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$125 Find cheap flights from Chicago Midway Airport to Toronto Pearson 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 Midway to Pearson Intl departing on 6/18. 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 6/15
Sat 6/22

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 42,211,976 times on KAYAK, and here is why:

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

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Cheap flight deals from Midway to Pearson Intl (MDW-YYZ)

 
These are the cheapest deals for flights from Midway to Pearson Intl currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to Pearson Intl

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Pearson Intl.

Recent one-way flight deals from Midway to Pearson Intl

Only flying one-way? Below are some of the best one-way flight deals from Midway to Pearson Intl found on KAYAK recently.

Recent last minute flight deals from Midway to Pearson Intl

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Midway to Pearson Intl.

Recent direct flight deals from Midway to Pearson Intl

The latest deals for direct flights from Midway to Pearson Intl so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Midway to Pearson Intl

Find recent round-trip train or bus tickets from Midway to Pearson Intl.

All round-trip flight deals to Pearson Intl

The cheapest plane tickets to Pearson Intl found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
1:21 pm - 10:46 pmMDW-YYZ
8h 25m1 stop
9:45 am - 5:04 pmYYZ-MDW
8h 19m1 stop
$287Delta
Find Deal
Thu, Jun 6 - Mon, Jun 10
5:45 pm - 10:53 pmMDW-YYZ
4h 08m1 stop
12:30 pm - 5:04 pmYYZ-MDW
5h 34m1 stop
$312KLM
Find Deal
Tue, Jul 16 - Tue, Jul 23
9:46 am - 6:20 pmMDW-YYZ
7h 34m1 stop
9:45 am - 5:06 pmYYZ-MDW
8h 21m1 stop
$317Delta
Find Deal
Wed, May 29 - Thu, Jun 6
9:34 am - 5:08 pmMDW-YYZ
6h 34m1 stop
12:31 pm - 6:30 pmYYZ-MDW
6h 59m1 stop
$328Delta
Find Deal
Wed, Jun 12 - Sat, Jun 15
9:34 am - 5:08 pmMDW-YYZ
6h 34m1 stop
12:31 pm - 6:36 pmYYZ-MDW
7h 05m1 stop
$339Delta
Find Deal
Wed, Jun 12 - Wed, Jun 19
9:46 am - 6:20 pmMDW-YYZ
7h 34m1 stop
6:04 pm - 10:01 pmYYZ-MDW
4h 57m1 stop
$349WestJet
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Wed, May 29 - Wed, Jun 5
9:33 am - 5:08 pmMDW-YYZ
6h 35m1 stop
6:15 am - 8:44 amYYZ-MDW
3h 29m1 stop
$354Delta
Find Deal
Thu, Aug 1 - Sun, Aug 25
6:00 am - 12:10 pmMDW-YYZ
5h 10m1 stop
7:45 am - 11:44 amYYZ-MDW
4h 59m1 stop
$358WestJet
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Thu, Jul 4 - Mon, Jul 8
9:29 am - 6:33 pmMDW-YYZ
8h 04m1 stop
12:31 pm - 6:36 pmYYZ-MDW
7h 05m1 stop
$364Delta
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Thu, Jun 13 - Wed, Jun 19
2:15 pm - 11:14 pmMDW-YYZ
7h 59m1 stop
1:25 pm - 10:01 pmYYZ-MDW
9h 36m1 stop
$376WestJet
Find Deal
Wed, May 29 - Wed, Jun 5
7:54 pm - 6:45 amMDW-YYZ
9h 51m1 stop
$125
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Tue, Jun 18
9:34 am - 5:08 pmMDW-YYZ
6h 34m1 stop
$132Delta
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Tue, Jun 11
8:53 pm - 12:22 amMDW-YYZ
26h 29m1 stop
$138
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Sun, Jun 9
9:34 am - 5:08 pmMDW-YYZ
6h 34m1 stop
$142Delta
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Wed, Jun 12
8:56 pm - 11:26 pmMDW-YYZ
25h 30m1 stop
$145
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Mon, Jun 3
9:20 am - 6:21 pmMDW-YYZ
8h 01m1 stop
$147KLM
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Tue, Sep 10
6:00 am - 12:10 pmMDW-YYZ
5h 10m1 stop
$155WestJet
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Wed, Jun 5
10:11 am - 4:53 pmMDW-YYZ
5h 42m1 stop
$158WestJet
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Sat, Aug 10
5:00 pm - 11:14 pmMDW-YYZ
5h 14m1 stop
$161WestJet
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Sat, Jun 1
2:15 pm - 11:14 pmMDW-YYZ
7h 59m1 stop
$166KLM
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Tue, May 28
9:46 am - 6:20 pmMDW-YYZ
7h 34m1 stop
6:34 am - 1:35 pmYYZ-MDW
8h 01m1 stop
$581WestJet
Find Deal
Sun, May 19 - Wed, May 22
1:21 pm - 10:46 pmMDW-YYZ
8h 25m1 stop
6:04 am - 9:06 amYYZ-MDW
4h 02m1 stop
$582Delta
Find Deal
Tue, May 21 - Wed, May 29
9:46 am - 11:14 pmMDW-YYZ
12h 28m1 stop
12:30 pm - 6:07 pmYYZ-MDW
6h 37m1 stop
$588WestJet
Find Deal
Sun, May 19 - Tue, May 21
2:15 pm - 11:14 pmMDW-YYZ
7h 59m1 stop
12:30 pm - 11:02 amYYZ-MDW
23h 32m1 stop
$613WestJet
Find Deal
Mon, May 20 - Sat, May 25
8:45 am - 9:57 pmMDW-YYZ
12h 12m1 stop
12:30 pm - 6:07 pmYYZ-MDW
6h 37m1 stop
$620WestJet
Find Deal
Tue, May 21 - Wed, May 22
9:46 am - 6:20 pmMDW-YYZ
7h 34m1 stop
12:30 pm - 6:07 pmYYZ-MDW
6h 37m1 stop
$631WestJet
Find Deal
Fri, May 17 - Sun, May 19
9:46 am - 6:20 pmMDW-YYZ
7h 34m1 stop
6:34 am - 1:35 pmYYZ-MDW
8h 01m1 stop
$632WestJet
Find Deal
Fri, May 17 - Wed, May 22
2:15 pm - 11:14 pmMDW-YYZ
7h 59m1 stop
10:15 pm - 11:02 amYYZ-MDW
13h 47m2 stops
$648WestJet
Find Deal
Mon, May 20 - Sat, May 25
5:00 pm - 11:14 pmMDW-YYZ
5h 14m1 stop
12:30 pm - 5:06 pmYYZ-MDW
5h 36m1 stop
$653Delta
Find Deal
Sat, May 18 - Mon, May 20
1:15 pm - 11:26 pmMDW-YYZ
9h 11m1 stop
7:45 am - 10:04 pmYYZ-MDW
15h 19m2 stops
$656
Find Deal
Fri, May 17 - Mon, May 20

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 October, where the average cost of tickets is $424 and $387 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 KLM ($147). The cheapest round-trip tickets were found on Delta ($287) and KLM ($312).

Good to know

Low season

May

High season

June

Cheapest flight

$125
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 $125 for a one-way ticket and $287 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.
6/18Tue
1 stop
9h 51mMDW-YYZ
$125
6/11Tue
1 stopDelta
6h 34mMDW-YYZ
$132
6/9Sun
1 stop
26h 29mMDW-YYZ
$138
6/12Wed
1 stopDelta
6h 34mMDW-YYZ
$142
6/3Mon
1 stop
25h 30mMDW-YYZ
$145
9/10Tue
1 stopKLM
8h 01mMDW-YYZ
$147
6/5Wed
1 stopWestJet
5h 10mMDW-YYZ
$155
8/10Sat
1 stopWestJet
5h 42mMDW-YYZ
$158
6/1Sat
1 stopWestJet
5h 14mMDW-YYZ
$161
5/28Tue
1 stopKLM
7h 59mMDW-YYZ
$166

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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.
5/19Sun
multi-stopWestJet
7h 34mMDW-YYZ
5/22Wed
multi-stopWestJet
8h 01mYYZ-MDW
$581
5/21Tue
multi-stopDelta
8h 25mMDW-YYZ
5/29Wed
multi-stopDelta
4h 02mYYZ-MDW
$582
5/19Sun
multi-stopWestJet
12h 28mMDW-YYZ
5/21Tue
multi-stopWestJet
6h 37mYYZ-MDW
$588
5/20Mon
multi-stopWestJet
7h 59mMDW-YYZ
5/25Sat
multi-stopWestJet
23h 32mYYZ-MDW
$613
5/21Tue
multi-stopWestJet
12h 12mMDW-YYZ
5/22Wed
multi-stopWestJet
6h 37mYYZ-MDW
$620
5/17Fri
multi-stopWestJet
7h 34mMDW-YYZ
5/19Sun
multi-stopWestJet
6h 37mYYZ-MDW
$631
5/17Fri
multi-stopWestJet
7h 34mMDW-YYZ
5/22Wed
multi-stopWestJet
8h 01mYYZ-MDW
$632
5/20Mon
multi-stopWestJet
7h 59mMDW-YYZ
5/25Sat
multi-stopWestJet
13h 47mYYZ-MDW
$648
5/18Sat
multi-stopDelta
5h 14mMDW-YYZ
5/20Mon
multi-stopDelta
5h 36mYYZ-MDW
$653
5/17Fri
multi-stop
9h 11mMDW-YYZ
5/20Mon
multi-stop
15h 19mYYZ-MDW
$656

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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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