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Find cheap flights from Toronto Pearson Airport to Chicago Midway Airport from $138

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 5/7. 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
Sun 5/26
Sun 6/2

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 44,738,066 times on KAYAK, and here is why:

Save 22% 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.

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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
12:30 pm - 5:06 pmYYZ-MDW
5h 36m1 stop
9:32 am - 5:09 pmMDW-YYZ
6h 37m1 stop
$258Delta
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Thu, May 23 - Thu, May 30
6:04 am - 12:40 pmYYZ-MDW
7h 36m1 stop
2:24 pm - 11:12 pmMDW-YYZ
7h 48m1 stop
$271Delta
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Mon, May 27 - Tue, Jun 11
12:30 pm - 6:07 pmYYZ-MDW
6h 37m1 stop
2:24 pm - 11:12 pmMDW-YYZ
7h 48m1 stop
$284Delta
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Thu, May 30 - Tue, Jun 11
12:30 pm - 4:13 pmYYZ-MDW
4h 43m1 stop
1:21 pm - 10:46 pmMDW-YYZ
8h 25m1 stop
$295Delta
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Sat, May 18 - Wed, May 22
12:30 pm - 4:55 pmYYZ-MDW
5h 25m1 stop
9:32 am - 5:09 pmMDW-YYZ
6h 37m1 stop
$299Delta
Find Deal
Sat, May 11 - Tue, May 14
6:04 am - 8:40 amYYZ-MDW
3h 36m1 stop
5:59 pm - 10:50 pmMDW-YYZ
3h 51m1 stop
$302Delta
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Wed, Jul 31 - Sat, Aug 10
6:04 am - 12:44 pmYYZ-MDW
7h 40m1 stop
9:35 am - 5:10 pmMDW-YYZ
6h 35m1 stop
$318KLM
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Sun, Aug 4 - Fri, Aug 9
7:10 pm - 11:02 amYYZ-MDW
16h 52m1 stop
6:00 am - 12:10 pmMDW-YYZ
5h 10m1 stop
$327WestJet
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Fri, May 10 - Sun, May 12
7:10 pm - 11:02 amYYZ-MDW
16h 52m1 stop
6:00 am - 12:10 pmMDW-YYZ
5h 10m1 stop
$328WestJet
Find Deal
Fri, May 10 - Sun, May 12
10:15 am - 9:31 pmYYZ-MDW
12h 16m2 stops
6:00 am - 12:10 pmMDW-YYZ
5h 10m1 stop
$476
Find Deal
Tue, May 21 - Wed, May 22

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 $221 on average. On the other hand, the most expensive months are January and June, where the average cost of tickets is $383 and $377 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 62 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 ($155) and KLM ($166), and the lowest round-trip tickets were found on Delta ($258) and KLM ($318).

Good to know

Low season

February

High season

July

Cheapest flight

$138
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 8% 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 $138 for a one-way ticket and $258 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.
5/7Tue
1 stop
16h 16mYYZ-MDW
$138
5/7Tue
1 stop
16h 16mYYZ-MDW
$150
5/7Tue
1 stop
16h 16mYYZ-MDW
$151
6/18Tue
1 stopDelta
3h 44mYYZ-MDW
$155
6/25Tue
1 stopKLM
3h 44mYYZ-MDW
$166
6/30Sun
1 stopDelta
5h 57mYYZ-MDW
$168
5/9Thu
1 stopDelta
3h 55mYYZ-MDW
$176
5/26Sun
1 stopWestJet
5h 28mYYZ-MDW
$180
6/1Sat
1 stopWestJet
5h 25mYYZ-MDW
$183
6/1Sat
1 stopWestJet
5h 25mYYZ-MDW
$184

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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.
4/30Tue
multi-stopDelta
3h 35mYYZ-MDW
5/6Mon
multi-stopDelta
8h 21mMDW-YYZ
$440
4/30Tue
multi-stopWestJet
5h 10mYYZ-MDW
5/21Tue
multi-stopWestJet
5h 10mMDW-YYZ
$442
4/30Tue
multi-stopWestJet
4h 52mYYZ-MDW
5/3Fri
multi-stopWestJet
5h 10mMDW-YYZ
$445
4/27Sat
multi-stopWestJet
4h 37mYYZ-MDW
5/13Mon
multi-stopWestJet
9h 49mMDW-YYZ
$457
4/28Sun
multi-stopWestJet
5h 10mYYZ-MDW
5/4Sat
multi-stopWestJet
15h 45mMDW-YYZ
$461
4/29Mon
multi-stopWestJet
5h 10mYYZ-MDW
5/4Sat
multi-stopWestJet
15h 45mMDW-YYZ
$462
4/30Tue
multi-stopWestJet
5h 10mYYZ-MDW
5/11Sat
multi-stopWestJet
7h 12mMDW-YYZ
$469
4/29Mon
multi-stopWestJet
5h 37mYYZ-MDW
5/11Sat
multi-stopWestJet
9h 49mMDW-YYZ
$478
4/27Sat
multi-stopWestJet
4h 37mYYZ-MDW
5/8Wed
multi-stopWestJet
5h 10mMDW-YYZ
$482
4/30Tue
multi-stop
15h 36mYYZ-MDW
5/6Mon
multi-stop
13h 25mMDW-YYZ
$486

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Toronto Pearson Airport - Chicago Midway Airport Flights

Departure:

Toronto Pearson Airport (YYZ)Canada

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Toronto Pearson Airport

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