HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Pearson Intl

$109+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Pearson Intl with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 15, 2025.

Round-trip from

$269
(Kiwi.com)

One-way from

$109
(Kiwi.com)

Popular in

November

Cheapest in

July

Average price

$258
From Chicago Midway to Toronto Pearson Intl
Search Deals
One-way flight from Chicago Midway to Toronto Pearson Intl
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/319:32 amMDW - YYZ
1 stop9h 28mMultiple Airlines
Sun 11/28:00 pmYYZ - MDW
1 stop13h 32mMultiple Airlines
Deal found 9/15$269
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 11/1610:12 amMDW - YYZ
1 stop24h 34mMultiple Airlines
Sat 11/226:10 pmYYZ - MDW
1 stop16h 42mMultiple Airlines
Deal found 9/13$285
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Fri 11/143:27 pmMDW - YYZ
1 stop7h 44mMultiple Airlines
Sun 11/162:20 pmYYZ - MDW
1 stop11h 10mMultiple Airlines
Deal found 9/13$286
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Fri 10/36:21 amMDW - YYZ
1 stop14h 00mMultiple Airlines
Sun 10/58:00 pmYYZ - MDW
1 stop12h 23mMultiple Airlines
Deal found 9/13$287
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/1611:49 amMDW - YYZ
1 stop9h 51mMultiple Airlines
Sun 10/196:00 pmYYZ - MDW
1 stop5h 14mMultiple Airlines
Deal found 9/14$288
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/1110:35 amMDW - YYZ
1 stop5h 15mWestJet
Sun 10/126:00 pmYYZ - MDW
1 stop5h 14mWestJet
Deal found 9/12$292
This WestJet deal was found by Cheapflights users on 9/13. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/229:41 amMDW - YYZ
1 stop5h 21mWestJet
Sat 11/226:10 pmYYZ - MDW
1 stop16h 42mWestJet
Deal found 9/13$295
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Fri 10/179:45 amMDW - YYZ
1 stop10h 36mMultiple Airlines
Mon 10/206:00 pmYYZ - MDW
1 stop5h 14mMultiple Airlines
Deal found 9/13$297
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Fri 10/179:45 amMDW - YYZ
1 stop10h 36mMultiple Airlines
Sun 10/196:00 pmYYZ - MDW
1 stop5h 14mMultiple Airlines
Deal found 9/13$300
This FlightHub deal was found by Cheapflights users on 9/14. 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 10/69:20 amMDW - YYZ
1 stop12h 58mWestJet
Tue 10/147:45 amYYZ - MDW
1 stop15h 29mWestJet
Deal found 9/14$302

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 September 15, 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

Fri 10/31

9:32 am-8:00 pm

1 stop9h 28m

Toronto Pearson Intl

Sun 11/2

8:00 pm-8:32 am

1 stop13h 32m

$269

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sun 11/16

10:12 am-11:46 am

1 stop24h 34m

Toronto Pearson Intl

Sat 11/22

6:30 pm-9:52 am

2 stops16h 22m

$286

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 11/22

9:41 am-4:02 pm

1 stop5h 21m

Toronto Pearson Intl

Sat 11/22

6:10 pm-9:52 am

1 stop16h 42m

$295

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 10/17

6:24 pm-2:25 pm

2 stops19h 01m

Toronto Pearson Intl

Sun 10/19

6:00 pm-10:14 pm

1 stop5h 14m

$311

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 10/24

9:00 am-9:21 pm

2 stops11h 21m

Toronto Pearson Intl

Mon 10/27

6:00 pm-9:40 am

1 stop16h 40m

$312

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 10/29

9:20 am-11:18 pm

1 stop12h 58m

Toronto Pearson Intl

Sat 11/1

6:00 pm-10:45 am

1 stop17h 45m

$330

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 10/11

10:35 am-4:50 pm

1 stop5h 15m

Toronto Pearson Intl

Tue 10/14

7:45 am-10:14 pm

1 stop15h 29m

$330

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 12/17

10:49 am-11:59 pm

1 stop12h 10m

Toronto Pearson Intl

Tue 1/6

6:30 am-1:08 pm

1 stop7h 38m

$330

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 11/18

10:47 am-5:00 pm

1 stop5h 13m

Toronto Pearson Intl

Tue 11/25

6:30 am-1:07 pm

1 stop7h 37m

$330

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 10/11

10:35 am-9:55 pm

1 stop10h 20m

Toronto Pearson Intl

Wed 1/7

6:30 am-1:08 pm

1 stop7h 38m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 23 results
1
2
3

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.

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 5h 21m. 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.

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto Pearson Intl Airport (average of $243). Flying from Chicago Midway Airport to Toronto Pearson Intl Airport in August is currently the most expensive (average of $348). 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 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
Vaughan
Richmond Hill
Gravenhurst
St. Catharines

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

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.