YYZ to MDW (Toronto to Chicago) Flights

Last Minute Flights from YYZ to MDW

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
YYZChicagoMarch 22 to March 26$575
*Prices include taxes and fees

Cheapest YYZ to MDW Flights

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
YYZChicagoApril 1 to April 7$266
YYZChicagoMay 21 to May 26$268
YYZChicagoMay 5 to May 8$271
YYZChicagoMay 15 to May 28$355
*Prices include taxes and fees
YYZ to MDW Flight Details
Origin airport
Pearson Intl.
Origin airport IATA code
YYZ
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Distance
432 mi

Frequently asked questions

What airlines fly direct from Toronto Pearson Airport to Chicago Airport?
Unfortunately, you can't fly nonstop from Toronto Pearson Airport to MDW. Travel to Chicago by locking in a flight with one or more stops in between. If you've got spare time, why not spend a couple of days in your layover destination?
How many flights are there from YYZ to MDW?
Approximately 10 each day. If you're in a rush to head to Chicago, see if you can grab an incredible last-minute deal from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.) and then reserve it quick!
How long does it take to fly from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.)?
This flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.) will take around 3 hours and 26 minutes. Use the time to begin the novel that's been sitting on your bookcase for ages or just enjoy a snooze.
What is the flight distance from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.)?
It's an easy breezy 430 miles (700 1) from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.), making it a short-haul flight. Stake out a window seat and be wowed by the aerial views of Chicago as you prepare for landing.
How many morning flights are there from YYZ to MDW?
Fasten your seat belt and journey from YYZ to MDW aboard one of the 34 morning flights each week. Delta Air Lines (DL) lists 26 of these services that take off before noon. 6:04AM is the earliest departure time available with DL.
How many afternoon flights are there from YYZ to MDW?
With 41 weekly afternoon and evening flights from YYZ to MDW, there's no need to set your alarm. Look up the deals from Delta Air Lines (DL) and you'll have your pick of 31 flights each week that leave after midday. The first departs at 12:30PM.
What is the earliest departure time out of Mississauga to Chicago?
6:04AM is the earliest scheduled flight that leaves from YYZ, landing at MDW at 6:06PM. Save precious minutes in the morning by having your suitcase zipped up and ready to be bundled into your ride.
What is the latest departure time out of Mississauga to Chicago?
From YYZ, the latest flight you can catch jets off at 9:00PM and comes in at 1:00PM at MDW. If you don't enjoy early mornings, this is the perfect flight for you.
What is the average price from Mississauga to Chicago?
Round-trip tickets from YYZ to MDW start from around $266. Amazing deals get snapped up fast, so be prepared to hit "book" when you spot a bargain. This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Toronto to Chicago Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from Toronto to Chicago to attend your cousin’s wedding, to pitch a business idea to your boss, or simply treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find our cheapest flights from YYZ to MDW, we’ve got you covered here at Flights.com.

We present you with some of the most affordable deals on airfare, so stop that Google flights search. We want you to spend less on your flight from Toronto to Chicago, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.

Plan Your Trip