$89 Cheap Flights from Chicago (MDW) to Toronto (YYZ)

View $89 flight on Sat, Nov 8, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Toronto Pearson Intl. Airport (YYZ)

Cheap Flights from Chicago to Toronto (MDW-YYZ)

Prices were available within the past 7 days and start at $89 for one-way flights and $234 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Sep 2 - Sat, Sep 6
MDW
Chicago
YYZ
Toronto
$234 Roundtrip, found 3 days ago
$234
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Sep 2 from Chicago to Toronto, returning Sat, Sep 6, priced at $234 found 3 days ago
Delta
Wed, Sep 10 - Sat, Sep 13
MDW
Chicago
YYZ
Toronto
$244 Roundtrip, found 1 hour ago
$244
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Sep 10 from Chicago to Toronto, returning Sat, Sep 13, priced at $244 found 1 hour ago
Delta
Tue, Sep 2 - Sat, Sep 6
MDW
Chicago
YYZ
Toronto
$251 Roundtrip, found 3 days ago
$251
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Sep 2 from Chicago to Toronto, returning Sat, Sep 6, priced at $251 found 3 days ago
Delta
Sun, Aug 10 - Tue, Aug 19
MDW
Chicago
YYZ
Toronto
$256 Roundtrip, found 6 days ago
$256
Roundtrip
found 6 days ago
Select Delta flight, departing Sun, Aug 10 from Chicago to Toronto, returning Tue, Aug 19, priced at $256 found 6 days ago
Delta
Sat, Jul 26 - Wed, Aug 6
MDW
Chicago
YYZ
Toronto
$261 Roundtrip, found 5 days ago
$261
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jul 26 from Chicago to Toronto, returning Wed, Aug 6, priced at $261 found 5 days ago
Delta
Thu, Oct 9 - Sat, Oct 11
MDW
Chicago
YYZ
Toronto
$262 Roundtrip, just found
$262
Roundtrip
just found
Select Delta flight, departing Thu, Oct 9 from Chicago to Toronto, returning Sat, Oct 11, priced at $262 just found
Delta
Wed, Sep 10 - Mon, Sep 15
MDW
Chicago
YYZ
Toronto
$262 Roundtrip, found 11 hours ago
$262
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Sep 10 from Chicago to Toronto, returning Mon, Sep 15, priced at $262 found 11 hours ago
Delta
Tue, Aug 12 - Sun, Aug 17
MDW
Chicago
YYZ
Toronto
$264 Roundtrip, found 6 days ago
$264
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Aug 12 from Chicago to Toronto, returning Sun, Aug 17, priced at $264 found 6 days ago
Delta
Thu, Aug 21 - Sat, Aug 23
MDW
Chicago
YYZ
Toronto
$276 Roundtrip, found 4 days ago
$276
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Aug 21 from Chicago to Toronto, returning Sat, Aug 23, priced at $276 found 4 days ago
WestJet
Tue, Aug 12 - Fri, Aug 15
MDW
Chicago
YYZ
Toronto
$287 Roundtrip, found 1 hour ago
$287
Roundtrip
found 1 hour ago
Select WestJet flight, departing Tue, Aug 12 from Chicago to Toronto, returning Fri, Aug 15, priced at $287 found 1 hour ago

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

June is typically the cheapest month to fly

From $233 - $499 per traveler.

Graph displaying average flight prices per month

Alternative airports near Toronto

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

Select flight to Billy Bishop Toronto City YTZ. Cheapest and Closest option available. Average driving time to city center is 4 minutes. Flights from $311
YTZ
Billy Bishop Toronto City
CheapestClosest
Average driving time to city center4 min
Flights from $311
Flights from Chicago (MDW) to Toronto (YYZ)
Origin airport
Midway Intl.
Destination airport
Pearson Intl.
Airlines serving
Delta, WestJet
Roundtrip price
$233
Distance
432 mi

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 September. 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 $89 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 Pearson Intl. Airport (YYZ) cost?
Discover the latest flight deals from MDW to YYZ by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to YYZ?
The cheapest flights from MDW to YYZ 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 Pearson Intl. Airport (YYZ)?
While Chicago, IL (MDW-Midway Intl.) doesn't have any direct flights to Pearson Intl. Airport (YYZ), other airports have nonstop routes. Leaving from O'Hare Intl. Airport (ORD) will get you to Toronto without any detours.
What is the cheapest airline that flies from MDW to YYZ?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to YYZ. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Pearson Intl. Airport (YYZ)?
Direct flights from Midway Intl. Airport (MDW) to Pearson Intl. Airport (YYZ) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel details and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to YYZ?
Typically you'll find the largest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can change depending on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Pearson Intl. Airport (YYZ)?
To avoid potential delays on the Midway Intl. Airport (MDW) to Pearson Intl. Airport (YYZ) route, fly before 3 PM. Flights after this time are 22% more likely to be canceled.**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 touch down at Billy Bishop Toronto City Airport (YTZ) or Buffalo Niagara Intl. Airport (BUF) when you travel 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 Pearson Intl. Airport (YYZ) last-minute?
Waiting until just before your trip to book a ticket from MDW to YYZ generally means paying more. While you may come across some last-minute discounts, there's no guarantee. Keep your travel schedule open to maximize your chances of getting a bargain.
Is it cheaper to book a MDW to YYZ flight and hotel package?
You'll generally save money by securing a MDW to YYZ flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one convenient place. After choosing your preferred accommodations and flights, consider adding extras including activities, car rentals and tours.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Pearson Intl. Airport (YYZ)?
In most instances, you're able to cancel or reschedule your MDW to YYZ flight. However, there may be additional charges, especially if you made your booking more than 24 hours ago. Double-check your itinerary for the airline's fees and policies on flight changes, or if you need further information, head to our Customer Service portal.

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*Available to One Key members.