HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$134+ Cheap flights from Pearson Intl (YYZ) to Midway (MDW)

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 1/2. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
Nov 5 — Nov 121
Wed 11/5
Wed 11/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pearson Intl to Midway 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 Pearson Intl to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Pearson Intl (YYZ) to Midway (MDW). 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 October 6, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$211
(Delta)

One-way from

$134
(Delta)

Popular in

September

Cheapest in

February

Average price

$513
Provider with most accurate pricing for Toronto Pearson Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toronto Pearson Intl-Chicago Midway flights.
Search Deals
From Toronto Pearson Intl to Chicago Midway
Search Deals
One-way flight from Toronto Pearson Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 32% potential increase in price ($160 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find flight deals from Pearson Intl to Midway

Cheapest flights from Pearson Intl to Midway
Explore the most affordable flight options available from Pearson Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 6, 2025.

This Bravofly deal was found by Cheapflights users on 10/5. 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 Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:00 pmYYZ - MDW
1 stop16h 45mWestJet
Mon 11/39:20 amMDW - YYZ
1 stop12h 58mWestJet
Deal found 10/5$238
This Kiwi.com deal was found by Cheapflights users on 10/5. 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.
Wed 10/295:15 pmYYZ - MDW
1 stop16h 57mMultiple Airlines
Mon 11/39:32 amMDW - YYZ
1 stop13h 39mMultiple Airlines
Deal found 10/5$246
This FlightHub deal was found by Cheapflights users on 10/4. 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.
Sat 11/16:20 amYYZ - MDW
1 stop5h 10mWestJet
Sat 11/89:20 amMDW - YYZ
1 stop5h 39mWestJet
Deal found 10/4$248
This Trip.com deal was found by Cheapflights users on 10/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/196:30 amYYZ - MDW
1 stop7h 37mWestJet
Wed 11/269:41 amMDW - YYZ
1 stop5h 21mWestJet
Deal found 10/5$250
This FlightHub deal was found by Cheapflights users on 10/3. 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.
Sat 11/86:20 amYYZ - MDW
1 stop5h 10mWestJet
Tue 11/119:41 amMDW - YYZ
1 stop5h 21mWestJet
Deal found 10/3$251
This FlightHub deal was found by Cheapflights users on 10/5. 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.
Sat 11/86:20 amYYZ - MDW
1 stop5h 10mWestJet
Sat 11/1510:47 amMDW - YYZ
1 stop5h 13mWestJet
Deal found 10/5$255
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 11/16:20 amYYZ - MDW
1 stop7h 48mWestJet
Mon 11/39:20 amMDW - YYZ
2 stops13h 19mWestJet
Deal found 10/4$265
This Delta deal was found by Cheapflights users on 10/4. 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.
Sat 11/16:15 amYYZ - MDW
1 stop3h 25mDelta
Mon 11/31:48 pmMDW - YYZ
1 stop8h 30mDelta
Deal found 10/4$266

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pearson Intl to Midway 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 October 6, 2025.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Pearson Intl

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 2/22

6:00 am-12:35 pm

1 stop7h 35m

Chicago Midway

Mon 2/23

2:00 pm-11:04 pm

1 stop8h 04m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 1/16

6:00 am-8:50 am

1 stop3h 50m

Chicago Midway

Mon 1/19

1:00 pm-7:09 pm

1 stop5h 09m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 3/24

6:00 am-12:35 pm

1 stop7h 35m

Chicago Midway

Wed 3/25

2:00 pm-11:04 pm

1 stop8h 04m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 2/9

7:45 am-12:35 pm

1 stop5h 50m

Chicago Midway

Thu 2/12

1:00 pm-7:09 pm

1 stop5h 09m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 1/11

6:00 am-8:50 am

1 stop3h 50m

Chicago Midway

Sun 1/18

5:59 pm-11:02 pm

1 stop4h 03m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/4

6:00 am-8:50 am

1 stop3h 50m

Chicago Midway

Tue 4/7

9:30 am-5:24 pm

1 stop6h 54m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 11/8

6:20 am-10:30 am

1 stop5h 10m

Chicago Midway

Sat 11/15

10:47 am-5:00 pm

1 stop5h 13m

$255

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 3/27

3:59 pm-6:34 pm

1 stop3h 35m

Chicago Midway

Mon 3/30

2:00 pm-11:04 pm

1 stop8h 04m

$264

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 1/2

9:54 am-5:26 pm

1 stop8h 32m

$134

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 10/30

5:15 pm-8:32 am

1 stop16h 17m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/3

Showing 1-10 of 17 results
1
2

Compare providers for flights from Pearson Intl to Midway

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

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

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

Currently, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of $129). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in October is currently the most expensive (average of $421). 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 Pearson Intl to Midway. 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 Toronto Pearson Intl Airport to Chicago Midway Airport?

    A quick flight from Toronto Pearson Intl Airport to Chicago Midway Airport can take about 7h 35m. Delta provides one of the quickest options available for as low as $211. There are 432 mi between Toronto Pearson Intl Airport and Chicago Midway Airport.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Pearson Intl to Midway 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 Toronto Pearson Intl Airport to Chicago Midway Airport?

    Currently, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of $129). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in October is currently the most expensive (average of $421). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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 Pearson Intl to Midway

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