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YYZ - MDW

$148 Find cheap flights from Toronto Pearson Airport to Chicago Midway 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 Pearson Intl to Midway departing on 6/12. 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
sáb. 6/29
sáb. 7/6

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 42,686,544 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.

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

 
These are the cheapest deals for flights from Pearson Intl to Midway 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 Pearson Intl to Midway

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

Recent one-way flight deals from Pearson Intl to Midway

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

Recent last minute flight deals from Pearson Intl to Midway

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

Recent direct flight deals from Pearson Intl to Midway

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

Cheap bus & train deals from Pearson Intl to Midway

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

All round-trip flight deals to Midway

The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
12:30 pm - 5:04 pmYYZ-MDW
5h 34m1 stop
9:29 am - 6:33 pmMDW-YYZ
8h 04m1 stop
$241Delta
Find Deal
mar., jun. 18 - mar., jun. 25
12:30 pm - 5:04 pmYYZ-MDW
5h 34m1 stop
9:29 am - 6:33 pmMDW-YYZ
8h 04m1 stop
$242Delta
Find Deal
mar., jun. 18 - mar., jun. 25
12:30 pm - 5:04 pmYYZ-MDW
5h 34m1 stop
5:45 pm - 10:53 pmMDW-YYZ
4h 08m1 stop
$249Delta
Find Deal
mar., jul. 16 - sáb., jul. 20
12:30 pm - 6:05 pmYYZ-MDW
6h 35m1 stop
9:35 am - 5:09 pmMDW-YYZ
6h 34m1 stop
$256Delta
Find Deal
sáb., sep. 28 - mié., oct. 9
12:31 pm - 6:36 pmYYZ-MDW
7h 05m1 stop
5:45 pm - 10:50 pmMDW-YYZ
4h 05m1 stop
$257Delta
Find Deal
mar., jun. 25 - sáb., jun. 29
12:30 pm - 5:03 pmYYZ-MDW
5h 33m1 stop
9:35 am - 5:09 pmMDW-YYZ
6h 34m1 stop
$260Delta
Find Deal
mar., oct. 1 - mié., oct. 9
10:35 am - 5:15 pmYYZ-MDW
7h 40m1 stop
7:54 pm - 6:45 amMDW-YYZ
9h 51m1 stop
$312
Find Deal
vie., jun. 14 - mar., jun. 18
6:15 am - 11:44 amYYZ-MDW
6h 29m1 stop
3:45 pm - 9:58 pmMDW-YYZ
5h 13m1 stop
$314WestJet
Find Deal
sáb., ago. 10 - mar., ago. 13
7:46 am - 11:55 amYYZ-MDW
5h 09m1 stop
3:45 pm - 9:59 pmMDW-YYZ
5h 14m1 stop
$317WestJet
Find Deal
dom., jun. 16 - mar., jun. 18
6:15 am - 11:44 amYYZ-MDW
6h 29m1 stop
12:35 pm - 10:20 amMDW-YYZ
20h 45m1 stop
$318WestJet
Find Deal
mar., ago. 27 - sáb., ago. 31
6:04 am - 8:48 amYYZ-MDW
3h 44m1 stop
$148Delta
Find Deal
mié., jun. 12
12:30 pm - 6:38 pmYYZ-MDW
7h 08m1 stop
$152Delta
Find Deal
mar., ago. 27
10:35 am - 5:15 pmYYZ-MDW
7h 40m1 stop
$167
Find Deal
vie., jun. 14
12:30 pm - 6:39 pmYYZ-MDW
7h 09m1 stop
$171Delta
Find Deal
mar., jul. 30
6:04 am - 12:42 pmYYZ-MDW
7h 38m1 stop
$172Delta
Find Deal
mar., ago. 6
12:30 pm - 6:38 pmYYZ-MDW
7h 08m1 stop
$176WestJet
Find Deal
sáb., ago. 31
10:35 am - 9:31 amYYZ-MDW
23h 56m1 stop
$177
Find Deal
mié., jun. 5
12:30 pm - 6:39 pmYYZ-MDW
7h 09m1 stop
$178WestJet
Find Deal
mar., jul. 9
12:31 pm - 6:36 pmYYZ-MDW
7h 05m1 stop
$179Delta
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lun., jun. 17
7:00 pm - 9:38 amYYZ-MDW
15h 38m2 stops
$180WestJet
Find Deal
sáb., ago. 31
6:04 am - 9:06 amYYZ-MDW
4h 02m1 stop
9:32 am - 5:09 pmMDW-YYZ
6h 37m1 stop
$340Delta
Find Deal
mar., jun. 4 - mié., jun. 5
12:30 pm - 6:07 pmYYZ-MDW
6h 37m1 stop
2:24 pm - 11:12 pmMDW-YYZ
7h 48m1 stop
$400Delta
Find Deal
mar., jun. 4 - mar., jun. 11
6:04 am - 9:06 amYYZ-MDW
4h 02m1 stop
9:46 am - 6:20 pmMDW-YYZ
7h 34m1 stop
$432Delta
Find Deal
dom., jun. 2 - mar., jun. 4
9:45 am - 5:06 pmYYZ-MDW
8h 21m1 stop
2:15 pm - 11:14 pmMDW-YYZ
7h 59m1 stop
$433Delta
Find Deal
vie., may. 31 - mié., jun. 5
12:30 pm - 5:06 pmYYZ-MDW
5h 36m1 stop
9:46 am - 6:20 pmMDW-YYZ
7h 34m1 stop
$434Delta
Find Deal
dom., jun. 2 - mar., jun. 4
6:04 am - 8:51 amYYZ-MDW
3h 47m1 stop
1:21 pm - 10:46 pmMDW-YYZ
8h 25m1 stop
$457Delta
Find Deal
sáb., jun. 1 - dom., jun. 2
6:17 am - 11:52 amYYZ-MDW
6h 35m1 stop
8:58 pm - 10:47 pmMDW-YYZ
24h 49m1 stop
$460
Find Deal
dom., jun. 2 - lun., jun. 10
7:45 am - 11:52 amYYZ-MDW
5h 07m1 stop
2:24 pm - 11:38 amMDW-YYZ
20h 14m1 stop
$464WestJet
Find Deal
dom., jun. 2 - lun., jun. 10
6:34 am - 1:35 pmYYZ-MDW
8h 01m1 stop
6:00 am - 12:10 pmMDW-YYZ
5h 10m1 stop
$465WestJet
Find Deal
lun., jun. 3 - mié., jun. 5
6:17 am - 11:52 amYYZ-MDW
6h 35m1 stop
2:15 pm - 11:14 pmMDW-YYZ
7h 59m1 stop
$466WestJet
Find Deal
dom., jun. 2 - mar., jun. 4

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 $371 and $338 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 50 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 ($148) and WestJet ($176), and the lowest round-trip tickets were found on Delta ($241) and WestJet ($314).

Good to know

Low season

January

High season

May

Cheapest flight

$148
Best time to beat the crowds with an average 37% 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 $148 for a one-way ticket and $241 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.
6/12mié.
1 stopDelta
3h 44mYYZ-MDW
$148
8/27mar.
1 stopDelta
7h 08mYYZ-MDW
$152
6/14vie.
1 stop
7h 40mYYZ-MDW
$167
7/30mar.
1 stopDelta
7h 09mYYZ-MDW
$171
8/6mar.
1 stopDelta
7h 38mYYZ-MDW
$172
8/31sáb.
1 stopWestJet
7h 08mYYZ-MDW
$176
6/5mié.
1 stop
23h 56mYYZ-MDW
$177
7/9mar.
1 stopWestJet
7h 09mYYZ-MDW
$178
6/17lun.
1 stopDelta
7h 05mYYZ-MDW
$179
8/31sáb.
2 stopsWestJet
15h 38mYYZ-MDW
$180

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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.
6/4mar.
multi-stopDelta
4h 02mYYZ-MDW
6/5mié.
multi-stopDelta
6h 37mMDW-YYZ
$340
6/4mar.
multi-stopDelta
6h 37mYYZ-MDW
6/11mar.
multi-stopDelta
7h 48mMDW-YYZ
$400
6/2dom.
multi-stopDelta
4h 02mYYZ-MDW
6/4mar.
multi-stopDelta
7h 34mMDW-YYZ
$432
5/31vie.
multi-stopDelta
8h 21mYYZ-MDW
6/5mié.
multi-stopDelta
7h 59mMDW-YYZ
$433
6/2dom.
multi-stopDelta
5h 36mYYZ-MDW
6/4mar.
multi-stopDelta
7h 34mMDW-YYZ
$434
6/1sáb.
multi-stopDelta
3h 47mYYZ-MDW
6/2dom.
multi-stopDelta
8h 25mMDW-YYZ
$457
6/2dom.
multi-stop
6h 35mYYZ-MDW
6/10lun.
multi-stop
24h 49mMDW-YYZ
$460
6/2dom.
multi-stopWestJet
5h 07mYYZ-MDW
6/10lun.
multi-stopWestJet
20h 14mMDW-YYZ
$464
6/3lun.
multi-stopWestJet
8h 01mYYZ-MDW
6/5mié.
multi-stopWestJet
5h 10mMDW-YYZ
$465
6/2dom.
multi-stopWestJet
6h 35mYYZ-MDW
6/4mar.
multi-stopWestJet
7h 59mMDW-YYZ
$466

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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

Cabin classes:

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