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Find cheap flights from Chicago Midway Airport to Toronto Pearson Airport from $132

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Pearson Intl departing on 6/6. 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
Thu 6/6
Thu 6/13

Search hundreds of travel sites at once for deals on flights to Toronto Pearson Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Toronto, 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 Chicago to Toronto, as well as popular online travel agencies
In the last 7 days travelers have searched 43,707,506 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 Midway to Pearson Intl (MDW-YYZ)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Pearson Intl 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
2:15 pm - 11:14 pmMDW-YYZ
7h 59m1 stop
6:04 am - 8:48 amYYZ-MDW
3h 44m1 stop
$317Delta
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Wed, Jun 5 - Sun, Jun 9
2:15 pm - 11:14 pmMDW-YYZ
7h 59m1 stop
6:04 am - 9:06 amYYZ-MDW
4h 02m1 stop
$338Delta
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Thu, May 30 - Sun, Jun 2
9:46 am - 11:14 pmMDW-YYZ
12h 28m1 stop
6:04 pm - 10:01 pmYYZ-MDW
4h 57m1 stop
$349WestJet
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Tue, May 28 - Wed, Jun 5
9:46 am - 6:20 pmMDW-YYZ
7h 34m1 stop
12:30 pm - 6:07 pmYYZ-MDW
6h 37m1 stop
$354Delta
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Wed, May 29 - Wed, Jun 5
2:15 pm - 11:14 pmMDW-YYZ
7h 59m1 stop
12:30 pm - 5:04 pmYYZ-MDW
5h 34m1 stop
$364Delta
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Tue, Jun 4 - Tue, Jun 11
4:41 pm - 11:57 pmMDW-YYZ
6h 16m1 stop
6:04 pm - 10:01 pmYYZ-MDW
4h 57m1 stop
$367WestJet
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Wed, Jun 5 - Thu, Jun 6
5:00 pm - 5:45 amMDW-YYZ
11h 45m2 stops
1:20 pm - 5:14 pmYYZ-MDW
4h 54m1 stop
$379WestJet
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Sat, Aug 17 - Sat, Aug 24
6:00 am - 9:59 pmMDW-YYZ
14h 59m1 stop
11:37 am - 11:55 amYYZ-MDW
25h 18m1 stop
$382WestJet
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Tue, Jun 18 - Wed, Jun 19
6:00 am - 4:49 pmMDW-YYZ
9h 49m1 stop
12:30 pm - 6:07 pmYYZ-MDW
6h 37m1 stop
$385WestJet
Find Deal
Tue, May 28 - Wed, May 29
6:00 am - 12:10 pmMDW-YYZ
5h 10m1 stop
8:00 pm - 5:29 amYYZ-MDW
10h 29m1 stop
$386
Find Deal
Wed, Jun 19 - Wed, Jun 19

Flights from Midway to Pearson Intl - Travel Insights & Trends

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Toronto Pearson Intl 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 Chicago Midway Airport to Toronto Pearson Intl Airport is February, where tickets cost $285 on average. On the other hand, the most expensive months are July and September, where the average cost of tickets is $446 and $398 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Toronto Pearson Intl 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 Chicago Midway Airport to Toronto Pearson Intl Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 56 days before departure.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Delta ($132) and WestJet ($156). The cheapest round-trip tickets were found on Delta ($317) and WestJet ($349).

Good to know

Low season

May

High season

June

Cheapest flight

$132
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 34% increase in price.
Flight from Chicago Midway Airport to Toronto Pearson Airport

When to book flights from Midway to Pearson Intl

Are your dates flexible? Find out the best times to travel from Midway to Pearson Intl 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 Chicago Midway Airport to Toronto Pearson Airport flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Toronto Pearson Intl Airport was $132 for a one-way ticket and $317 for a round-trip.

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

    Yes, you’ll need a passport to travel to Toronto Pearson Airport from Chicago Midway Airport.

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

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

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

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

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Toronto Pearson Airport from Chicago Midway 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 Chicago Midway Airport to Toronto Pearson 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 Toronto Pearson Airport with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and YYZ 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 Chicago Midway Airport to Toronto Pearson 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 Toronto Pearson Airport from Chicago Midway 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 Chicago to Toronto

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Toronto found on KAYAK in the last 72 hours.
6/6Thu
1 stopDelta
7h 59mMDW-YYZ
$132
6/8Sat
1 stopDelta
6h 40mMDW-YYZ
$142
8/12Mon
1 stop
11h 44mMDW-YYZ
$145
8/12Mon
1 stop
11h 44mMDW-YYZ
$151
5/14Tue
1 stop
30h 43mMDW-YYZ
$155
7/6Sat
1 stopWestJet
15h 27mMDW-YYZ
$156
6/11Tue
1 stopWestJet
5h 10mMDW-YYZ
$157
5/14Tue
1 stop
22h 01mMDW-YYZ
$158
6/5Wed
1 stopWestJet
7h 04mMDW-YYZ
$160
7/3Wed
1 stopDelta
7h 48mMDW-YYZ
$168

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Last minute flights from Midway to Pearson Intl

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 Chicago to Toronto that are departing in the next 10 days.
5/11Sat
multi-stop
5h 10mMDW-YYZ
5/14Tue
multi-stop
16h 16mYYZ-MDW
$483
5/11Sat
multi-stop
5h 14mMDW-YYZ
5/13Mon
multi-stop
16h 36mYYZ-MDW
$530
5/10Fri
multi-stopWestJet
7h 34mMDW-YYZ
5/14Tue
multi-stopWestJet
6h 37mYYZ-MDW
$538
5/8Wed
multi-stopDelta
7h 59mMDW-YYZ
5/30Thu
multi-stopDelta
4h 02mYYZ-MDW
$553
5/12Sun
multi-stopWestJet
12h 28mMDW-YYZ
5/17Fri
multi-stopWestJet
22h 45mYYZ-MDW
$554
5/10Fri
multi-stopWestJet
7h 04mMDW-YYZ
5/12Sun
multi-stopWestJet
4h 57mYYZ-MDW
$569
5/12Sun
multi-stop
5h 10mMDW-YYZ
5/12Sun
multi-stop
7h 29mYYZ-MDW
$573
5/9Thu
multi-stopWestJet
14h 57mMDW-YYZ
5/14Tue
multi-stopWestJet
4h 57mYYZ-MDW
$593
5/11Sat
multi-stopDelta
6h 37mMDW-YYZ
5/13Mon
multi-stopDelta
8h 21mYYZ-MDW
$599
5/12Sun
multi-stopDelta
7h 59mMDW-YYZ
5/17Fri
multi-stopDelta
8h 21mYYZ-MDW
$628

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Chicago Midway Airport - Toronto Pearson Airport Flights

Departure:

Chicago Midway Airport (undefined)United States

Destination:

Toronto Pearson Airport (YYZ)Canada

Return flight deals:

Toronto Pearson Airport - Chicago Midway Airport

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