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$134+ Cheap flights from Pearson Intl (YYZ) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Pearson Intl to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Pearson Intl (YYZ) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 20, 2025.

Round-trip from

$212
(Delta)

One-way from

$134
(Delta)

Popular in

August

Cheapest in

February

Average price

$397
From Toronto Pearson Intl to Chicago Midway
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One-way flight from Toronto Pearson Intl to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Pearson Intl to Midway

Cheapest flights from Pearson Intl to Midway
Explore the most affordable flight options available from Pearson Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/712:15 pmYYZ - MDW
1 stop7h 10mDelta
Sun 10/129:35 amMDW - YYZ
1 stop4h 10mDelta
Deal found 8/18$212
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2312:30 pmYYZ - MDW
1 stop6h 05mDelta
Wed 10/19:35 amMDW - YYZ
1 stop4h 47mDelta
Deal found 8/17$224
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2612:15 pmYYZ - MDW
1 stop7h 20mDelta
Tue 9/309:35 amMDW - YYZ
1 stop6h 48mDelta
Deal found 8/18$236
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/236:30 amYYZ - MDW
1 stop6h 58mDelta
Thu 10/29:35 amMDW - YYZ
1 stop6h 48mDelta
Deal found 8/19$237
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/612:15 pmYYZ - MDW
1 stop7h 10mDelta
Sun 10/129:35 amMDW - YYZ
1 stop4h 10mDelta
Deal found 8/18$247
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2512:15 pmYYZ - MDW
1 stop7h 20mDelta
Mon 9/299:35 amMDW - YYZ
1 stop6h 48mDelta
Deal found 8/18$259
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/167:45 amYYZ - MDW
1 stop14h 51mWestJet
Tue 9/239:20 amMDW - YYZ
2 stops14h 11mWestJet
Deal found 8/19$265
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/11:20 pmYYZ - MDW
1 stop9h 16mWestJet
Fri 10/37:15 pmMDW - YYZ
2 stops21h 48mWestJet
Deal found 8/18$266
This FlightHub deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1712:37 pmYYZ - MDW
1 stop25h 31mWestJet
Tue 10/219:20 amMDW - YYZ
1 stop8h 10mWestJet
Deal found 8/18$270

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pearson Intl to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 20, 2025.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Pearson Intl

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 10/16

6:15 am-12:28 pm

1 stop7h 13m

Chicago Midway

Sat 10/18

6:23 pm-10:55 pm

1 stop3h 32m

$212

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 10/18

6:20 am-10:30 am

1 stop5h 10m

Chicago Midway

Tue 10/21

9:35 am-2:45 pm

1 stop4h 10m

$212

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 10/24

12:15 pm-6:25 pm

1 stop7h 10m

Chicago Midway

Mon 10/27

9:35 am-5:19 pm

1 stop6h 44m

$212

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 10/23

6:15 am-12:28 pm

1 stop7h 13m

Chicago Midway

Tue 10/28

9:35 am-5:19 pm

1 stop6h 44m

$212

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 10/8

12:15 pm-6:25 pm

1 stop7h 10m

Chicago Midway

Sun 10/12

9:35 am-2:45 pm

1 stop4h 10m

$212

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 10/7

12:15 pm-6:25 pm

1 stop7h 10m

Chicago Midway

Sun 10/12

9:35 am-2:45 pm

1 stop4h 10m

$212

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 10/7

12:15 pm-6:25 pm

1 stop7h 10m

Chicago Midway

Sat 10/11

3:00 pm-11:18 pm

1 stop7h 18m

$212

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 10/29

6:15 am-12:28 pm

1 stop7h 13m

Chicago Midway

Sat 11/1

6:35 pm-10:55 pm

1 stop3h 20m

$212

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 9/26

12:15 pm-6:35 pm

1 stop7h 20m

Chicago Midway

Thu 10/2

9:35 am-3:22 pm

1 stop4h 47m

$224

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 9/23

4:12 pm-6:35 pm

1 stop3h 23m

Chicago Midway

Thu 10/2

9:35 am-5:23 pm

1 stop6h 48m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 19 results
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Best time to book a flight from Pearson Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Pearson Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Toronto Pearson Intl Airport to Chicago Midway Airport

What is the cheapest month to book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of $160). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Pearson Intl to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Toronto Pearson Intl Airport to Chicago Midway Airport?

    A quick flight from Toronto Pearson Intl Airport to Chicago Midway Airport can take about 7h 13m. Delta provides one of the quickest options available for as low as $212. There are 432 mi between Toronto Pearson Intl Airport and Chicago Midway Airport.

  • Can I find deals for flights from Pearson Intl to Midway that include hotel bookings?

    Yes. In addition to deals on Pearson Intl to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pearson Intl to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pearson Intl to Midway.

  • Can I find deals for business class flights from Pearson Intl to Midway?

    Yes. Cheapflights offers flight deals from Pearson Intl to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, April is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of $160). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Pearson Intl to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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