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$135+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
Jul 16 — Jul 231
Wed 7/16
Wed 7/23
1 adult, Economy
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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 July 11, 2025.

Round-trip from

$213
(Delta)

One-way from

$135
(Delta)

Popular in

August

Cheapest in

February

Average price

$371
From Toronto Pearson Intl to Chicago Midway
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One-way flight from Toronto Pearson Intl to Chicago Midway
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Highest demand for flights based on searches. 17% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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 July 11, 2025.

This Delta deal was found by Cheapflights users on 7/10. 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 9/2010:12 amYYZ - MDW
1 stop3h 16mDelta
Tue 9/236:15 pmMDW - YYZ
1 stop3h 41mDelta
Deal found 7/10$213
This Kissandfly.com deal was found by Cheapflights users on 7/10. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1512:14 pmYYZ - MDW
1 stop7h 23mKLM
Sun 8/179:31 amMDW - YYZ
1 stop6h 52mKLM
Deal found 7/10$250
This oojo deal was found by Cheapflights users on 7/10. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/128:00 pmYYZ - MDW
2 stops14h 36mWestJet
Mon 8/189:15 amMDW - YYZ
2 stops14h 09mWestJet
Deal found 7/10$257

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 July 11, 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

Sat 9/20

10:12 am-12:28 pm

1 stop3h 16m

Chicago Midway

Tue 9/23

6:15 pm-10:56 pm

1 stop3h 41m

$213

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 8/15

12:14 pm-6:37 pm

1 stop7h 23m

Chicago Midway

Sun 8/17

9:31 am-5:23 pm

1 stop6h 52m

$250

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 8/12

8:00 pm-9:36 am

2 stops14h 36m

Chicago Midway

Mon 8/18

9:15 am-12:24 am

2 stops14h 09m

$257

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 9/1

12:14 pm-6:37 pm

1 stop7h 23m

$135

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 8/23

1:20 pm-9:12 pm

1 stop8h 52m

$152

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 8/17

7:45 am-10:24 pm

1 stop15h 39m

$190

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

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, April is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of $160). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

How much does it cost to fly round-trip from Toronto Pearson Intl Airport to Chicago Midway Airport?

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated July 11, 2025.
See what other customers who have flown with Delta, KLM, and WestJet from Toronto Pearson Intl Airport to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,951 reviews

Crew

8.5

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,951 reviews
Delta
8.0
Very good
7,951 reviews

Crew

8.5

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
KLM
7.8
Good
1,372 reviews
Delta
8.0
Very good
7,951 reviews

Crew

8.5

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
WestJet
7.2
Good
2,924 reviews
Delta
8.0
Very good
7,951 reviews

Crew

8.5

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

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.

  • What are the cheapest airlines flying from Toronto Pearson Intl Airport to Chicago Midway Airport round-trip?

    Delta, at $213, was found to be the cheapest airline from Toronto Pearson Intl Airport to Chicago Midway Airport.Alternate airlines to your destination round-trip include KLM and WestJet. Delta is 31% cheaper than the average price of flights available within the next 90 days to this destination.

  • 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, April is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of $160). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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