Cheap Flights from Toronto Pearson International to Chicago Midway

Compare Toronto Pearson International to Chicago Midway flight deals

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

Book the best Chicago Midway fare with no extra fees

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 October.

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 foundRs41,332
Cheapest month to flyOctober

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 Rs66,784. 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 Rs66,784.
As of September 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 October.
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 Thursday, 16 October 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, WestJet offers the cheapest flight tickets to Chicago Midway.

Flying from Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW): what you need to know

  • The timezone in Chicago is UTC-5, which is one hour behind Toronto.

  • Leave plenty of time to make your YYZ to MDW flight. It's generally best to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • You can expect bigger queues in popular months such as August. Arriving up to four hours in advance for an international flight and two hours for domestic departures will give you ample time for security and boarding.

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

  • The cheapest price we've found for a one-way Pearson International Airport to Chicago Midway International Airport flight is Rs41,332. A return ticket right now is Rs66,784. Depending on the availability and when you book, these fares could change.

  • To find cheap tickets from YYZ to MDW, book ahead. Airlines tend to offer their most competitively priced fares when flights are first released.

  • The 'Whole month' tool shows you the cheapest flights from Pearson International Airport to Chicago Midway International Airport throughout the month. It's an easy way to find a bargain if your dates aren't set in stone.

  • You won't have to check every day to find out if fares have dropped when you create a Price Alert. We'll notify you the moment there's a new deal on cheap flights from YYZ to MDW.

  • Select your preferred departure and arrival times, airlines and number of stops with the filters. Or sort your results by 'Cheapest' to find the best deals on flights from Pearson International Airport to Chicago Midway International Airport.

Handy information about Pearson International Airport (YYZ)

Arriving at Chicago Midway International Airport (MDW)

  • The last thing you want is a long trip to your hotel if you're arriving on a late Pearson International Airport to Chicago Midway International Airport flight. Check in to one of these accommodation options near MDW instead:

  • Get your adventure underway by picking up a Chicago Midway International Airport rental car. Grab your wheels from Dollar, Hertz or Budget and experience the lesser-explored corners of Chicago and beyond.

  • Secure the lowest price by reserving your vehicle from Chicago Midway International Airport about four weeks in advance of your trip.

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

  • MDW is located at 5700 South Cicero.

  • From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 20 minutes to get to the centre driving.

  • If you're taking public transport, expect a journey time of roughly 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • The quietest month for a flight from Pearson International Airport to Chicago Midway International Airport is May, while July is the most popular. Pick the best time to visit Chicago based on whether you prefer a more fast-paced or easygoing experience.

  • The warmest month in Chicago is July, with the temperature ranging between 15ºC and 29ºC. Lock in your flights from Pearson International Airport to Chicago Midway International Airport in this month if this is the type of weather you like.

  • Search for cheap tickets from YYZ to MDW in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

Explore more of United States

  • You've done Chicago, now it's time to discover other parts of United States. Journey around 451 kilometres south-east to Columbus to check off its must-visit sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you'll have a packed itinerary ahead.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. No visit is complete without checking out The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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