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

View $89 flight on Mon, Nov 24, 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 $233 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Nov 25 - Fri, Nov 28
MDW
Chicago
YYZ
Toronto
$233 Roundtrip, found 6 hours ago
$233
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Nov 25 from Chicago to Toronto, returning Fri, Nov 28, priced at $233 found 6 hours ago
Delta
Thu, Nov 6 - Fri, Nov 7
MDW
Chicago
YYZ
Toronto
$233 Roundtrip, found 1 day ago
$233
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Nov 6 from Chicago to Toronto, returning Fri, Nov 7, priced at $233 found 1 day ago
Delta
Fri, Feb 20 - Tue, Feb 24
MDW
Chicago
YYZ
Toronto
$261 Roundtrip, found 8 hours ago
$261
Roundtrip
found 8 hours ago
Select Delta flight, departing Fri, Feb 20 from Chicago to Toronto, returning Tue, Feb 24, priced at $261 found 8 hours ago
WestJet
Tue, Nov 11 - Tue, Nov 18
MDW
Chicago
YYZ
Toronto
$278 Roundtrip, found 5 days ago
$278
Roundtrip
found 5 days ago
Select WestJet flight, departing Tue, Nov 11 from Chicago to Toronto, returning Tue, Nov 18, priced at $278 found 5 days ago
WestJet
Tue, Dec 23 - Sat, Jan 3
MDW
Chicago
YYZ
Toronto
$279 Roundtrip, found 9 hours ago
$279
Roundtrip
found 9 hours ago
Select WestJet flight, departing Tue, Dec 23 from Chicago to Toronto, returning Sat, Jan 3, priced at $279 found 9 hours ago
Delta
Thu, Dec 11 - Mon, Dec 15
MDW
Chicago
YYZ
Toronto
$287 Roundtrip, found 8 hours ago
$287
Roundtrip
found 8 hours ago
Select Delta flight, departing Thu, Dec 11 from Chicago to Toronto, returning Mon, Dec 15, priced at $287 found 8 hours ago
Delta
Sat, Jun 20 - Mon, Jun 22
MDW
Chicago
YYZ
Toronto
$298 Roundtrip, found 13 hours ago
$298
Roundtrip
found 13 hours ago
Select Delta flight, departing Sat, Jun 20 from Chicago to Toronto, returning Mon, Jun 22, priced at $298 found 13 hours ago
Delta
Wed, May 27 - Sat, May 30
MDW
Chicago
YYZ
Toronto
$300 Roundtrip, found 12 hours ago
$300
Roundtrip
found 12 hours ago
Select Delta flight, departing Wed, May 27 from Chicago to Toronto, returning Sat, May 30, priced at $300 found 12 hours ago
WestJet
Mon, Mar 30 - Wed, Apr 1
MDW
Chicago
YYZ
Toronto
$304 Roundtrip, found 9 hours ago
$304
Roundtrip
found 9 hours ago
Select WestJet flight, departing Mon, Mar 30 from Chicago to Toronto, returning Wed, Apr 1, priced at $304 found 9 hours ago
WestJet
Fri, Jun 26 - Mon, Jun 29
MDW
Chicago
YYZ
Toronto
$306 Roundtrip, found 9 hours ago
$306
Roundtrip
found 9 hours ago
Select WestJet flight, departing Fri, Jun 26 from Chicago to Toronto, returning Mon, Jun 29, priced at $306 found 9 hours 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.

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. Closest option available. Average driving time to city center is 4 minutes. Flights from $504
YTZ
Billy Bishop Toronto City
Closest
Average driving time to city center4 min
Flights from $504
Flights from Chicago (MDW) to Toronto (YYZ)
Origin airport
Midway Intl.
Destination airport
Pearson Intl.
Airlines serving
Delta, WestJet
Roundtrip price
$232
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 November. 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?
Snag a cheap one-way flight from $89 or cheap return flight from $233 from Midway Intl. Airport (MDW) to Pearson Intl. Airport (YYZ) 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 Pearson Intl. Airport (YYZ)?
Planning your trip for November may help you find better deals, as it's the cheapest month for flights between MDW and YYZ. You'll often find the lowest prices during off-peak months.
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 Midway Intl. Airport (MDW) to Pearson Intl. Airport (YYZ)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to YYZ flight.
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.