Cheap Flights from Toronto Pearson International to Chicago Midway

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Compare Toronto Pearson International to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Toronto Pearson International to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Toronto Pearson International to Chicago Midway? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Toronto Pearson International to Chicago Midway

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

Toronto Pearson International to Chicago Midway: Alternative routes

Compare routes from Toronto Pearson International to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Toronto to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs43,742
Cheapest month to flyJune

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

The best price we found for a return flight from Toronto Pearson International to Chicago Midway is Rs69,438. 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.
Currently, there are no airlines that fly direct from Toronto Pearson International to Chicago Midway. But we found flights with one or more stops from Rs69,438.
As of March 2025, there are no flights flying from Toronto Pearson International to Chicago Midway.
The cheapest month to fly from Toronto Pearson International to Chicago Midway is usually March 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Toronto Pearson International Airport to Chicago Midway Airport on Saturday, 19 April 2025.
No airlines currently offer direct flights between Toronto Pearson International Airport and Chicago Midway Airport. Most routes have one or more stops.
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 Chicago Midway 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Delta offers the cheapest flight tickets to Chicago Midway.

How to find the cheapest flights from Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW)

  • The best price we've found for a one-way ticket from Pearson International Airport to Chicago Midway International Airport is Rs43,742. The cheapest price for a return flight is Rs69,438. Bear in mind that fares could change due to availability when booking.

  • It's a good idea to book in advance if you're hoping to get cheap flights from YYZ to MDW. That's because airlines adjust prices based on demand, which tends to increase closer to departure.

  • Finding cheap flights from Pearson International Airport to Chicago Midway International Airport is easy if you can be flexible with your travel dates. Try using the 'Whole month' search function to see the lowest fares across the month and snap up a great deal.

  • Create a Price Alert for cheap flights from YYZ to MDW. There's no need to search every day to find out if prices have fallen. We'll update you as soon as there's a change in price.

  • Use filters to tailor your flights from Pearson International Airport to Chicago Midway International Airport. Simply enter your ideal arrival and departure times, airlines and number of stops. Alternatively, sort your results by 'Cheapest' to see the best deals.

Handy information about Pearson International Airport (YYZ)

  • Pearson International Airport is around 27 kilometres from central Toronto. If you're catching a cab, ride-sharing or driving from the centre, it'll take 26 minutes or so to get there, depending on the traffic. If you're planning to take public transport, expect the trip time to be approximately 49 minutes.

  • Want an easy way to start to your break? Stay near YYZ. Whether you're on an early flight from Pearson International Airport to Chicago Midway International Airport or just don't want to be rushed, these stays have you covered:

Arriving at Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • Chicago Midway International Airport is approximately 19 kilometres from the centre of Chicago. With your own car rental or in a cab, the drive is about 21 minutes.

  • It typically takes 46 minutes if you're travelling on public transport.

When to fly to Chicago Midway International Airport (MDW)

  • It's time to pick your travel dates for your flight from Pearson International Airport to Chicago Midway International Airport. July is the busiest month to visit Chicago. If you prefer a more low-key vibe, go in May.

  • Book your flight from Pearson International Airport to Chicago Midway International Airport for July if you want to explore Chicago during its warmest month. Expect temperatures of between 15ºC and 29ºC.

  • January sees average temperatures of between -12ºC and 3ºC. Look for cheap flights from YYZ to MDW sometime around then if you want to travel when it's cooler.

More about Chicago

Complete your Chicago trip with hotels and a car rental

  • You've booked your cheap ticket to Chicago Midway International Airport — now it's time to find a place to stay, and maybe even a set of wheels. We've compared prices across hundreds of companies to bring you the best hotels and car rental deals in Chicago.

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