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MDW - YYZ

Find cheap flights from Chicago Midway Airport to Toronto Pearson Airport from C$ 164

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 8/5. 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
Wed 29/5
Wed 5/6

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, travellers have searched 43,983,279 times on KAYAK, and here is why:

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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
9:20 a.m. - 5:08 p.m.MDW-YYZ
6h 48m1 stop
6:04 a.m. - 8:40 a.m.YYZ-MDW
3h 36m1 stop
C$ 458Delta
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Sat, 27 Jul - Wed, 31 Jul
9:32 a.m. - 5:09 p.m.MDW-YYZ
6h 37m1 stop
6:04 a.m. - 9:06 a.m.YYZ-MDW
4h 02m1 stop
C$ 459Delta
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Fri, 31 May - Sun, 2 Jun
5:00 p.m. - 11:14 p.m.MDW-YYZ
5h 14m1 stop
12:30 p.m. - 4:55 p.m.YYZ-MDW
5h 25m1 stop
C$ 473Delta
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Sat, 11 May - Sat, 18 May
2:15 p.m. - 11:14 p.m.MDW-YYZ
7h 59m1 stop
12:30 p.m. - 5:06 p.m.YYZ-MDW
5h 36m1 stop
C$ 488Delta
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Mon, 13 May - Wed, 15 May
5:45 p.m. - 10:50 p.m.MDW-YYZ
4h 05m1 stop
6:30 a.m. - 1:05 p.m.YYZ-MDW
7h 35m1 stop
C$ 489Delta
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Sat, 27 Jul - Tue, 30 Jul
5:45 p.m. - 10:50 p.m.MDW-YYZ
4h 05m1 stop
12:31 p.m. - 6:31 p.m.YYZ-MDW
7h 00m1 stop
C$ 493Delta
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Sat, 29 Jun - Tue, 2 Jul
9:46 a.m. - 11:14 p.m.MDW-YYZ
12h 28m1 stop
7:46 a.m. - 5:59 p.m.YYZ-MDW
11h 13m1 stop
C$ 499WestJet
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Wed, 5 Jun - Wed, 12 Jun
12:45 p.m. - 11:59 p.m.MDW-YYZ
10h 14m1 stop
6:30 a.m. - 6:36 p.m.YYZ-MDW
13h 06m1 stop
C$ 525WestJet
Find Deal
Fri, 14 Jun - Mon, 17 Jun
2:15 p.m. - 11:14 p.m.MDW-YYZ
7h 59m1 stop
12:30 p.m. - 6:07 p.m.YYZ-MDW
6h 37m1 stop
C$ 534WestJet
Find Deal
Wed, 29 May - Wed, 5 Jun
6:00 a.m. - 12:10 p.m.MDW-YYZ
5h 10m1 stop
8:20 p.m. - 5:50 a.m.YYZ-MDW
10h 30m1 stop
C$ 675
Find Deal
Thu, 16 May - Sat, 18 May

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 January, where tickets cost C$ 343 on average. On the other hand, the most expensive months are July and September, where the average cost of tickets is C$ 629 and C$ 564 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 5 days before departure. For the absolute cheapest price, our data suggests you should book 66 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 (C$ 194) and WestJet (C$ 216). The cheapest round-trip tickets were found on Delta (C$ 458) and WestJet (C$ 499).

Good to know

Cheapest flight

C$ 164
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 C$ 120 for a one-way ticket and C$ 335 for a round-trip.

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

    On your way to Toronto Pearson Airport, you’ll fly out from Chicago Midway. You’ll be landing at Toronto Pearson Intl.

  • 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 travellers 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.

  • 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.
8/5Wed
1 stop
30h 36mMDW-YYZ
C$ 164
7/5Tue
1 stop
30h 43mMDW-YYZ
C$ 172
18/6Tue
1 stopDelta
7h 48mMDW-YYZ
C$ 194
13/5Mon
1 stopDelta
7h 59mMDW-YYZ
C$ 209
20/6Thu
1 stopWestJet
8h 14mMDW-YYZ
C$ 216
30/6Sun
1 stopWestJet
5h 10mMDW-YYZ
C$ 224
6/6Thu
1 stopDelta
7h 59mMDW-YYZ
C$ 230
18/6Tue
1 stopWestJet
5h 14mMDW-YYZ
C$ 232
22/5Wed
1 stopDelta
8h 25mMDW-YYZ
C$ 249
11/6Tue
2 stops
15h 29mMDW-YYZ
C$ 279

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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.
2/5Thu
multi-stop
5h 10mMDW-YYZ
7/5Tue
multi-stop
16h 16mYYZ-MDW
C$ 662
1/5Wed
multi-stopWestJet
6h 00mMDW-YYZ
18/5Sat
multi-stopWestJet
5h 25mYYZ-MDW
C$ 715
3/5Fri
multi-stopWestJet
5h 54mMDW-YYZ
7/5Tue
multi-stopWestJet
4h 57mYYZ-MDW
C$ 731
2/5Thu
multi-stopWestJet
5h 10mMDW-YYZ
6/5Mon
multi-stopWestJet
10h 32mYYZ-MDW
C$ 767
2/5Thu
multi-stopWestJet
10h 33mMDW-YYZ
7/5Tue
multi-stopWestJet
4h 57mYYZ-MDW
C$ 789
30/4Tue
multi-stopWestJet
10h 11mMDW-YYZ
7/5Tue
multi-stopWestJet
4h 57mYYZ-MDW
C$ 790
1/5Wed
multi-stopDelta
8h 19mMDW-YYZ
8/5Wed
multi-stopDelta
5h 36mYYZ-MDW
C$ 798
2/5Thu
multi-stopDelta
6h 39mMDW-YYZ
6/5Mon
multi-stopDelta
7h 38mYYZ-MDW
C$ 815
30/4Tue
multi-stopDelta
8h 21mMDW-YYZ
6/5Mon
multi-stopDelta
7h 38mYYZ-MDW
C$ 873
2/5Thu
multi-stop
14h 19mMDW-YYZ
6/5Mon
multi-stop
15h 20mYYZ-MDW
C$ 2,470

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Chicago Midway Airport - Toronto Pearson Airport Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Toronto Pearson Airport (YYZ)Canada

Return flight deals:

Toronto Pearson Airport - Chicago Midway Airport

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