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Cheap flights from Chicago Midway Airport to Toronto Pearson Intl Airport from C$ 146

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 16/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Midway to Pearson Intl

Enter your travel dates to find the best prices.

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 12 December 2025.

Thu 25/126:08 p.m.MDW - YYZ
1 stop13h 50mWestJet
Thu 1/16:00 a.m.YYZ - MDW
1 stop6h 06mWestJet
Deal found 12/12C$ 517
Thu 25/127:44 a.m.MDW - YYZ
2 stops31h 34mMultiple Airlines
Thu 1/16:00 a.m.YYZ - MDW
1 stop6h 06mMultiple Airlines
Deal found 12/12C$ 521
Mon 15/123:52 p.m.MDW - YYZ
2 stops21h 13mMultiple Airlines
Thu 15/16:00 a.m.YYZ - MDW
1 stop3h 52mMultiple Airlines
Deal found 11/12C$ 554
Thu 11/122:16 p.m.MDW - YYZ
1 stop26h 14mMultiple Airlines
Wed 14/16:00 a.m.YYZ - MDW
1 stop3h 52mMultiple Airlines
Deal found 10/12C$ 557
Wed 31/129:50 a.m.MDW - YYZ
1 stop24h 18mWestJet
Tue 6/16:00 a.m.YYZ - MDW
1 stop3h 52mWestJet
Deal found 11/12C$ 587
Wed 24/129:50 a.m.MDW - YYZ
1 stop24h 18mWestJet
Thu 1/16:00 a.m.YYZ - MDW
1 stop6h 06mWestJet
Deal found 10/12C$ 610
Fri 26/126:08 p.m.MDW - YYZ
1 stop3h 42mWestJet
Thu 1/16:00 a.m.YYZ - MDW
1 stop6h 06mWestJet
Deal found 12/12C$ 623
Wed 31/129:50 a.m.MDW - YYZ
1 stop24h 18mWestJet
Wed 7/16:00 a.m.YYZ - MDW
1 stop7h 48mWestJet
Deal found 11/12C$ 634
Thu 18/129:34 a.m.MDW - YYZ
1 stop4h 14mWestJet
Mon 5/15:15 p.m.YYZ - MDW
1 stop20h 54mWestJet
Deal found 10/12C$ 656

Find 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 12 December 2025.

Round-trip from

C$ 321

One-way from

C$ 146

Popular in

February

Cheapest in

September

Average price

C$ 405
Delta
  • Delta
  • 5/2-8/2
  • 2 total stops
  • 8h 58m total
  • Chicago to Toronto
Search Deals
Delta
  • Delta
  • 16/1
  • 1 total stop
  • 3h 11m total
  • Chicago to Toronto
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 629,999 searches. Data last updated 12 December 2025.
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

Tue 10/2

1:26 p.m.-7:08 p.m.

1 stop4h 42m

Toronto Pearson Intl

Fri 13/2

10:05 a.m.-5:37 p.m.

1 stop8h 32m

C$ 321

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 5/2

9:33 a.m.-4:12 p.m.

1 stop5h 39m

Toronto Pearson Intl

Sun 8/2

6:00 a.m.-8:52 a.m.

1 stop3h 52m

C$ 321

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 5/2

9:53 a.m.-3:59 p.m.

1 stop5h 06m

Toronto Pearson Intl

Mon 9/2

7:45 a.m.-12:46 p.m.

1 stop6h 01m

C$ 321

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 17/2

1:28 p.m.-7:09 p.m.

1 stop4h 41m

Toronto Pearson Intl

Thu 19/2

6:15 a.m.-8:53 a.m.

1 stop3h 38m

C$ 321

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 6/2

1:26 p.m.-10:42 p.m.

1 stop8h 16m

Toronto Pearson Intl

Tue 10/2

7:45 a.m.-12:46 p.m.

1 stop6h 01m

C$ 321

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 29/1

1:26 p.m.-7:08 p.m.

1 stop4h 42m

Toronto Pearson Intl

Mon 2/2

10:05 a.m.-5:55 p.m.

1 stop8h 50m

C$ 346

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 29/1

9:50 a.m.-3:59 p.m.

1 stop5h 09m

Toronto Pearson Intl

Sun 1/2

6:30 a.m.-1:06 p.m.

1 stop7h 36m

C$ 346

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sun 25/1

1:26 p.m.-7:08 p.m.

1 stop4h 42m

Toronto Pearson Intl

Sun 1/2

12:12 p.m.-5:55 p.m.

1 stop6h 43m

C$ 346

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 30/1

1:49 p.m.-11:13 p.m.

1 stop8h 24m

C$ 146

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 22/1

9:32 a.m.-4:12 p.m.

1 stop5h 40m

C$ 146

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 19 results
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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 past year, Contour has 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?

    There are many flights that can get you from Chicago Midway Airport to Toronto Pearson Intl Airport in 4h 42m. Fly via Delta to get the fastest option. The distance between Chicago Midway Airport and Toronto Pearson Intl Airport is about 695 km.

  • 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

Travelling 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
Markham
Oakville
Collingwood
Vaughan
Kitchener
Burlington
Richmond Hill
Barrie
Milton
Muskoka
Cambridge
Waterloo
Guelph
Lindsay
Pickering
Peterborough
Oshawa
St. Catharines
Brantford

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Midway to Pearson Intl

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Pearson Intl flights
Midway to Toronto Island flights
O'Hare Intl to Toronto Island flights
O'Hare Intl to Hamilton flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Midway to Pearson Intl?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Midway to Pearson Intl. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Midway to Pearson Intl?

Millions of users choose and trust Cheapflights to book the best flight deals from Midway to Pearson Intl for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Midway to Pearson Intl with no change fees?

Need flexible booking options for your flight to Pearson Intl from Midway? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Midway to Pearson Intl become cheaper?

Yes! Start tracking prices for Midway to Pearson Intl flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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