The cheapest times to fly from YTZ to MDW are

  • January 1st to February 18th
  • July 30th to December 16th (except the week of October 1st)

based on data collected exclusively by Champion Traveler across tens of millions of flights. Among all the dates above, the very cheapest time to fly from YTZ to MDW is late October. Prices can be as high as $349 for Sunday flights during early to mid July, or as low as $246 for Wednesday flights around late October.


When to Fly to Chicago

Flying from Toronto (YTZ) to Chicago, IL (MDW) will usually cost between $252 to $313 per person if booking more than four weeks in advance. On average the very cheapest time to fly is late October with an average ticket price of $246. Due to high demand the most expensive time to fly is early to mid July, with an average price of $300. Planning your trip to low-cost times can easily save you $54 on economy flights and even more on first-class flights. Generally, any price below $279 can be considered a good price for a round-trip YTZ to MDW flight.

See below for a graph of average weekly prices for the YTZ to MDW route. All prices are for round-trip tickets in USD.

YTZ to MDW Flight Prices

Compared to other flights, the YTZ to MDW flight is much cheaper than the average and costs much less than the average flight leaving from Toronto. The average price per mile (for a direct flight) is $0.39, which is a bit above average.


Flight Prices by Day of the Week

Wednesday is usually the cheapest day to depart and return on this flight. Sundays are the most expensive days to fly out or take a return trip. Selecting flights on the least expensive days could save you up to $8 (3%) on this flight.

Departing prices are for round-trip flights returning on the day of departure. For example, a flight departing on Wednesday and returning a week later will cost an average of $272. Return trip prices are from the MDW to YTZ flight, and often highlight the quality of our data in showing the same trend.

Departing Prices by Day

Departure Day Prices

Return Trip Prices by Day

Return Day Prices


Nonstop Flights and Layovers

Travelers looking to fly from YTZ to MDW can generally find a 0-layover flight. Because there is a direct flight option the real-world direct flight time of 1 hour 47 minutes may be realistic.


Flight Questions Answered

Still have questions about flying from YTZ to MDW? We’ve got answers.

Which airlines fly this route?

You can find 1 major airline flying this route most often: Porter Airlines, and potentially more during busy seasons.

How far away is it from Chicago Midway International Airport to Billy Bishop Toronto City Airport?

The distance between the two airports is roughly 443 miles or 713 kilometers.

How long does it take to fly from YTZ to MDW?

The real-world flight time for a nonstop YTZ to MDW flight is about 1 hour 47 minutes.

How many flights go between Toronto and Chicago, IL?

It depends on the day of the week and the date, but a typical day might have around 6 available flights from YTZ to MDW.


Airport Location Info


Departing Airport

Origination code YTZ
Origination airport name Billy Bishop Toronto City Airport
City Toronto
Country Canada
Latitude 43.6
Longitude -79.4

Return Airport

Destination code MDW
Destination airport name Chicago Midway International Airport
City Chicago, IL
Country the United States
Latitude 41.8
Longitude -87.8


Other Resources

Please note that while we’ve worked hard to analyzed tens of millions of flights to get you this data, we do not calculate current live prices or guarantee pricing. Please see our partners using the links above for current offers.