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$151+ 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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
Mar 17 — Mar 241
Tue 3/17
Tue 3/24
1 adult, Economy
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Cheap 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 February 15, 2026.

This Delta deal was found by Cheapflights users on 2/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:29 pm
YYZ
-
MDW
1 stop6h 27m
Delta
Sun 5/316:36 pm
MDW
-
YYZ
1 stop3h 23m
Delta
Deal found 2/14$242
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:11 pm
YYZ
-
MDW
1 stop6h 26m
Delta
Wed 3/116:34 pm
MDW
-
YYZ
1 stop3h 05m
Delta
Deal found 2/12$243
This Delta deal was found by Cheapflights users on 2/11. 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.
Wed 3/47:45 am
YYZ
-
MDW
1 stop6h 01m
Delta
Sat 3/75:00 pm
MDW
-
YYZ
1 stop5h 11m
Delta
Deal found 2/11$244
This Delta deal was found by Cheapflights users on 2/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:30 am
YYZ
-
MDW
1 stop7h 55m
Delta
Mon 4/69:35 am
MDW
-
YYZ
1 stop6h 42m
Delta
Deal found 2/14$265
This Delta deal was found by Cheapflights users on 2/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/36:20 am
YYZ
-
MDW
1 stop3h 33m
Delta
Mon 4/69:35 am
MDW
-
YYZ
1 stop6h 42m
Delta
Deal found 2/13$266
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 7/89:45 am
YYZ
-
MDW
1 stop3h 45m
WestJet
Fri 7/105:59 pm
MDW
-
YYZ
1 stop3h 58m
WestJet
Deal found 2/11$280
This Delta deal was found by Cheapflights users on 2/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:45 am
YYZ
-
MDW
1 stop6h 01m
Delta
Thu 3/129:30 am
MDW
-
YYZ
1 stop5h 29m
Delta
Deal found 2/13$281
This Delta deal was found by Cheapflights users on 2/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:10 am
YYZ
-
MDW
1 stop3h 44m
Delta
Sat 3/75:00 pm
MDW
-
YYZ
1 stop5h 11m
Delta
Deal found 2/13$282
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:10 am
YYZ
-
MDW
1 stop3h 44m
Delta
Sat 3/75:00 pm
MDW
-
YYZ
1 stop5h 11m
Delta
Deal found 2/12$283
This Delta deal was found by Cheapflights users on 2/11. 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.
Mon 3/27:45 am
YYZ
-
MDW
1 stop6h 01m
Delta
Mon 3/99:35 am
MDW
-
YYZ
1 stop4h 33m
Delta
Deal found 2/11$287
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Mon 3/27:10 am
YYZ
-
MDW
2 stops36h 57m
Multiple Airlines
Mon 3/99:51 pm
MDW
-
YYZ
1 stop15h 17m
Multiple Airlines
Deal found 2/11$289
This CheapTicketsDeal deal was found by Cheapflights users on 2/15. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2210:05 am
YYZ
-
MDW
1 stop3h 24m
WestJet
Sun 3/299:35 am
MDW
-
YYZ
1 stop6h 42m
WestJet
Deal found 2/15$291

Find 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 February 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$242
(Delta)

One-way from

$151
(Delta)

Popular in

September

Cheapest in

December

Average price

$282
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. 25% potential increase in price ($107 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 15, 2026.
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

Wed 5/20

12:09 pm-6:14 pm

1 stop7h 05m

Chicago Midway

Wed 5/27

9:22 am-1:24 pm

1 stop3h 02m

$242

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 4/23

2:15 pm-5:58 pm

1 stop4h 43m

Chicago Midway

Mon 5/4

6:38 pm-10:56 pm

1 stop3h 18m

$242

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 5/22

12:09 pm-6:14 pm

1 stop7h 05m

Chicago Midway

Wed 5/27

9:22 am-1:24 pm

1 stop3h 02m

$242

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 5/29

2:14 pm-6:14 pm

1 stop5h 00m

Chicago Midway

Sun 5/31

6:36 pm-10:59 pm

1 stop3h 23m

$242

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 5/28

6:10 am-8:43 am

1 stop3h 33m

Chicago Midway

Sat 5/30

9:22 am-1:24 pm

1 stop3h 02m

$242

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 5/20

6:10 am-8:43 am

1 stop3h 33m

Chicago Midway

Fri 5/22

9:22 am-5:21 pm

1 stop6h 59m

$242

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 5/24

2:14 pm-6:14 pm

1 stop5h 00m

Chicago Midway

Sat 5/30

9:22 am-1:24 pm

1 stop3h 02m

$242

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 5/24

6:10 am-8:43 am

1 stop3h 33m

Chicago Midway

Tue 5/26

9:22 am-3:16 pm

1 stop4h 54m

$242

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 5/20

6:10 am-8:43 am

1 stop3h 33m

Chicago Midway

Sun 5/24

9:22 am-5:21 pm

1 stop6h 59m

$242

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 5/26

2:14 pm-6:14 pm

1 stop5h 00m

Chicago Midway

Fri 5/29

9:22 am-1:24 pm

1 stop3h 02m

$242

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/13

Showing 1-10 of 23 results
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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 February.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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

How often are flights from Toronto to Chicago delayed?

About 21% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 48 minutes.

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

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Monday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Toronto to Chicago flights?

Over the last year, Air Canada have had the lowest number of delays on this route, with just 50% of flights being delayed.

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 05m. Delta provides one of the quickest options available for as low as $242. 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.

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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Pearson Intl to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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