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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 200

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 29/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
16 Oct — 23 Oct1
1 adult
1 adult, Economy

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 16 September 2025.

Round-trip from

C$ 326

One-way from

C$ 200

Popular in

September

Cheapest in

February

Average price

C$ 781
WestJet
  • WestJet
  • 18/10-25/10
  • 2 total stops
  • 10h 25m total
  • Toronto to Chicago
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29/10
  • 29/10
  • 1 total stop
  • 16h 57m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 26% potential increase in price (C$ 218 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease (C$ 45 potential savings vs. average RT price).
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Average for round-trip flights in September 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 16 September 2025.

Sat 18/106:20 a.m.YYZ - MDW
1 stop5h 10mWestJet
Sat 25/1010:35 a.m.MDW - YYZ
1 stop5h 15mWestJet
Deal found 14/9C$ 326
Thu 16/106:00 p.m.YYZ - MDW
1 stop5h 14mMultiple Airlines
Fri 31/109:32 a.m.MDW - YYZ
1 stop9h 28mMultiple Airlines
Deal found 14/9C$ 350
Thu 30/105:15 p.m.YYZ - MDW
1 stop16h 17mMultiple Airlines
Mon 3/119:32 a.m.MDW - YYZ
1 stop27h 33mMultiple Airlines
Deal found 15/9C$ 351
Tue 21/106:00 p.m.YYZ - MDW
1 stop5h 14mMultiple Airlines
Fri 31/109:32 a.m.MDW - YYZ
1 stop9h 28mMultiple Airlines
Deal found 14/9C$ 354
Mon 13/107:45 a.m.YYZ - MDW
1 stop15h 29mWestJet
Tue 21/101:48 p.m.MDW - YYZ
1 stop8h 30mWestJet
Deal found 14/9C$ 356
Wed 29/106:00 p.m.YYZ - MDW
1 stop16h 45mWestJet
Wed 5/1110:40 a.m.MDW - YYZ
1 stop10h 15mWestJet
Deal found 14/9C$ 359
Wed 15/106:00 p.m.YYZ - MDW
1 stop5h 14mWestJet
Tue 21/1012:48 p.m.MDW - YYZ
1 stop8h 07mWestJet
Deal found 15/9C$ 362
Thu 16/1011:52 a.m.YYZ - MDW
1 stop11h 22mWestJet
Sat 18/1010:35 a.m.MDW - YYZ
1 stop5h 15mWestJet
Deal found 15/9C$ 366
Mon 20/106:00 p.m.YYZ - MDW
1 stop5h 14mWestJet
Wed 22/109:20 a.m.MDW - YYZ
2 stops12h 32mWestJet
Deal found 15/9C$ 367

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 16 September 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 1/11

6:30 p.m.-10:45 a.m.

2 stops17h 15m

Chicago Midway

Mon 3/11

10:30 a.m.-4:50 p.m.

1 stop5h 20m

C$ 365

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 31/10

12:50 p.m.-10:26 a.m.

1 stop22h 36m

Chicago Midway

Fri 7/11

7:50 a.m.-5:12 p.m.

1 stop8h 22m

C$ 367

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 17/10

6:00 p.m.-10:14 p.m.

1 stop5h 14m

Chicago Midway

Tue 21/10

12:48 p.m.-9:55 p.m.

1 stop8h 07m

C$ 374

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 11/10

1:20 p.m.-10:14 p.m.

1 stop9h 54m

Chicago Midway

Tue 14/10

9:20 a.m.-6:13 a.m.

2 stops19h 53m

C$ 376

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 1/11

6:20 a.m.-1:08 p.m.

1 stop7h 48m

Chicago Midway

Tue 4/11

10:40 a.m.-4:50 p.m.

1 stop5h 10m

C$ 380

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 13/10

7:45 a.m.-10:14 p.m.

1 stop15h 29m

Chicago Midway

Sat 18/10

10:35 a.m.-9:55 p.m.

1 stop10h 20m

C$ 380

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 16/10

7:45 a.m.-10:14 p.m.

1 stop15h 29m

Chicago Midway

Sat 18/10

10:35 a.m.-9:55 p.m.

1 stop10h 20m

C$ 380

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 7/11

6:00 p.m.-9:40 a.m.

1 stop16h 40m

Chicago Midway

Sun 9/11

10:47 a.m.-5:00 p.m.

1 stop5h 13m

C$ 380

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 18/10

6:20 a.m.-10:30 a.m.

1 stop5h 10m

Chicago Midway

Tue 21/10

1:48 p.m.-11:18 p.m.

1 stop8h 30m

C$ 380

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 12/10

6:00 p.m.-10:14 p.m.

1 stop5h 14m

Chicago Midway

Sat 18/10

10:35 a.m.-9:55 p.m.

1 stop10h 20m

C$ 380

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/9

Showing 1-10 of 20 results
1
2

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, September is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of C$ 207). 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 16 September 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 36% 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 16 September 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
7.9
Good
363 reviews
Check prices

Overall

7.9

Food

7.6

Crew

8.6

Comfort

7.9

Entertainment

7.0

Boarding

8.1

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
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Overall

7.9

Food

7.6

Crew

8.6

Comfort

7.9

Entertainment

7.0

Boarding

8.1

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
3,091 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Overall

7.9

Food

7.6

Crew

8.6

Comfort

7.9

Entertainment

7.0

Boarding

8.1

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 WestJet fly from Toronto Pearson Intl Airport to Chicago Midway Airport in about 17h 15m. 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$ 228 on this airline. An additional option worth looking into is WestJet, starting at C$ 421. These flights start at 47% 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, September is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of C$ 207). 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 16 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 228AverageC$ 349FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 421AverageC$ 677FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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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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