Cheap flights from Chicago Midway to Toronto

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Flight deals from Chicago Midway to Toronto

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Find the cheapest month to fly from Chicago Midway to Toronto

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Toronto flights are currently cheapest in May.

Direct flights from Chicago Midway to Toronto

Alternative Chicago Midway to Toronto routes

Looking for the cheapest, fastest or easiest route from Chicago Midway to Toronto? You could fly into the following airports instead.

Chicago to Toronto: Flight information

The things to know before you go.
Cheapest flight foundC$343
Cheapest month to flyMay
Average flight time1 hr, 45 mins
Most popular airlinePorter Airlines (Canada) Ltd
Average flights per week34

Finding cheap flights from Chicago Midway to Toronto: Frequently asked questions

There are 4 airports in Toronto: Toronto Island, Toronto Pearson International, Hamilton, and Kitchener / Waterloo.
The best price we found for a round-trip flight from Chicago Midway to Toronto is C$343. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
1 hour and 45 minutes is the average flight time from Chicago Midway to Toronto.
Porter Airlines (Canada) Ltd, Porter Airlines Inc and flyGTA Airlines fly direct from Chicago Midway to Toronto.
There are 34 flights per week flying from Chicago Midway to Toronto, as of April 2024.
The cheapest month to fly from Chicago Midway to Toronto is usually May.
If you're flying from Chicago Midway Airport, the cheapest airport near Toronto is Toronto Island – which is 3.0 km away from the center of Toronto. We've found flights to this airport from C$343.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Toronto on Monday, May 27, 2024.
Yes – the average flight time is 1 hour and 45 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Toronto but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Toronto is around 40 days in advance, so don’t leave your flight to the last minute.
In April, the average temperature is usually around 6°C. July is typically the warmest month in Toronto, when it usually averages around 25°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -8°C. The rainiest month is September.
Currently, Porter Airlines (Canada) Ltd offers the cheapest flight tickets to Toronto.

Airlines that Fly from Chicago Midway Airport to Toronto

Once you have taken in all of Chicago’s infamous outdoor public art, from Picasso to Chagall, eaten your way through a Chicago-style hot dog and a deep-dish pizza or two, you are ready to leave behind the best sports city in the United States for Canada’s metropolis city of Toronto. Flying out of the second-largest airport in the state of Illinois, Chicago Midway International Airport, you are within two hours from Ontario’s capital city. Direct flights are available via flight offerings from Porter Airlines, which will take you to Toronto Island, or Delta Air, which will land you at Toronto Lester B. Pearson International Airport. Save when scheduling this getaway by utilizing Skyscanner's cheapest month search. This tool is perfect for finding cheap flights when flexibility with dates are an option. Simply select airport codes MDW to Toronto (YVR or YTC) to begin your search, keeping in mind that the weather in Chicago will likely mimic Toronto’s four distinct seasons.

Chicago Midway International Airport (MDW)

Located just thirteen kilometres from The Loop, Chicago’s central business district, lies the sprawling Chicago Midway International Airport. It can be easily accessed via the Orange Line on the rapid transit system, or L train. Home to Southwest Airlines, MDW houses forty-three aircraft gates on three concourses, and transports over twenty-two million passengers annually. Despite the magnitude of this space, MDW offers a tranquil travelling experience in the process. Within Concourse C in the Main Terminal, relax and unwind in the Yoga Room; the USO Room is a comforting space for active military personnel; the Mother’s Room in Concourse C provides a private space for nursing and parental care.

Landing in Toronto:

Landing on Toronto Island offers a unique travel itinerary, as your next steps are decided for you. A quick and pleasant ferry ride is required to get into the heart of Toronto from the island, where you will begin your cityscape adventure. If you have descended after a flight from Delta into the Toronto International Airport, you can now navigate out of Toronto’s expansive transit centre, YYZ, with every method of transportation available; quite literally planes, trains, and automobiles, are available at your every turn. Embarking upon a GO train or bus is the most cost-efficient form of transit, or an airport shuttle to transport you south to the city. Uber does not have access to this airport as of 2017, so taxicabs with set airport fares are your quickest option. Once outside YYZ is when travelling like a local is easiest; utilizing Toronto’s straightforward subway system, the Toronto Transit Commission (TTC) will save money and time avoiding traffic. However, If you would prefer to drive yourself, dive into Skyscanner’s car-rental tool and navigate this exciting city yourself.

What to Do in Toronto

Whether you are in Toronto for business or leisure, there are many exciting attractions to enjoy between meetings or to fill your days. The TTC or Go Transit can whisk you up to Vaughn for thrill-seekers wishing to get an adrenaline rush from Canada’s Wonderland’s extensive rollercoasters. Enjoy the city’s great theatres, large and small, from Factory Theatre’s cozy space to the grandeur of the Royal Alexandra Theatre. After a night at the opera, or laughing heartily at Second City, indulge in relaxing accommodations, easily and thriftily found on Skyscanner’s hotel search. Upon waking refreshed, head straight into the heart of Queen Street’s unique boutiques, tourist attractions such as the CN Tower, hipster neighborhoods nestled in Kensington Market, and an endless array of world-renowned eateries.

Attractions in Toronto:

  • Toronto Zoo
  • CN Tower
  • Ripey’s Aquarium
  • Ferry to Toronto Island
  • Concerts at Massey Hall
  • Ed Mirvish Theatre
  • Canada’s Wonderland
  • Toronto International Film Festival in early September

More flight options

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.