain, with some of the cheapest airfares from Chicago Airport to YTZ surfacing a few weeks before the date of departure. If you'd rather book ahead, Expedia compares and updates the best flight deals continuously — as early as a year in advance in some cases. It does depend on the carrier though, as not every airline advertises prices that far in advance.

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