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Cheap flights from Chicago Midway Airport to Toronto Pearson Intl Airport from C$ 129

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 18/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
26 Feb — 5 Mar1
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 27 January 2026.

Tue 17/26:20 p.m.
MDW
-
YYZ
1 stop3h 20m
Delta
Wed 25/210:05 a.m.
YYZ
-
MDW
1 stop3h 41m
Delta
Deal found 26/1C$ 338
Fri 13/32:05 p.m.
MDW
-
YYZ
1 stop8h 01m
Delta
Fri 20/312:15 p.m.
YYZ
-
MDW
1 stop6h 39m
Delta
Deal found 27/1C$ 340
Thu 19/29:50 a.m.
MDW
-
YYZ
1 stop5h 09m
Delta
Sun 22/212:11 p.m.
YYZ
-
MDW
1 stop6h 26m
Delta
Deal found 25/1C$ 341
Thu 19/29:34 a.m.
MDW
-
YYZ
1 stop5h 36m
Delta
Mon 23/212:11 p.m.
YYZ
-
MDW
1 stop6h 26m
Delta
Deal found 26/1C$ 351
Sun 15/29:34 a.m.
MDW
-
YYZ
1 stop5h 36m
Delta
Thu 26/26:10 a.m.
YYZ
-
MDW
1 stop3h 44m
Delta
Deal found 26/1C$ 382
Sat 14/21:29 p.m.
MDW
-
YYZ
1 stop4h 40m
Delta
Tue 17/210:05 a.m.
YYZ
-
MDW
1 stop3h 41m
Delta
Deal found 27/1C$ 383
Fri 22/59:30 a.m.
MDW
-
YYZ
1 stop6h 53m
Delta
Mon 25/56:00 a.m.
YYZ
-
MDW
1 stop7h 30m
Delta
Deal found 27/1C$ 385
Thu 12/29:34 a.m.
MDW
-
YYZ
1 stop5h 36m
Delta
Mon 16/210:05 a.m.
YYZ
-
MDW
1 stop8h 32m
Delta
Deal found 26/1C$ 386
Tue 10/311:19 a.m.
MDW
-
YYZ
1 stop11h 55m
Multiple Airlines
Mon 16/38:30 p.m.
YYZ
-
MDW
2 stops17h 32m
Multiple Airlines
Deal found 27/1C$ 408
Fri 13/21:29 p.m.
MDW
-
YYZ
1 stop8h 11m
Delta
Sun 15/27:45 a.m.
YYZ
-
MDW
1 stop6h 01m
Delta
Deal found 27/1C$ 427
Thu 4/69:30 a.m.
MDW
-
YYZ
1 stop6h 53m
Delta
Sun 7/66:00 a.m.
YYZ
-
MDW
1 stop7h 30m
Delta
Deal found 25/1C$ 430

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 27 January 2026.

Round-trip from

C$ 338

One-way from

C$ 129

Popular in

September

Cheapest in

November

Average price

C$ 468
Delta
  • Delta
  • 17/2-25/2
  • 2 total stops
  • 7h 01m total
  • Chicago to Toronto
Search Deals
Delta
  • Delta
  • 18/2
  • 1 total stop
  • 3h 20m total
  • Chicago to Toronto
Search Deals
Highest demand for flights based on searches. 28% potential increase in price (C$ 302 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease (C$ 90 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 27 January 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

Mon 6/4

1:10 p.m.-5:17 p.m.

1 stop3h 07m

Toronto Pearson Intl

Wed 15/4

2:15 p.m.-5:58 p.m.

1 stop4h 43m

C$ 338

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 28/3

9:35 a.m.-5:17 p.m.

1 stop6h 42m

Toronto Pearson Intl

Tue 31/3

6:30 a.m.-1:25 p.m.

1 stop7h 55m

C$ 338

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 13/3

6:34 p.m.-10:39 p.m.

1 stop3h 05m

Toronto Pearson Intl

Mon 16/3

6:20 a.m.-12:29 p.m.

1 stop7h 09m

C$ 338

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 23/2

6:17 p.m.-10:40 p.m.

1 stop3h 23m

Toronto Pearson Intl

Thu 5/3

6:10 a.m.-8:54 a.m.

1 stop3h 44m

C$ 338

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 31/3

9:30 a.m.-3:59 p.m.

1 stop5h 29m

Toronto Pearson Intl

Tue 7/4

10:05 a.m.-12:29 p.m.

1 stop3h 24m

C$ 338

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 21/2

1:28 p.m.-10:40 p.m.

1 stop8h 12m

Toronto Pearson Intl

Thu 5/3

6:10 a.m.-8:54 a.m.

1 stop3h 44m

C$ 338

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 16/2

1:26 p.m.-10:40 p.m.

1 stop8h 14m

Toronto Pearson Intl

Thu 26/2

6:30 a.m.-1:05 p.m.

1 stop7h 35m

C$ 338

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 17/2

6:20 p.m.-10:40 p.m.

1 stop3h 20m

Toronto Pearson Intl

Thu 19/2

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

1 stop6h 01m

C$ 338

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 16/4

9:27 a.m.-3:20 p.m.

1 stop4h 53m

Toronto Pearson Intl

Sun 19/4

6:10 a.m.-12:43 p.m.

1 stop7h 33m

C$ 338

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sun 22/2

1:28 p.m.-10:40 p.m.

1 stop8h 12m

Toronto Pearson Intl

Fri 6/3

6:10 a.m.-8:54 a.m.

1 stop3h 44m

C$ 338

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/1

Showing 1-10 of 22 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 22% of weekly flights between Chicago and Toronto have experienced delays in the past year, with the average delay time being 90 minutes.

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

Historically, flights departing in the morning 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?

Thursday 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 3h 07m. 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
Oakville
Collingwood
Kitchener
Markham
Vaughan
Barrie
Burlington
Richmond Hill
Milton
Cambridge
Muskoka
Waterloo
Oshawa
Guelph
Lindsay
Peterborough
Brantford
St. Catharines
Cobourg

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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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