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Cheap flights from Chicago Midway Airport to Toronto Pearson Intl Airport from C$ 138

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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
28 May — 4 Jun1
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 28 April 2026.

Fri 29/51:59 p.m.
MDW
-
YYZ
1 stop8h 15m
Delta
Mon 1/612:09 p.m.
YYZ
-
MDW
1 stop7h 24m
Delta
Deal found 27/4C$ 354
Thu 7/59:22 a.m.
MDW
-
YYZ
1 stop3h 08m
Delta
Fri 12/612:09 p.m.
YYZ
-
MDW
1 stop7h 22m
Delta
Deal found 23/4C$ 356
Tue 23/69:17 a.m.
MDW
-
YYZ
1 stop3h 22m
Delta
Tue 30/612:09 p.m.
YYZ
-
MDW
1 stop7h 22m
Delta
Deal found 24/4C$ 383
Thu 11/61:49 p.m.
MDW
-
YYZ
1 stop8h 25m
Delta
Tue 16/66:10 a.m.
YYZ
-
MDW
1 stop4h 04m
Delta
Deal found 24/4C$ 390
Mon 13/79:20 a.m.
MDW
-
YYZ
1 stop5h 00m
Delta
Sat 18/712:09 p.m.
YYZ
-
MDW
1 stop6h 53m
Delta
Deal found 23/4C$ 410
Thu 25/69:17 a.m.
MDW
-
YYZ
1 stop7h 07m
Delta
Sun 28/66:05 a.m.
YYZ
-
MDW
1 stop7h 36m
Delta
Deal found 27/4C$ 418
Sat 13/66:35 p.m.
MDW
-
YYZ
1 stop3h 27m
Delta
Sat 27/66:05 a.m.
YYZ
-
MDW
1 stop7h 36m
Delta
Deal found 26/4C$ 421
Tue 15/99:20 a.m.
MDW
-
YYZ
1 stop8h 05m
Delta
Thu 17/912:15 p.m.
YYZ
-
MDW
1 stop7h 16m
Delta
Deal found 28/4C$ 423
Fri 29/59:22 a.m.
MDW
-
YYZ
1 stop6h 59m
KLM
Sun 31/512:09 p.m.
YYZ
-
MDW
1 stop7h 24m
KLM
Deal found 25/4C$ 425
Wed 3/66:36 p.m.
MDW
-
YYZ
1 stop3h 23m
Delta
Fri 5/612:29 p.m.
YYZ
-
MDW
1 stop6h 27m
Delta
Deal found 25/4C$ 433
Mon 8/69:17 a.m.
MDW
-
YYZ
1 stop7h 07m
Delta
Mon 15/612:09 p.m.
YYZ
-
MDW
1 stop7h 22m
Delta
Deal found 24/4C$ 435
Sun 24/51:59 p.m.
MDW
-
YYZ
1 stop8h 15m
Delta
Wed 27/59:49 a.m.
YYZ
-
MDW
1 stop3h 53m
Delta
Deal found 23/4C$ 436

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 28 April 2026.

Round-trip from

C$ 354

One-way from

C$ 138

Popular in

September

Cheapest in

July

Average price

C$ 339
Delta
  • Delta
  • 29/5-1/6
  • 2 total stops
  • 15h 39m total
  • Chicago to Toronto
Search Deals
Delta
  • Delta
  • 5/6
  • 1 total stop
  • 6h 59m total
  • Chicago to Toronto
Search Deals
Highest demand for flights based on searches. 29% potential increase in price (C$ 285 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease (C$ 78 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 28 April 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 11/6

1:21 p.m.-11:02 p.m.

1 stop8h 41m

Toronto Pearson Intl

Sun 14/6

2:29 p.m.-6:31 p.m.

1 stop5h 02m

C$ 354

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 30/5

6:36 p.m.-10:59 p.m.

1 stop3h 23m

Toronto Pearson Intl

Sun 31/5

6:30 a.m.-1:19 p.m.

1 stop7h 49m

C$ 354

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 29/5

9:22 a.m.-5:21 p.m.

1 stop6h 59m

Toronto Pearson Intl

Sun 31/5

6:10 a.m.-12:42 p.m.

1 stop7h 32m

C$ 354

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 13/6

9:17 a.m.-3:19 p.m.

1 stop5h 02m

Toronto Pearson Intl

Sat 20/6

6:05 a.m.-9:14 a.m.

1 stop4h 09m

C$ 354

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 12/6

1:21 p.m.-11:02 p.m.

1 stop8h 41m

Toronto Pearson Intl

Fri 19/6

12:09 p.m.-6:31 p.m.

1 stop7h 22m

C$ 354

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 19/6

9:17 a.m.-5:24 p.m.

1 stop7h 07m

Toronto Pearson Intl

Tue 23/6

12:09 p.m.-6:31 p.m.

1 stop7h 22m

C$ 354

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 26/5

9:22 a.m.-5:21 p.m.

1 stop6h 59m

Toronto Pearson Intl

Thu 28/5

12:09 p.m.-6:33 p.m.

1 stop7h 24m

C$ 354

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 28/5

9:23 a.m.-6:31 p.m.

1 stop8h 08m

Toronto Pearson Intl

Sun 31/5

6:30 a.m.-1:19 p.m.

1 stop7h 49m

C$ 356

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 29/5

1:59 p.m.-11:14 p.m.

1 stop8h 15m

Toronto Pearson Intl

Wed 3/6

9:49 a.m.-12:42 p.m.

1 stop3h 53m

C$ 356
Quickest round-trip

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 3/6

6:36 p.m.-10:59 p.m.

1 stop3h 23m

Toronto Pearson Intl

Sun 7/6

6:10 a.m.-9:14 a.m.

1 stop4h 04m

C$ 356

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/4

Showing 1-10 of 22 resultsSorted by cheapest first
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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

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

Currently, July is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto Pearson Intl Airport (average of C$ 288). Flying from Chicago Midway Airport to Toronto Pearson Intl Airport in September is currently the most expensive (average of C$ 1,123). 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 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 8h 41m. 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.

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

    Currently, July is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto Pearson Intl Airport (average of C$ 288). Flying from Chicago Midway Airport to Toronto Pearson Intl Airport in September is currently the most expensive (average of C$ 1,123). 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

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

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

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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