€95 Cheap Flights Toronto to Chicago (YTZ-MDW)

View €95 flight on Thu, 5 Mar 2026Opens in a new window

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

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Cheap flights from Toronto to Chicago (YTZ-MDW)

Prices were available within the past 7 days and start at €95 for one-way flights and €152 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Transat
Thu, 5 Mar - Wed, 11 Mar
YTZ
Toronto
MDW
Chicago
€152 Return, found 2 hours ago
€152
Return
found 2 hours ago
Select Air Transat flight, departing Thu, 5 Mar from Toronto to Chicago, returning Wed, 11 Mar, priced at €152 found 2 hours ago
Air Transat
Mon, 12 Jan - Mon, 19 Jan
YTZ
Toronto
MDW
Chicago
€153 Return, found 5 days ago
€153
Return
found 5 days ago
Select Air Transat flight, departing Mon, 12 Jan from Toronto to Chicago, returning Mon, 19 Jan, priced at €153 found 5 days ago
Porter Airlines
Thu, 5 Mar - Wed, 11 Mar
YTZ
Toronto
MDW
Chicago
€158 Return, found 2 hours ago
€158
Return
found 2 hours ago
Select Porter Airlines flight, departing Thu, 5 Mar from Toronto to Chicago, returning Wed, 11 Mar, priced at €158 found 2 hours ago
Porter Airlines
Mon, 12 Jan - Mon, 19 Jan
YTZ
Toronto
MDW
Chicago
€159 Return, found 5 days ago
€159
Return
found 5 days ago
Select Porter Airlines flight, departing Mon, 12 Jan from Toronto to Chicago, returning Mon, 19 Jan, priced at €159 found 5 days ago
Air Transat
Thu, 5 Mar - Wed, 11 Mar
YTZ
Toronto
MDW
Chicago
€165 Return, found 2 hours ago
€165
Return
found 2 hours ago
Select Air Transat flight, departing Thu, 5 Mar from Toronto to Chicago, returning Wed, 11 Mar, priced at €165 found 2 hours ago
Porter Airlines
Thu, 5 Mar - Wed, 11 Mar
YTZ
Toronto
MDW
Chicago
€165 Return, found 2 hours ago
€165
Return
found 2 hours ago
Select Porter Airlines flight, departing Thu, 5 Mar from Toronto to Chicago, returning Wed, 11 Mar, priced at €165 found 2 hours ago
Air Transat
Sat, 15 Nov - Sun, 16 Nov
YTZ
Toronto
MDW
Chicago
€234 Return, found 14 hours ago
€234
Return
found 14 hours ago
Select Air Transat flight, departing Sat, 15 Nov from Toronto to Chicago, returning Sun, 16 Nov, priced at €234 found 14 hours ago
Porter Airlines
Sat, 15 Nov - Sun, 16 Nov
YTZ
Toronto
MDW
Chicago
€239 Return, found 14 hours ago
€239
Return
found 14 hours ago
Select Porter Airlines flight, departing Sat, 15 Nov from Toronto to Chicago, returning Sun, 16 Nov, priced at €239 found 14 hours ago
Air Transat
Thu, 4 Dec - Mon, 8 Dec
YTZ
Toronto
MDW
Chicago
€247 Return, found 1 day ago
€247
Return
found 1 day ago
Select Air Transat flight, departing Thu, 4 Dec from Toronto to Chicago, returning Mon, 8 Dec, priced at €247 found 1 day ago
Porter Airlines
Thu, 4 Dec - Mon, 8 Dec
YTZ
Toronto
MDW
Chicago
€251 Return, found 1 day ago
€251
Return
found 1 day ago
Select Porter Airlines flight, departing Thu, 4 Dec from Toronto to Chicago, returning Mon, 8 Dec, priced at €251 found 1 day ago

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

September is typically the cheapest month to fly

From €124 - €351 per traveller.

Frequently asked questions

How much is a flight from Billy Bishop Toronto City Airport (YTZ) to Chicago Airport?
Based on airfares available within the last 7 days on Expedia for flights departing within the next year, round-trip journeys between Billy Bishop Airport and Midway Airport start from €152. Make your booking today to score the best price for your 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 YTZ to MDW?
The majority of flights can be cancelled online, but each airline has its own set of terms and conditions. If you do decide to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from YTZ to Chicago 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 Billy Bishop Airport to MDW flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Billy Bishop Airport to Midway Airport?
That new movie you've been desperate to see will just have to wait — the flight distance between Billy Bishop Toronto City Airport (YTZ) (YTZ) and Midway Intl. Airport (MDW) (MDW) is only 710 kilometres. The captain will be telling you to put your seat upright for touchdown before you know it.
Which airlines fly direct from Billy Bishop Toronto City Airport (YTZ) to Midway Airport?
If you'd like to fly directly from YTZ to MDW, Porter Airlines (PD) is a popular option. It operates 82 flights each month between Toronto and Chicago.
Are Billy Bishop Airport to Chicago Airport flight tickets cheaper when they're purchased at the last minute?
Flight prices go up and down like a yo-yo, so not always. While last-minute deals between YTZ and Chicago Airport are of course possible, it's also a good idea to keep a close eye on prices well before you fly. In fact, some carriers release their prices up to a year before the departure date. Expedia is constantly updating the biggest airfare bargains around, so keep checking back and be ready to grab your seat when the price is right.

Travel information

0
Origin airport
Billy Bishop Toronto City
Destination airport
Midway Intl.
Airlines serving
Air Transat, Porter Airlines
Return price
€151
Distance
707 km

Book with confidence

Perfect flights from Toronto to Chicago

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Our flexible Billy Bishop Toronto City to Midway Intl. ticket options cater to your travel preferences, with incredible one-way fares from €95 and roundtrip prices from €152. 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.
 
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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 to travel arrangements today and embark on the journey of a lifetime in Chicago.
Perfect flights from Toronto to Chicago

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