$63 Cheap Flights from Chicago (MDW) to Toronto (YTZ)

View $63 flight on Tue, Dec 2, 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 $63 for one-way flights and $176 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Tue, Aug 26 - Sat, Sep 6
MDW
Chicago
YTZ
Toronto
$176 Roundtrip, found 5 days ago
$176
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Tue, Aug 26 from Chicago to Toronto, returning Sat, Sep 6, priced at $176 found 5 days ago
Porter Airlines
Tue, Jul 29 - Mon, Aug 11
MDW
Chicago
YTZ
Toronto
$183 Roundtrip, found 2 days ago
$183
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Tue, Jul 29 from Chicago to Toronto, returning Mon, Aug 11, priced at $183 found 2 days ago
Porter Airlines
Wed, Sep 10 - Fri, Sep 12
MDW
Chicago
YTZ
Toronto
$187 Roundtrip, found 2 days ago
$187
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Wed, Sep 10 from Chicago to Toronto, returning Fri, Sep 12, priced at $187 found 2 days ago
Air Transat
Mon, Sep 15 - Mon, Sep 22
MDW
Chicago
YTZ
Toronto
$189 Roundtrip, found 6 days ago
$189
Roundtrip
found 6 days ago
Select Air Transat flight, departing Mon, Sep 15 from Chicago to Toronto, returning Mon, Sep 22, priced at $189 found 6 days ago
Air Transat
Fri, Jul 18 - Thu, Oct 23
MDW
Chicago
YTZ
Toronto
$196 Roundtrip, found 2 days ago
$196
Roundtrip
found 2 days ago
Select Air Transat flight, departing Fri, Jul 18 from Chicago to Toronto, returning Thu, Oct 23, priced at $196 found 2 days ago
Porter Airlines
Tue, Jul 22 - Fri, Jul 25
MDW
Chicago
YTZ
Toronto
$200 Roundtrip, found 2 days ago
$200
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Tue, Jul 22 from Chicago to Toronto, returning Fri, Jul 25, priced at $200 found 2 days ago
Porter Airlines
Thu, Aug 7 - Mon, Aug 11
MDW
Chicago
YTZ
Toronto
$200 Roundtrip, found 4 days ago
$200
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Thu, Aug 7 from Chicago to Toronto, returning Mon, Aug 11, priced at $200 found 4 days ago
Air Transat
Fri, Jul 18 - Fri, Jul 25
MDW
Chicago
YTZ
Toronto
$201 Roundtrip, found 2 days ago
$201
Roundtrip
found 2 days ago
Select Air Transat flight, departing Fri, Jul 18 from Chicago to Toronto, returning Fri, Jul 25, priced at $201 found 2 days ago
Porter Airlines
Sat, Aug 30 - Wed, Sep 3
MDW
Chicago
YTZ
Toronto
$203 Roundtrip, found 5 days ago
$203
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Sat, Aug 30 from Chicago to Toronto, returning Wed, Sep 3, priced at $203 found 5 days ago
Porter Airlines
Fri, Aug 22 - Sun, Aug 31
MDW
Chicago
YTZ
Toronto
$210 Roundtrip, found 5 days ago
$210
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Fri, Aug 22 from Chicago to Toronto, returning Sun, Aug 31, priced at $210 found 5 days ago

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

November is typically the cheapest month to fly

From $132 - $523 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (MDW) to Toronto (YTZ)
Origin airport
Midway Intl.
Destination airport
Billy Bishop Toronto City
Airlines serving
Air Transat, Porter Airlines
Roundtrip price
$176
Distance
442 mi
Average flight time
2 hours 41 mins

Chicago to Toronto Flights

The cheapest times to fly from Chicago to Toronto

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Toronto are during the month of August. You can find some of the cheapest flights from Chicago to Toronto with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Toronto

Sunday is one of the best days to book for cheap flights from Chicago to Toronto: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Toronto

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Toronto in 2025. You can also book with separate airlines for your outbound and return journeys, from $63 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Toronto flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Toronto airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ) cost?
Score affordable return tickets from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ) starting at $167. Grab a seat and start your adventure. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Porter Airlines and Air Canada flight leaving MDW on July 21 2025 and touching down at YTZ. The price was last updated on July 6 2025 and has not changed since.
What is the cheapest month to fly from MDW to YTZ?
The cheapest flights from MDW to YTZ are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ)?
When jetting out of Midway Intl. Airport (MDW), you can hop on a nonstop flight to Billy Bishop Toronto City Airport (YTZ) with Porter Airlines.
What is the cheapest airline that flies from MDW to YTZ?
With prices as low as $63 for a one-way flight from MDW to YTZ, Porter Airlines is currently the cheapest airline for this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on September 29 2025. Prices were last updated on July 6 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ)?
On average, you can take your pick of 6 nonstop flights departing from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ) per week. If you can't see one that works for your schedule, think about booking a flight with a layover. Filter your search results on Expedia to include one stop or more and select the next best alternative.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ)?
Flights between MDW and YTZ tend to be busiest at 1 PM. If you'd like a more relaxed trip and potentially cheaper prices, choose a time when demand is lower.
What day of the week has the most flights from MDW to YTZ?
If you travel on a Friday, you'll get the widest range of choices for flights from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ).
What is the earliest flight from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ)?
Midway Intl. Airport (MDW)'s first flight to Billy Bishop Toronto City Airport (YTZ) departs at approximately 1:05PM UTC-6. With a total journey time of 1h 42m, you'll touch down at around 3:47PM UTC-5.
How long does it take to fly from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ)?
The average flight duration from MDW to YTZ is 1 hour and 42 minutes, covering a total distance of 440 mi.
What airline has the least delays from MDW to YTZ?
Porter Airlines has the strongest track record for on-time direct flights from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ), with an on-time rating of 86%. Use the Expedia App to look up your journey status before you go and get real-time updates about any trip changes.
What is the best time to fly from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ)?
To reach Billy Bishop Toronto City Airport (YTZ) on schedule, choose a flight that takes off from Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Toronto from Midway Intl. Airport (MDW)?
You can arrive at Billy Bishop Toronto City Airport (YTZ) or Buffalo Niagara Intl. Airport (BUF) when traveling to Toronto on a direct flight from Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ) last-minute?
Last-minute fares from MDW to YTZ are usually more expensive. To secure the lowest rates, start searching for flights well in advance. That said, if you're flexible with your travel dates, you may land a cheap ticket right before you leave.
Is it cheaper to book a MDW to YTZ flight and hotel package?
You'll generally save money by booking a MDW to YTZ flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. Once you've selected your ideal flights and accommodations, you can add extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ)?
It's generally possible to cancel or reschedule your MDW to YTZ flight. However, for bookings made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find further details on our Customer Service portal.

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