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Cheap Flights from Toronto to Chicago $213.04

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Cheapest Flights from Toronto to Chicago (YYZ to MDW)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Toronto to Chicago (YYZ to MDW)

Question : Should you take that vacation to Chicago in the next 30 days?
Answer : Feb 21st has seen bookings (as of Feb 20th) as cheap as $250. That comes in 29% below the average price for this route. Saving now means you'll have more money to spend on your trip.

Question : Are you paying the cheapest or highest price for your ticket to Chicago?
Answer : Flight prices fluctuate more than the majority of routes from Canada for YYZ to MDW. They range from $250 to $503. Prices tend to be lower the further out you book.

Question : Is Pearson International Airport (YYZ) the cheapest airport for getting to Chicago Midway International Airport (MDW)?
Answer : Departing from Pearson International Airport is not the only way to get to Chicago Midway International Airport. Try looking for flights from Toronto City Centre Airport (YTZ) as well. Over the upcoming months, flights from YTZ to MDW are being booked 41% cheaper than flights from YYZ to MDW. Being only 11 miles away, it's easily accessible for most.

Question : Over the coming months, which airline is getting their passengers to Chicago Midway International Airport (MDW) round-trip the cheapest?
Answer : Prices are hitting as high as $503 over the next three months when flying to MDW from YYZ. Check out Delta Air Lines, as they have been booking customers at just $250.

Question : Is there a preferred airline for getting to Chicago Midway International Airport (MDW) on time?
Answer : Air Canada holds the best record for flights from YYZ to MDW with a 100% on-time rate. Hopefully they keep that perfect record alive.

Question : How many days should you spend in Chicago?
Answer : Over the next two months, passengers from YYZ to MDW are planning on staying for 10 days on average.

Question : Will you do what it takes to get the absolute cheapest flight?
Answer : The lowest-cost day to fly in March is Tuesday. Having flexibility in your travel plans means you can save more, so be sure to plan ahead when possible.

Question : Who struggles with getting their passengers to Chicago Midway International Airport (MDW) on time?
Answer : If you decide to book your flight with NetJets Aviation, keep an eye on your departure time. 100% of flights from Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW) are delayed.

Question : How often are flights late from Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW)?
Answer : This particular route gets passengers to Chicago Midway International Airport on time 30% of the time, which puts it in the bottom 25% of the world. If a flight is delayed, expect an average of less than half an hour added to your flight time.

Question : How does Toronto to Chicago stack up against the rest of the world in overall promptness?
Answer : YYZ to MDW currently scores 1 out of a possible 5 stars in promptness. This score combines both the number of delayed flights and total delay minutes. With 1 star, you should feel rather worried about getting to Chicago on time.