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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 184

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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
8 jul. — 15 jul.1
1 adult

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 3 julio 2025.

Round-trip from

C$ 292

One-way from

C$ 184

Popular in

August

Cheapest in

February

Average price

C$ 506
Delta
  • Delta
  • 4/10-15/10
  • 2 total stops
  • 15h 16m total
  • Toronto to Chicago
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Delta
  • Delta
  • 1/9
  • 1 total stop
  • 7h 23m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 118 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 18 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 3 julio 2025.

sáb. 4/1012:14 p.m.YYZ - MDW
1 stop7h 21mDelta
mié. 15/102:00 p.m.MDW - YYZ
1 stop7h 55mDelta
Deal found 1/7C$ 292
vie. 15/87:21 p.m.YYZ - MDW
1 stop18h 42mWestJet
vie. 22/812:43 p.m.MDW - YYZ
1 stop8h 15mWestJet
Deal found 2/7C$ 349

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 629,999 searches. Data last updated 3 julio 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

sáb. 4/10

12:14 p.m.-6:35 p.m.

1 stop7h 21m

Chicago Midway

mié. 15/10

2:00 p.m.-10:55 p.m.

1 stop7h 55m

C$ 292

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

vie. 15/8

7:21 p.m.-1:03 p.m.

1 stop18h 42m

Chicago Midway

vie. 22/8

12:43 p.m.-9:58 p.m.

1 stop8h 15m

C$ 349

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

lun. 1/9

12:14 p.m.-6:37 p.m.

1 stop7h 23m

C$ 184

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

sáb. 30/8

1:20 p.m.-9:12 p.m.

1 stop8h 52m

C$ 211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

vie. 22/8

11:00 a.m.-6:05 p.m.

1 stop8h 05m

C$ 218

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/6

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, June is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of C$ 238). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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.

What is the cheapest time of day to fly from YYZ to MDW?

Find hourly flight availability from Pearson Intl to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 3 julio 2025.

It’s optimal to fly from Toronto Pearson Intl Airport to Chicago Midway Airport in the evening. By choosing this option you can save up to 35% on the cost of your flight, compared to a flight in the afternoon.

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 3 julio 2025.
Read reviews from past customers who have flown Delta and WestJet from Toronto Pearson Intl Airport to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,982 reviews
Check prices

Overall

8.0

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews
Check prices

Overall

8.0

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,917 reviews
Delta
8.0
Very good
7,982 reviews
Check prices

Overall

8.0

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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?

    Our cheapest airline available from Toronto Pearson Intl Airport to Chicago Midway Airport is Delta. Our recent data shows that you can find tickets from as low as C$ 292 on this airline. An additional option worth looking into is WestJet, starting at C$ 349. These flights start at 31% lower than the current average price 3 months from now.

  • 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, June is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of C$ 238). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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

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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.
Pearson Intl to O'Hare Intl flights
Toronto Island to Midway flights
Toronto Island to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights
Hamilton to O'Hare Intl flights

Top 2 airlines flying from Pearson Intl to Midway

Discover the top 2 airlines that operate flights from Pearson Intl to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 3 julio 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 238AverageC$ 355FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 470AverageC$ 668FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Pearson Intl to Midway?

Cheapflights makes it easy to find Pearson Intl to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Pearson Intl to Midway?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Pearson Intl to Midway.

Can Cheapflights find flights from Pearson Intl to Midway with no change fees?

Yes, we can. To see specific flights from Pearson Intl to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Pearson Intl to Midway become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Midway from Pearson Intl today and book when prices fit your budget.

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