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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 179

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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
18 Nov — 25 Nov1
1 adult
1 adult, Economy

Find flight deals from Pearson Intl to Midway

Enter your travel dates to find the best prices.

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 19 October 2025.

Tue 18/113:38 p.m.YYZ - MDW
1 stop3h 30mDelta
Sat 29/119:41 a.m.MDW - YYZ
1 stop5h 21mDelta
Deal found 17/10C$ 282
Thu 4/126:05 a.m.YYZ - MDW
1 stop3h 49mKLM
Mon 8/126:40 p.m.MDW - YYZ
1 stop3h 31mKLM
Deal found 19/10C$ 289
Sat 8/116:20 a.m.YYZ - MDW
1 stop5h 10mDelta
Mon 10/116:48 p.m.MDW - YYZ
1 stop3h 17mDelta
Deal found 16/10C$ 294
Mon 24/116:30 a.m.YYZ - MDW
1 stop7h 37mDelta
Sun 30/119:34 a.m.MDW - YYZ
1 stop6h 41mDelta
Deal found 18/10C$ 296
Wed 12/116:05 a.m.YYZ - MDW
1 stop3h 49mKLM
Fri 14/116:48 p.m.MDW - YYZ
1 stop3h 17mKLM
Deal found 17/10C$ 303
Fri 21/116:05 a.m.YYZ - MDW
1 stop7h 29mDelta
Sun 23/116:48 p.m.MDW - YYZ
1 stop3h 17mDelta
Deal found 19/10C$ 322
Sun 16/116:30 a.m.YYZ - MDW
1 stop7h 37mDelta
Sun 23/116:48 p.m.MDW - YYZ
1 stop3h 17mDelta
Deal found 17/10C$ 349
Sat 22/116:30 a.m.YYZ - MDW
1 stop7h 37mWestJet
Tue 25/119:41 a.m.MDW - YYZ
1 stop5h 21mWestJet
Deal found 18/10C$ 369
Fri 26/126:00 a.m.YYZ - MDW
1 stop6h 06mWestJet
Mon 29/1211:48 a.m.MDW - YYZ
1 stop10h 32mWestJet
Deal found 17/10C$ 370
Tue 11/117:15 a.m.YYZ - MDW
2 stops17h 40mMultiple Airlines
Mon 17/119:27 a.m.MDW - YYZ
1 stop9h 33mMultiple Airlines
Deal found 18/10C$ 377
Tue 16/126:12 p.m.YYZ - MDW
1 stop16h 42mWestJet
Wed 17/121:50 p.m.MDW - YYZ
1 stop8h 37mWestJet
Deal found 17/10C$ 381

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 19 October 2025.

Round-trip from

C$ 282

One-way from

C$ 179

Popular in

September

Cheapest in

February

Average price

C$ 648
Delta
  • Delta
  • 18/11-28/11
  • 2 total stops
  • 10h 30m total
  • Toronto to Chicago
Search Deals
Delta
  • Delta
  • 11/11
  • 1 total stop
  • 7h 37m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 31% potential increase in price (C$ 296 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 44 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 629,999 searches. Data last updated 19 October 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

Tue 20/1

6:00 a.m.-12:35 p.m.

1 stop7h 35m

Chicago Midway

Thu 12/2

1:00 p.m.-7:09 p.m.

1 stop5h 09m

C$ 282

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 27/11

6:05 a.m.-8:54 a.m.

1 stop3h 49m

Chicago Midway

Fri 28/11

9:41 a.m.-4:02 p.m.

1 stop5h 21m

C$ 282

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 22/11

10:05 a.m.-12:46 p.m.

1 stop3h 41m

Chicago Midway

Mon 1/12

6:48 p.m.-11:05 p.m.

1 stop3h 17m

C$ 282

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 21/1

10:10 a.m.-12:35 p.m.

1 stop3h 25m

Chicago Midway

Thu 12/2

1:00 p.m.-7:09 p.m.

1 stop5h 09m

C$ 282

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 20/11

6:30 a.m.-1:07 p.m.

1 stop7h 37m

Chicago Midway

Sat 29/11

6:48 p.m.-11:05 p.m.

1 stop3h 17m

C$ 282

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 21/11

6:05 a.m.-12:34 p.m.

1 stop7h 29m

Chicago Midway

Mon 1/12

6:48 p.m.-11:05 p.m.

1 stop3h 17m

C$ 282

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 20/11

3:38 p.m.-6:08 p.m.

1 stop3h 30m

Chicago Midway

Mon 1/12

6:48 p.m.-11:05 p.m.

1 stop3h 17m

C$ 282

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 20/11

12:08 p.m.-6:08 p.m.

1 stop7h 00m

Chicago Midway

Tue 2/12

1:14 p.m.-5:15 p.m.

1 stop3h 01m

C$ 282

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 25/11

9:52 a.m.-12:34 p.m.

1 stop3h 42m

Chicago Midway

Fri 28/11

9:41 a.m.-4:02 p.m.

1 stop5h 21m

C$ 282

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 4/12

6:05 a.m.-8:54 a.m.

1 stop3h 49m

Chicago Midway

Mon 8/12

6:40 p.m.-11:11 p.m.

1 stop3h 31m

C$ 289

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/10

Showing 1-10 of 24 results
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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 C$ 181). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in October is currently the most expensive (average of C$ 489). 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 19 October 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 34% 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 19 October 2025.
Read reviews from past customers who have flown Porter Airlines 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.
Porter Airlines
8.0
Very good
381 reviews
Check prices

Comfort

8.0

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
8.0
Very good
381 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Comfort

8.0

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
WestJet
7.2
Good
3,129 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Comfort

8.0

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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?

    Airlines like Delta fly from Toronto Pearson Intl Airport to Chicago Midway Airport in about 7h 35m. The time it takes to get you to your destination can typically vary by up to . The distance from Toronto Pearson Intl Airport to Chicago Midway Airport is about 695 km.

  • 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 Porter Airlines. Our recent data shows that you can find tickets from as low as C$ 231 on this airline. An additional option worth looking into is WestJet, starting at C$ 557. These flights start at 48% 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, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of C$ 181). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in October is currently the most expensive (average of C$ 489). 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
Hamilton to O'Hare Intl flights
Region of Waterloo Intl 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 19 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 231AverageC$ 354FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 557AverageC$ 687FlexibilityNo 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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