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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 201

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 26/3. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
11 Mar — 18 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap 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 9 February 2026.

Thu 26/26:30 a.m.
YYZ
-
MDW
1 stop7h 35m
Delta
Sun 1/39:34 a.m.
MDW
-
YYZ
1 stop5h 36m
Delta
Deal found 5/2C$ 309
Fri 27/26:10 a.m.
YYZ
-
MDW
1 stop3h 44m
Delta
Sun 1/39:34 a.m.
MDW
-
YYZ
1 stop5h 36m
Delta
Deal found 6/2C$ 320
Fri 6/312:11 p.m.
YYZ
-
MDW
1 stop6h 26m
WestJet
Fri 13/39:35 a.m.
MDW
-
YYZ
1 stop6h 42m
WestJet
Deal found 6/2C$ 384
Thu 5/37:10 a.m.
YYZ
-
MDW
1 stop8h 16m
Multiple Airlines
Mon 9/39:51 p.m.
MDW
-
YYZ
2 stops21h 19m
Multiple Airlines
Deal found 7/2C$ 390
Sun 8/310:05 a.m.
YYZ
-
MDW
1 stop3h 24m
Delta
Tue 10/39:35 a.m.
MDW
-
YYZ
1 stop4h 33m
Delta
Deal found 6/2C$ 394
Thu 2/46:30 a.m.
YYZ
-
MDW
1 stop7h 55m
WestJet
Sun 5/49:30 a.m.
MDW
-
YYZ
1 stop12h 36m
WestJet
Deal found 8/2C$ 399
Wed 11/312:15 p.m.
YYZ
-
MDW
1 stop6h 39m
WestJet
Wed 18/39:35 a.m.
MDW
-
YYZ
1 stop4h 33m
WestJet
Deal found 6/2C$ 402
Mon 9/312:15 p.m.
YYZ
-
MDW
1 stop6h 39m
WestJet
Wed 1/79:30 a.m.
MDW
-
YYZ
1 stop4h 48m
WestJet
Deal found 9/2C$ 403
Fri 10/46:20 a.m.
YYZ
-
MDW
1 stop3h 33m
WestJet
Sun 12/46:34 p.m.
MDW
-
YYZ
1 stop3h 05m
WestJet
Deal found 7/2C$ 405
Fri 27/210:05 a.m.
YYZ
-
MDW
1 stop3h 41m
WestJet
Sun 1/39:34 a.m.
MDW
-
YYZ
1 stop5h 36m
WestJet
Deal found 6/2C$ 406

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 9 February 2026.

Round-trip from

C$ 309

One-way from

C$ 201

Popular in

September

Cheapest in

December

Average price

C$ 385
Delta
  • Delta
  • 26/2-1/3
  • 2 total stops
  • 13h 11m total
  • Toronto to Chicago
Search Deals
Delta
  • Delta
  • 26/3
  • 1 total stop
  • 3h 33m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 29% potential increase in price (C$ 250 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 47 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 629,999 searches. Data last updated 9 February 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

Thu 26/2

6:30 a.m.-1:05 p.m.

1 stop7h 35m

Chicago Midway

Sun 1/3

9:34 a.m.-4:10 p.m.

1 stop5h 36m

C$ 309

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 6/3

6:10 a.m.-8:54 a.m.

1 stop3h 44m

Chicago Midway

Fri 13/3

6:34 p.m.-10:39 p.m.

1 stop3h 05m

C$ 320

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 24/5

12:29 p.m.-5:56 p.m.

1 stop6h 27m

Chicago Midway

Tue 26/5

6:36 p.m.-10:59 p.m.

1 stop3h 23m

C$ 320

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 26/3

6:20 a.m.-8:53 a.m.

1 stop3h 33m

Chicago Midway

Thu 2/4

9:30 a.m.-3:59 p.m.

1 stop5h 29m

C$ 320

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 23/4

2:15 p.m.-5:58 p.m.

1 stop4h 43m

Chicago Midway

Mon 4/5

9:31 a.m.-6:31 p.m.

1 stop8h 00m

C$ 320

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 27/2

6:10 a.m.-8:54 a.m.

1 stop3h 44m

Chicago Midway

Sun 1/3

9:34 a.m.-4:10 p.m.

1 stop5h 36m

C$ 320

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 27/4

2:15 p.m.-5:58 p.m.

1 stop4h 43m

Chicago Midway

Fri 1/5

9:27 a.m.-5:21 p.m.

1 stop6h 54m

C$ 320

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 5/3

7:45 a.m.-12:46 p.m.

1 stop6h 01m

Chicago Midway

Mon 9/3

1:10 p.m.-5:17 p.m.

1 stop3h 07m

C$ 320

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 20/5

6:10 a.m.-8:43 a.m.

1 stop3h 33m

Chicago Midway

Thu 21/5

9:22 a.m.-5:21 p.m.

1 stop6h 59m

C$ 320

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 25/3

6:20 a.m.-8:53 a.m.

1 stop3h 33m

Chicago Midway

Fri 27/3

2:05 p.m.-11:06 p.m.

1 stop8h 01m

C$ 320

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/2

Showing 1-10 of 18 results
1
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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

How often are flights from Toronto to Chicago delayed?

About 26% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 51 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 past year, Air Canada has had the lowest number of delays on this route, with just 67% of flights being delayed.

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 9 February 2026.
Read reviews from past customers who have flown Porter Airlines 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
414 reviews
Check prices

Comfort

7.9

Crew

8.6

Food

7.5

Entertainment

6.9

Boarding

8.2

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.
Porter Airlines
7.9
Good
414 reviews
Porter Airlines
7.9
Good
414 reviews
Check prices

Comfort

7.9

Crew

8.6

Food

7.5

Entertainment

6.9

Boarding

8.2

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.

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 is the cheapest airline to fly 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$ 112 on this airline. This flight start at 74% 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.

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 airline flying from Pearson Intl to Midway

Discover the top airline 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 9 February 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 112AverageC$ 386FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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