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$128+ 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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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 November 20, 2025.

This Delta deal was found by Cheapflights users on 11/18. 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 12/116:05 amYYZ - MDW
1 stop7h 29mDelta
Tue 12/169:34 amMDW - YYZ
1 stop4h 14mDelta
Deal found 11/18$210
This Delta deal was found by Cheapflights users on 11/18. 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 12/116:05 amYYZ - MDW
1 stop3h 49mDelta
Mon 12/156:40 pmMDW - YYZ
1 stop3h 31mDelta
Deal found 11/18$222
This Delta deal was found by Cheapflights users on 11/19. 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.
Sun 12/76:05 amYYZ - MDW
1 stop3h 49mDelta
Sat 12/136:46 pmMDW - YYZ
1 stop3h 25mDelta
Deal found 11/19$223
This Delta deal was found by Cheapflights users on 11/19. 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.
Fri 12/53:38 pmYYZ - MDW
1 stop3h 22mDelta
Sun 12/76:40 pmMDW - YYZ
1 stop3h 31mDelta
Deal found 11/19$234
This Delta deal was found by Cheapflights users on 11/19. 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.
Fri 12/266:00 amYYZ - MDW
1 stop6h 06mDelta
Tue 1/66:14 pmMDW - YYZ
1 stop3h 27mDelta
Deal found 11/19$240
This Delta deal was found by Cheapflights users on 11/18. 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 12/116:05 amYYZ - MDW
1 stop3h 49mDelta
Sun 12/149:34 amMDW - YYZ
1 stop6h 41mDelta
Deal found 11/18$260
This Delta deal was found by Cheapflights users on 11/20. 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 12/266:00 amYYZ - MDW
1 stop6h 06mDelta
Mon 1/51:28 pmMDW - YYZ
1 stop8h 13mDelta
Deal found 11/20$267
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Thu 12/186:12 pmYYZ - MDW
1 stop16h 42mWestJet
Thu 12/259:50 amMDW - YYZ
1 stop13h 09mWestJet
Deal found 11/20$272
This FlightHub deal was found by Cheapflights users on 11/20. 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.
Mon 12/155:15 pmYYZ - MDW
1 stop20h 55mWestJet
Fri 12/1910:49 amMDW - YYZ
1 stop5h 13mWestJet
Deal found 11/20$278
This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
Tue 12/96:30 pmYYZ - MDW
2 stops16h 24mWestJet
Sat 12/1311:05 amMDW - YYZ
1 stop4h 57mWestJet
Deal found 11/18$283

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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$201
(Delta)

One-way from

$128
(Delta)

Popular in

September

Cheapest in

November

Average price

$217
Provider with most accurate pricing for Toronto Pearson Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toronto Pearson Intl-Chicago Midway flights.
Search Deals
From Toronto Pearson Intl to Chicago Midway
Search Deals
One-way flight from Toronto Pearson Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 31% potential increase in price ($141 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 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 1/8

10:05 am-12:48 pm

1 stop3h 43m

Chicago Midway

Sun 1/11

6:30 pm-10:41 pm

1 stop3h 11m

$201

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 4/23

12:15 pm-6:31 pm

1 stop7h 16m

Chicago Midway

Mon 5/4

9:30 am-5:23 pm

1 stop6h 53m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 1/25

6:00 am-12:46 pm

1 stop7h 46m

Chicago Midway

Thu 1/29

1:26 pm-7:08 pm

1 stop4h 42m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 2/15

6:15 am-8:54 am

1 stop3h 39m

Chicago Midway

Tue 2/17

1:28 pm-7:08 pm

1 stop4h 40m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 2/27

6:15 am-8:54 am

1 stop3h 39m

Chicago Midway

Mon 3/2

9:34 am-7:08 pm

1 stop8h 34m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/5

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Sat 2/7

1:26 pm-10:42 pm

1 stop8h 16m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 3/19

6:00 am-8:50 am

1 stop3h 50m

Chicago Midway

Mon 3/23

5:59 pm-11:02 pm

1 stop4h 03m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 2/27

10:05 am-5:37 pm

1 stop8h 32m

Chicago Midway

Sun 3/1

1:49 pm-11:13 pm

1 stop8h 24m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 1/1

6:05 am-8:49 am

1 stop3h 44m

$128

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 12/11

6:05 am-12:34 pm

1 stop7h 29m

$128

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 19 results
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Compare providers for flights from Pearson Intl to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pearson Intl to Midway in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Toronto Pearson Intl Airport-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Toronto Pearson Intl Airport-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Toronto Pearson Intl Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto Pearson Intl Airport-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Toronto Pearson Intl Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of $129). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in October is currently the most expensive (average of $345). 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 3h 43m. Delta provides one of the quickest options available for as low as $201. 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, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of $129). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in October is currently the most expensive (average of $345). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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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