$64 Cheap Flights from Chicago (MDW) to Toronto (YTZ)

View $64 flight on Fri, Mar 27, 2026Opens in a new window

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

Cheap Flights from Chicago to Toronto (MDW-YTZ)

Prices were available within the past 7 days and start at $64 for one-way flights and $171 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Thu, Jan 29 - Wed, Feb 18
MDW
Chicago
YTZ
Toronto
$171 Roundtrip, found 16 hours ago
$171
Roundtrip
found 16 hours ago
Select Porter Airlines flight, departing Thu, Jan 29 from Chicago to Toronto, returning Wed, Feb 18, priced at $171 found 16 hours ago
Air Transat
Thu, Apr 16 - Mon, Apr 20
MDW
Chicago
YTZ
Toronto
$173 Roundtrip, found 6 hours ago
$173
Roundtrip
found 6 hours ago
Select Air Transat flight, departing Thu, Apr 16 from Chicago to Toronto, returning Mon, Apr 20, priced at $173 found 6 hours ago
Air Transat
Sun, Mar 15 - Fri, Mar 20
MDW
Chicago
YTZ
Toronto
$174 Roundtrip, found 1 hour ago
$174
Roundtrip
found 1 hour ago
Select Air Transat flight, departing Sun, Mar 15 from Chicago to Toronto, returning Fri, Mar 20, priced at $174 found 1 hour ago
Air Transat
Fri, Feb 20 - Tue, Feb 24
MDW
Chicago
YTZ
Toronto
$175 Roundtrip, found 2 days ago
$175
Roundtrip
found 2 days ago
Select Air Transat flight, departing Fri, Feb 20 from Chicago to Toronto, returning Tue, Feb 24, priced at $175 found 2 days ago
Air Transat
Sun, Mar 15 - Fri, Mar 20
MDW
Chicago
YTZ
Toronto
$200 Roundtrip, found 1 hour ago
$200
Roundtrip
found 1 hour ago
Select Air Transat flight, departing Sun, Mar 15 from Chicago to Toronto, returning Fri, Mar 20, priced at $200 found 1 hour ago
Air Transat
Sun, Mar 29 - Tue, Mar 31
MDW
Chicago
YTZ
Toronto
$203 Roundtrip, found 2 days ago
$203
Roundtrip
found 2 days ago
Select Air Transat flight, departing Sun, Mar 29 from Chicago to Toronto, returning Tue, Mar 31, priced at $203 found 2 days ago
Air Transat
Sun, Mar 15 - Fri, Mar 20
MDW
Chicago
YTZ
Toronto
$204 Roundtrip, found 1 hour ago
$204
Roundtrip
found 1 hour ago
Select Air Transat flight, departing Sun, Mar 15 from Chicago to Toronto, returning Fri, Mar 20, priced at $204 found 1 hour ago
Air Transat
Fri, Feb 20 - Tue, Feb 24
MDW
Chicago
YTZ
Toronto
$206 Roundtrip, found 2 days ago
$206
Roundtrip
found 2 days ago
Select Air Transat flight, departing Fri, Feb 20 from Chicago to Toronto, returning Tue, Feb 24, priced at $206 found 2 days ago
Porter Airlines
Thu, Mar 19 - Sun, Mar 22
MDW
Chicago
YTZ
Toronto
$208 Roundtrip, found 4 days ago
$208
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Thu, Mar 19 from Chicago to Toronto, returning Sun, Mar 22, priced at $208 found 4 days ago
Porter Airlines
Wed, Mar 11 - Sun, Mar 15
MDW
Chicago
YTZ
Toronto
$208 Roundtrip, found 6 days ago
$208
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Wed, Mar 11 from Chicago to Toronto, returning Sun, Mar 15, priced at $208 found 6 days ago

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

September is typically the cheapest month to fly

From $143 - $326 per traveler.

Alternative airports near Toronto

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Pearson Intl. YYZ. Cheapest option available. Average driving time to city center is 22 minutes. Flights from $357
YYZ
Pearson Intl.
Cheapest
Average driving time to city center22 min
Flights from $357
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
$171
Distance
442 mi
Average flight time
2 hours 42 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 January. 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 $64 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?
Snag a cheap one-way flight from $64 or cheap return flight from $171 from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ)?
January is the cheapest month to fly from MDW to YTZ. Traveling during quieter months is often the key to finding better deals on flights.
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 Midway Intl. Airport (MDW) to Billy Bishop Toronto City Airport (YTZ)?
To find the cheapest airline that'll fly you from MDW to YTZ, use Expedia's filter tool. Tailor your search based on your travel style, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
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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*Available to One Key members.