YYZ to MDW (Toronto to Chicago) Flights

Last Minute Flights from YYZ to MDW

Best airfare and ticket deals for YYZ to MDW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
YYZChicagoMarch 30 to April 2$459
*Prices include taxes and fees

Cheapest YYZ to MDW Flights

Best airfare and ticket deals for YYZ to MDW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
YYZChicagoApril 24 to May 7$261
YYZChicagoJune 8 to June 29$267
YYZChicagoApril 16 to April 17$270
YYZChicagoApril 20 to April 24$315
*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

Which airlines with flights from Pearson International Airport to Midway International Airport allow free cancellation due to COVID-19?
For a list of airlines offering flexible COVID-19 related changes, make the most of our convenient filter function. Get started by typing in your dates. Then, once all the available flights are on display, check the “No change fee” box under the “Flexible change policies” subheading on the left. Read through the carrier’s cancellation rules before finalizing your Pearson International Airport to Midway International Airport ticket.
What airlines fly direct from YYZ to Chicago Airport?
No air carriers fly straight from YYZ to Chicago, IL Airport (MDW-Midway Intl.). If you’re planning a trip to Chicago, book a journey with at least one stop in between.
How many flights are there from YYZ to MDW?
Approximately 5 per day. If you’re in a big rush to fly to Chicago, see if you can get your hands on a last-minute deal from Toronto, ON Airport (YYZ-Pearson Intl.) to Chicago, IL Airport (MDW-Midway Intl.) and then reserve it straight away!
How long does it take to fly from Toronto, ON Airport (YYZ-Pearson Intl.) to Chicago, IL Airport (MDW-Midway Intl.)?
Around 3 hours and 20 minutes. Booked on a day flight? Secure a seat by a window and gaze out at the views below. Or, if you’re jetting from Toronto, ON Airport (YYZ-Pearson Intl.) to Chicago, IL Airport (MDW-Midway Intl.) in the evening, catch some z’s and land in Chicago well rested.
What is the flight distance from Toronto, ON Airport (YYZ-Pearson Intl.) to Chicago, IL Airport (MDW-Midway Intl.)?
The short-haul journey from Toronto to Chicago is a swift 430 miles (700 km). Don’t get too comfortable though — you’ll be grabbing your bags at Chicago, IL Airport (MDW-Midway Intl.) not long after taking off!
How many morning flights are there from YYZ to MDW?
Buckle up and travel from YYZ to MDW on one of the 21 morning flights each week. Delta (DL) operates 21 of these services leaving before midday. 6:10AM is the earliest departure you can book with this carrier.
How many afternoon flights are there from YYZ to MDW?
Pick one of the 20 weekly afternoon and evening flights from YYZ to MDW and catch a few more z’s. Leading carrier Delta (DL) advertises 20 of these later flights which start at 12:00PM.
What is the earliest departure time out of Toronto to Chicago?
Leave YYZ at 6:10AM and arrive at MDW at 1:47PM. This is the earliest service available on this route.
What is the latest departure time out of Toronto to Chicago?
Lock in a seat on the 4:00PM flight from YYZ, landing at 1:47PM at MDW, and give yourself time to finish up those last-minute vacation preparations. This is the latest flight you can get on this route.
What is the average price from Toronto to Chicago?
Round-trip journeys from YYZ to MDW begin from around $261. Amazing fares don’t last forever, so get set to click “book” when you spy 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 perhaps simply to treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find the cheapest flights from YYZ to MDW, we’ve got you covered here at Flights.com.

We present you with some of the hottest 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.