YYZ - MDW

$134 Find Cheap Flights from Toronto Pearson Airport to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pearson Intl to Midway departing on 9/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Booking Insights
Flights Deals

Cheap Flights from Pearson Intl to Midway (YYZ-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Pearson Intl to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Pearson Intl to Midway

Sat, Sep 13 - Sat, Sep 20
Delta Logo
12:14 pm - 6:35 pmYYZ-MDW
7h 21m1 stop
Delta Logo
6:15 pm - 10:56 pmMDW-YYZ
3h 41m1 stop
$212Delta
Find Deal
Thu, Sep 25 - Mon, Sep 29
Delta Logo
12:14 pm - 6:35 pmYYZ-MDW
7h 21m1 stop
Delta Logo
9:35 am - 5:23 pmMDW-YYZ
6h 48m1 stop
$213Delta
Find Deal
Fri, Sep 5 - Tue, Sep 16
Delta Logo
12:15 pm - 6:37 pmYYZ-MDW
7h 22m1 stop
Delta Logo
9:35 am - 5:23 pmMDW-YYZ
6h 48m1 stop
$225Delta
Find Deal
Wed, Aug 27 - Fri, Sep 5
Delta Logo
6:30 am - 12:28 pmYYZ-MDW
6h 58m1 stop
Delta Logo
9:30 am - 5:23 pmMDW-YYZ
6h 53m1 stop
$237Delta
Find Deal
Fri, Sep 12 - Fri, Sep 19
Delta Logo
4:12 pm - 6:35 pmYYZ-MDW
3h 23m1 stop
Delta Logo
9:29 am - 5:23 pmMDW-YYZ
6h 54m1 stop
$238Delta
Find Deal
Thu, Sep 4 - Mon, Sep 8
Delta Logo
6:30 am - 8:35 amYYZ-MDW
3h 05m1 stop
Delta Logo
1:43 pm - 11:33 pmMDW-YYZ
8h 50m1 stop
$240Delta
Find Deal
Thu, Aug 28 - Thu, Sep 4
Delta Logo
6:30 am - 12:28 pmYYZ-MDW
6h 58m1 stop
Delta Logo
9:30 am - 5:23 pmMDW-YYZ
6h 53m1 stop
$241Delta
Find Deal
Thu, Sep 4 - Sun, Sep 7
Delta Logo
6:30 am - 8:35 amYYZ-MDW
3h 05m1 stop
Delta Logo
9:31 am - 5:23 pmMDW-YYZ
6h 52m1 stop
$248Delta
Find Deal
Thu, Sep 4 - Mon, Sep 8
WestJet Logo
1:20 pm - 9:26 pmYYZ-MDW
9h 06m1 stop
WestJet Logo
10:31 am - 4:57 pmMDW-YYZ
5h 26m1 stop
$280WestJet
Find Deal
Tue, Oct 7 - Tue, Oct 21
WestJet Logo
6:00 pm - 10:14 pmYYZ-MDW
5h 14m1 stop
WestJet Logo
1:48 pm - 11:18 pmMDW-YYZ
8h 30m1 stop
$281WestJet
Find Deal
Booking Insights

KAYAK's insights & trends for Pearson Intl to Midway flights

Get data-powered insights and trends into flights from Pearson Intl to Midway to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Toronto Pearson Intl Airport to Chicago Midway Airport?

What is the cheapest month to fly from Toronto Pearson Intl Airport to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Toronto Pearson Intl Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Toronto Pearson Intl Airport to Chicago Midway Airport is February, where tickets cost $219 (return) on average. On the other hand, the most expensive months are August and October, where the average cost of round-trip tickets is $406 and $377 respectively.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$134
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly with an average 31% increase in price.
Flight from Toronto Pearson Airport to Chicago Midway Airport

When to book flights from Pearson Intl to Midway

Are your dates flexible? Find out the best times to travel from Pearson Intl to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Toronto Pearson Airport to Chicago Midway Airport flights

  • What is the cheapest flight from Toronto Pearson Intl Airport to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Toronto Pearson Intl Airport to Chicago Midway Airport was $134 for a one-way ticket and $212 for a round-trip.

  • Do I need a passport to fly between Toronto Pearson Airport and Chicago Midway Airport?

    A passport is required to fly from Toronto Pearson Airport to Chicago Midway Airport.

  • Which airports will I be using when flying from Toronto Pearson Airport to Chicago Midway Airport?

    Toronto Pearson Airport airport is called Toronto Pearson Intl and the only airport in Chicago Midway Airport is Chicago Midway.

  • Which aircraft models fly most regularly from Toronto Pearson Airport to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Toronto Pearson Airport to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Toronto Pearson Airport and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights from Toronto Pearson Airport to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Toronto Pearson Airport to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Toronto Pearson Airport to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Toronto Pearson Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Toronto Pearson Airport to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Toronto Pearson Airport with another airline. Booking your flights between Toronto Pearson Airport and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto Pearson Airport to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Toronto Pearson Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight from Pearson Intl to Midway

Information on your arrival and departure airports

Toronto Pearson Airport (YYZ)
Midway (MDW)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.