€137 Cheap Flights Chicago to Toronto (MDW-YTZ)

View €137 flight on Thu, 16 Oct 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 €137 for one-way flights and €295 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Transat
Thu, 9 Oct - Sun, 12 Oct
MDW
Chicago
YTZ
Toronto
€295 Return, found 5 days ago
€295
Return
found 5 days ago
Select Air Transat flight, departing Thu, 9 Oct from Chicago to Toronto, returning Sun, 12 Oct, priced at €295 found 5 days ago
Porter Airlines
Thu, 16 Oct - Sun, 19 Oct
MDW
Chicago
YTZ
Toronto
€310 Return, just found
€310
Return
just found
Select Porter Airlines flight, departing Thu, 16 Oct from Chicago to Toronto, returning Sun, 19 Oct, priced at €310 just found
Air Transat
Thu, 16 Oct - Sun, 19 Oct
MDW
Chicago
YTZ
Toronto
€311 Return, just found
€311
Return
just found
Select Air Transat flight, departing Thu, 16 Oct from Chicago to Toronto, returning Sun, 19 Oct, priced at €311 just found
Air Transat
Thu, 9 Oct - Sun, 12 Oct
MDW
Chicago
YTZ
Toronto
€317 Return, found 5 days ago
€317
Return
found 5 days ago
Select Air Transat flight, departing Thu, 9 Oct from Chicago to Toronto, returning Sun, 12 Oct, priced at €317 found 5 days ago
Air Transat
Mon, 22 Dec - Sat, 27 Dec
MDW
Chicago
YTZ
Toronto
€322 Return, found 5 days ago
€322
Return
found 5 days ago
Select Air Transat flight, departing Mon, 22 Dec from Chicago to Toronto, returning Sat, 27 Dec, priced at €322 found 5 days ago
Porter Airlines
Mon, 22 Dec - Sat, 27 Dec
MDW
Chicago
YTZ
Toronto
€322 Return, found 5 days ago
€322
Return
found 5 days ago
Select Porter Airlines flight, departing Mon, 22 Dec from Chicago to Toronto, returning Sat, 27 Dec, priced at €322 found 5 days ago
Porter Airlines
Thu, 16 Oct - Sun, 19 Oct
MDW
Chicago
YTZ
Toronto
€325 Return, just found
€325
Return
just found
Select Porter Airlines flight, departing Thu, 16 Oct from Chicago to Toronto, returning Sun, 19 Oct, priced at €325 just found
Air Transat
Thu, 9 Oct - Sun, 12 Oct
MDW
Chicago
YTZ
Toronto
€325 Return, found 5 days ago
€325
Return
found 5 days ago
Select Air Transat flight, departing Thu, 9 Oct from Chicago to Toronto, returning Sun, 12 Oct, priced at €325 found 5 days ago
Air Transat
Thu, 16 Oct - Sun, 19 Oct
MDW
Chicago
YTZ
Toronto
€330 Return, just found
€330
Return
just found
Select Air Transat flight, departing Thu, 16 Oct from Chicago to Toronto, returning Sun, 19 Oct, priced at €330 just found
Air Transat
Sat, 11 Oct - Sun, 12 Oct
MDW
Chicago
YTZ
Toronto
€340 Return, found 2 days ago
€340
Return
found 2 days ago
Select Air Transat flight, departing Sat, 11 Oct from Chicago to Toronto, returning Sun, 12 Oct, priced at €340 found 2 days ago

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

November is typically the cheapest month to fly

From €122 - €434 per traveller.
Chicago to Toronto route information
Origin airport
Midway Intl.
Destination airport
Billy Bishop Toronto City
Airlines serving
Air Transat, Porter Airlines
Return price
€295
Distance
707 km
Average flight time
2 hours 42 mins

Perfect flights from Chicago to Toronto

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Chicago to Toronto. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of Toronto, surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible Midway Intl. to Billy Bishop Toronto City ticket options cater to your travel preferences, with incredible one-way fares from €137 and roundtrip prices from €295. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Billy Bishop Toronto City and explore Toronto and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your MDW to YTZ travel arrangements today and embark on the journey of a lifetime in Toronto.

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 €295. 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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