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Pearson Intl

$89+ Cheap flights from Midway (MDW) to Pearson Intl (YYZ)

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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheap flight deals from Midway to Pearson Intl

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Pearson Intl (YYZ). 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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$237
(Delta)

One-way from

$89
(Delta)

Popular in

December

Cheapest in

September

Average price

$255
Provider with most accurate pricing for Chicago Midway-Toronto Pearson Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Toronto Pearson Intl flights.
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From Chicago Midway to Toronto Pearson Intl
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One-way flight from Chicago Midway to Toronto Pearson Intl
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Highest demand for flights based on searches. 5% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Midway to Pearson Intl

Cheapest flights from Midway to Pearson Intl
Explore the most affordable flight options available from Midway to Pearson Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 8, 2026.

This Delta deal was found by Cheapflights users on 1/7. 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 2/51:26 pmMDW - YYZ
1 stop8h 16mDelta
Sun 2/86:00 amYYZ - MDW
1 stop3h 52mDelta
Deal found 1/7$237
This Delta deal was found by Cheapflights users on 1/7. 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 1/291:26 pmMDW - YYZ
1 stop8h 16mDelta
Mon 2/27:45 amYYZ - MDW
1 stop6h 01mDelta
Deal found 1/7$260
This Delta deal was found by Cheapflights users on 1/7. 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 3/139:30 amMDW - YYZ
1 stop5h 29mDelta
Sun 3/156:20 amYYZ - MDW
1 stop7h 09mDelta
Deal found 1/7$284
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Mon 2/91:00 pmMDW - YYZ
1 stop10h 14mMultiple Airlines
Wed 2/115:15 pmYYZ - MDW
1 stop16h 39mMultiple Airlines
Deal found 1/7$285
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Sun 2/11:00 pmMDW - YYZ
1 stop21h 26mMultiple Airlines
Sat 2/1412:20 pmYYZ - MDW
1 stop22h 46mMultiple Airlines
Deal found 1/6$289
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/171:28 pmMDW - YYZ
1 stop4h 41mMultiple Airlines
Wed 2/188:20 pmYYZ - MDW
1 stop19h 06mMultiple Airlines
Deal found 1/7$301
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Sat 1/319:33 amMDW - YYZ
1 stop5h 39mWestJet
Sun 2/15:15 pmYYZ - MDW
1 stop20h 31mWestJet
Deal found 1/7$306
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Sat 1/319:33 amMDW - YYZ
1 stop5h 39mWestJet
Tue 2/36:30 pmYYZ - MDW
2 stops16h 23mWestJet
Deal found 1/6$307
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Sat 3/141:10 pmMDW - YYZ
1 stop3h 07mWestJet
Fri 3/206:20 amYYZ - MDW
1 stop3h 33mWestJet
Deal found 1/6$311
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 2/191:26 pmMDW - YYZ
1 stop18h 36mWestJet
Sun 2/226:15 amYYZ - MDW
1 stop3h 39mWestJet
Deal found 1/6$312

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Pearson Intl 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 January 8, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Toronto Pearson Intl Airport that are best for you.

Fly from

Midway

Fly to

Pearson Intl

Route

Depart

Return

Price

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 2/5

1:26 pm-10:42 pm

1 stop8h 16m

Toronto Pearson Intl

Sun 2/8

6:30 am-11:05 am

1 stop5h 35m

$237

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 2/17

9:50 am-3:59 pm

1 stop5h 09m

Toronto Pearson Intl

Tue 2/24

6:30 am-1:05 pm

1 stop7h 35m

$237

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 2/12

9:34 am-4:10 pm

1 stop5h 36m

Toronto Pearson Intl

Mon 2/16

7:45 am-12:46 pm

1 stop6h 01m

$237

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 2/6

6:35 pm-10:42 pm

1 stop3h 07m

Toronto Pearson Intl

Sun 2/8

6:00 am-12:46 pm

1 stop7h 46m

$237

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 2/21

5:00 pm-11:11 pm

1 stop5h 11m

Toronto Pearson Intl

Wed 2/25

7:45 am-12:46 pm

1 stop6h 01m

$237

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 2/3

6:35 pm-10:42 pm

1 stop3h 07m

Toronto Pearson Intl

Thu 2/5

6:00 am-12:46 pm

1 stop7h 46m

$237

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sun 2/1

9:33 am-4:12 pm

1 stop5h 39m

Toronto Pearson Intl

Fri 2/27

12:11 pm-5:37 pm

1 stop6h 26m

$237

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 2/13

9:34 am-4:10 pm

1 stop5h 36m

Toronto Pearson Intl

Mon 2/16

7:45 am-12:46 pm

1 stop6h 01m

$237

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 2/12

9:34 am-4:10 pm

1 stop5h 36m

Toronto Pearson Intl

Sun 2/15

7:45 am-12:46 pm

1 stop6h 01m

$237

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sun 2/22

9:34 am-4:10 pm

1 stop5h 36m

$89

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

Showing 1-10 of 20 results
1
2

Compare providers for flights from Midway to Pearson Intl

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 Midway to Pearson Intl in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 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 Chicago Midway Airport-Toronto Pearson Intl Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Toronto Pearson Intl Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Toronto Pearson Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Toronto Pearson Intl 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 Chicago Midway Airport-Toronto Pearson Intl 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 Midway to Pearson Intl

Have a flexible travel schedule? Discover the best time to fly to Pearson Intl from Midway 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 Chicago Midway Airport to Toronto Pearson Intl Airport

How often are flights from Chicago to Toronto delayed?

About 25% of weekly flights between Chicago and Toronto have experienced delays in the past year, with the average delay time being 105 minutes.

What is the most punctual flight time for Chicago to Toronto flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Toronto flights?

Over the last year, Contour have had the lowest number of delays on this route, with just 25% of flights being delayed.

Related info for your journey

Find useful and relevant information for your journey from Midway to Pearson Intl. 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 Chicago Midway Airport to Toronto Pearson Intl Airport?

    Departing from Chicago Midway Airport to Toronto Pearson Intl Airport will take you 8h 16m. The distance from Chicago Midway Airport to Toronto Pearson Intl Airport is about 432 mi.

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

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

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

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

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

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

See more FAQs

Traveling to a place near Toronto Pearson Intl Airport?

Book flights to Toronto Pearson Intl Airport if you plan to visit one of these locations
Brampton
Kitchener
Markham
Collingwood
Oakville
Brantford
Pickering
Lindsay
Peterborough
Barrie
Cambridge
Milton
Oshawa
Burlington
Owen Sound
Ajax
Orillia
Vaughan
Richmond Hill
Gravenhurst

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