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Find cheap flights from Toronto Pearson Airport to Chicago Midway Airport from $159

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 5/14. 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
0 bags
Sat 6/8
Sat 6/15

Search 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
In the last 7 days travelers have searched 43,968,530 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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

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

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

Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
6:04 am - 9:06 amYYZ-MDW
4h 02m1 stop
1:21 pm - 10:46 pmMDW-YYZ
8h 25m1 stop
$267Delta
Find Deal
Mon, May 27 - Fri, May 31
12:30 pm - 4:55 pmYYZ-MDW
5h 25m1 stop
1:21 pm - 10:46 pmMDW-YYZ
8h 25m1 stop
$270Delta
Find Deal
Sat, May 25 - Tue, May 28
12:30 pm - 4:55 pmYYZ-MDW
5h 25m1 stop
1:21 pm - 10:46 pmMDW-YYZ
8h 25m1 stop
$271Delta
Find Deal
Sat, May 25 - Tue, May 28
6:04 am - 8:40 amYYZ-MDW
3h 36m1 stop
5:45 pm - 10:50 pmMDW-YYZ
4h 05m1 stop
$296Delta
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Thu, Jul 11 - Tue, Jul 16
9:45 am - 5:04 pmYYZ-MDW
8h 19m1 stop
9:29 am - 5:08 pmMDW-YYZ
6h 39m1 stop
$297Delta
Find Deal
Thu, Jun 13 - Mon, Jul 1
12:30 pm - 5:06 pmYYZ-MDW
5h 36m1 stop
9:34 am - 5:08 pmMDW-YYZ
6h 34m1 stop
$298Delta
Find Deal
Wed, Jun 5 - Wed, Jun 12
6:45 am - 6:06 pmYYZ-MDW
12h 21m1 stop
3:45 pm - 9:58 pmMDW-YYZ
5h 13m1 stop
$300WestJet
Find Deal
Sat, Aug 17 - Tue, Aug 20
12:30 pm - 6:06 pmYYZ-MDW
6h 36m1 stop
10:11 am - 4:53 pmMDW-YYZ
5h 42m1 stop
$311WestJet
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Sun, Sep 1 - Sat, Sep 7
6:34 am - 11:02 amYYZ-MDW
5h 28m1 stop
4:41 pm - 11:57 pmMDW-YYZ
6h 16m1 stop
$316WestJet
Find Deal
Sun, May 26 - Wed, May 29
8:00 pm - 6:33 amYYZ-MDW
11h 33m1 stop
10:00 pm - 8:49 pmMDW-YYZ
21h 49m2 stops
$412
Find Deal
Sat, Aug 17 - Tue, Aug 20

Flights from Pearson Intl to Midway - Travel Insights & Trends

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 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 March, where tickets cost $216 on average. On the other hand, the most expensive months are June and August, where the average cost of tickets is $380 and $342 respectively.

How far in advance should I book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Toronto Pearson Intl Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Toronto Pearson Intl Airport to Chicago Midway Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 16 days before departure.

Which airlines provide the cheapest flights from Toronto Pearson Airport to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the past 3 days, the cheapest one-way tickets to Chicago Midway Airport from Toronto Pearson Airport were found on Delta ($163) and WestJet ($170), and the lowest round-trip tickets were found on Delta ($267) and WestJet ($300).

Good to know

Low season

January

High season

February

Cheapest flight

$159
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 39% 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 3 days, the lowest price for a flight from Toronto Pearson Intl Airport to Chicago Midway Airport was $159 for a one-way ticket and $267 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.

See more FAQs

Book cheap flights from Toronto to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Toronto to Chicago found on KAYAK in the last 72 hours.
5/14Tue
1 stop
16h 36mYYZ-MDW
$159
5/14Tue
1 stop
16h 36mYYZ-MDW
$161
6/9Sun
1 stopDelta
5h 34mYYZ-MDW
$163
6/14Fri
2 stopsWestJet
15h 51mYYZ-MDW
$170
5/26Sun
1 stopWestJet
5h 28mYYZ-MDW
$174
5/22Wed
1 stopWestJet
6h 37mYYZ-MDW
$179
7/1Mon
1 stopWestJet
13h 01mYYZ-MDW
$180
6/2Sun
1 stopDelta
4h 02mYYZ-MDW
$189
5/27Mon
1 stop
10h 50mYYZ-MDW
$206
5/15Wed
1 stopDelta
5h 36mYYZ-MDW
$225

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Last minute flights from Pearson Intl to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Toronto to Chicago that are departing in the next 10 days.
5/11Sat
multi-stop
12h 47mYYZ-MDW
5/14Tue
multi-stop
30h 43mMDW-YYZ
$424
5/13Mon
multi-stop
16h 36mYYZ-MDW
5/15Wed
multi-stop
20h 32mMDW-YYZ
$430
5/11Sat
multi-stop
11h 21mYYZ-MDW
5/14Tue
multi-stop
30h 43mMDW-YYZ
$448
5/12Sun
multi-stopWestJet
5h 07mYYZ-MDW
5/18Sat
multi-stopWestJet
5h 14mMDW-YYZ
$454
5/13Mon
multi-stopDelta
8h 21mYYZ-MDW
5/18Sat
multi-stopDelta
5h 14mMDW-YYZ
$465
5/12Sun
multi-stopWestJet
6h 35mYYZ-MDW
5/15Wed
multi-stopWestJet
5h 10mMDW-YYZ
$466
5/12Sun
multi-stopDelta
7h 36mYYZ-MDW
5/15Wed
multi-stopDelta
7h 59mMDW-YYZ
$472
5/11Sat
multi-stopDelta
3h 47mYYZ-MDW
5/12Sun
multi-stopDelta
7h 59mMDW-YYZ
$509
5/12Sun
multi-stopWestJet
9h 36mYYZ-MDW
5/15Wed
multi-stopWestJet
24h 13mMDW-YYZ
$517
5/13Mon
multi-stop
16h 36mYYZ-MDW
5/15Wed
multi-stop
7h 04mMDW-YYZ
$557

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Toronto Pearson Airport - Chicago Midway Airport Flights

Departure:

Toronto Pearson Airport (undefined)Canada

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Toronto Pearson Airport

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