YYZ - MDW

C$ 195 Find Cheap Flights from Toronto Pearson Airport to Chicago Midway Airport – Compare and Save

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 1/9. 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, 0 bags

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Everything you should know

Cheapest round-trip
C$ 332
Typical prices: C$ 426-C$ 797
Delta
Tue 1/9Sat 12/9
YYZ - MDW • 1 stop
Cheapest one-way flights
C$ 195
Delta
Tue 1/9
YYZ - MDW • 1 stop
Direct flights
Not available
There are currently no direct flights between Pearson Intl and Midway. You’ll need at least 1 connection.
Insights
Insights
Insights
Insights
Avoid delays
Delta
Most punctual • 45% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 100% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight 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

Tue, 1 Sep - Sat, 12 Sep
Delta Logo
6:10 a.m. - 9:17 a.m.
YYZ
-
MDW
4h 07m
1 stop
Delta Logo
5:37 p.m. - 10:59 p.m.
MDW
-
YYZ
4h 22m
1 stop
C$ 332Delta
Sun, 6 Sep - Sat, 12 Sep
Delta Logo
12:09 p.m. - 4:59 p.m.
YYZ
-
MDW
5h 50m
1 stop
Delta Logo
5:37 p.m. - 10:59 p.m.
MDW
-
YYZ
4h 22m
1 stop
C$ 332Delta
Sat, 5 Sep - Sat, 12 Sep
Delta Logo
6:10 a.m. - 9:17 a.m.
YYZ
-
MDW
4h 07m
1 stop
Delta Logo
5:37 p.m. - 10:59 p.m.
MDW
-
YYZ
4h 22m
1 stop
C$ 332Delta
Wed, 2 Sep - Fri, 11 Sep
Delta Logo
6:10 a.m. - 9:17 a.m.
YYZ
-
MDW
4h 07m
1 stop
Delta Logo
5:03 p.m. - 10:59 p.m.
MDW
-
YYZ
4h 56m
1 stop
C$ 332Delta
Sat, 5 Sep - Fri, 11 Sep
Delta Logo
6:10 a.m. - 9:17 a.m.
YYZ
-
MDW
4h 07m
1 stop
Delta Logo
5:03 p.m. - 10:59 p.m.
MDW
-
YYZ
4h 56m
1 stop
C$ 332Delta
Wed, 2 Sep - Sat, 12 Sep
Delta Logo
6:10 a.m. - 9:17 a.m.
YYZ
-
MDW
4h 07m
1 stop
Delta Logo
5:37 p.m. - 10:59 p.m.
MDW
-
YYZ
4h 22m
1 stop
C$ 332Delta
Fri, 4 Sep - Fri, 11 Sep
Delta Logo
4:10 p.m. - 6:33 p.m.
YYZ
-
MDW
3h 23m
1 stop
Delta Logo
5:03 p.m. - 10:59 p.m.
MDW
-
YYZ
4h 56m
1 stop
C$ 332Delta
Tue, 1 Sep - Fri, 11 Sep
Delta Logo
6:10 a.m. - 9:17 a.m.
YYZ
-
MDW
4h 07m
1 stop
Delta Logo
5:03 p.m. - 10:59 p.m.
MDW
-
YYZ
4h 56m
1 stop
C$ 332Delta
Sat, 5 Sep - Fri, 11 Sep
Delta Logo
12:09 p.m. - 4:59 p.m.
YYZ
-
MDW
5h 50m
1 stop
Delta Logo
5:03 p.m. - 10:59 p.m.
MDW
-
YYZ
4h 56m
1 stop
C$ 343Delta
Sat, 5 Sep - Tue, 15 Sep
Delta Logo
9:45 a.m. - 4:59 p.m.
YYZ
-
MDW
8h 14m
1 stop
Delta Logo
9:29 a.m. - 5:20 p.m.
MDW
-
YYZ
6h 51m
1 stop
C$ 343Delta
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.

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 January, where tickets cost C$ 0 (return) on average. On the other hand, the most expensive months are April and August, where the average cost of round-trip tickets is C$ 759 and C$ 604 respectively.

Find deals

Good to know

Low season

December

Cheapest flight

C$ 195
Best time to beat the crowds (38% less expensive on average)
Most popular time to fly and prices are also 18% lower on average.
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 5 days, the lowest price for a flight from Toronto Pearson Intl Airport to Chicago Midway Airport was C$ 195 for a one-way ticket and C$ 332 for a round-trip.

  • 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.

  • 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 travellers 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.

  • 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)