฿5,755 Cheap Flights from Toronto (YTZ) to Chicago (MDW)

View ฿5,755 flight on Tue, 2 Dec 2025Opens 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 (YTZ) to Chicago (MDW)

Prices were available within the past 7 days and start at ฿5,755 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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

September is typically the cheapest month to fly

From ฿4,740 - ฿13,351 per traveller.
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Flight from Toronto to Chicago route information
Origin airport
Billy Bishop Toronto City
Destination airport
Midway Intl.
Distance
707 km

Perfect flights from Toronto to Chicago

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Toronto to Chicago. 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 , 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 Billy Bishop Toronto City to Midway Intl. ticket options cater to your travel preferences, with incredible one-way fares from ฿5,755 and roundtrip prices . 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 Midway Intl. and explore 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 to travel arrangements today and embark on the journey of a lifetime in Chicago.

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 . 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.

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