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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 188

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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
26 Feb — 5 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 27 January 2026.

Wed 6/52:15 p.m.
YYZ
-
MDW
1 stop4h 43m
Delta
Sat 16/59:30 a.m.
MDW
-
YYZ
1 stop6h 53m
Delta
Deal found 27/1C$ 308
Thu 19/27:45 a.m.
YYZ
-
MDW
1 stop6h 01m
Delta
Mon 23/26:17 p.m.
MDW
-
YYZ
1 stop3h 23m
Delta
Deal found 26/1C$ 311
Fri 20/36:20 a.m.
YYZ
-
MDW
1 stop3h 33m
WestJet
Fri 27/32:05 p.m.
MDW
-
YYZ
1 stop8h 01m
WestJet
Deal found 27/1C$ 323
Mon 2/312:11 p.m.
YYZ
-
MDW
1 stop6h 26m
WestJet
Fri 6/31:49 p.m.
MDW
-
YYZ
1 stop8h 22m
WestJet
Deal found 26/1C$ 325
Tue 10/212:12 p.m.
YYZ
-
MDW
1 stop6h 43m
Delta
Wed 18/26:20 p.m.
MDW
-
YYZ
1 stop3h 20m
Delta
Deal found 27/1C$ 327
Tue 10/26:30 a.m.
YYZ
-
MDW
1 stop7h 36m
Delta
Tue 17/21:28 p.m.
MDW
-
YYZ
1 stop8h 12m
Delta
Deal found 26/1C$ 340
Tue 10/210:05 a.m.
YYZ
-
MDW
1 stop3h 41m
Delta
Fri 13/21:49 p.m.
MDW
-
YYZ
1 stop8h 22m
Delta
Deal found 27/1C$ 361
Wed 11/210:05 a.m.
YYZ
-
MDW
1 stop3h 41m
Delta
Sun 15/29:34 a.m.
MDW
-
YYZ
1 stop5h 36m
Delta
Deal found 26/1C$ 371
Mon 9/26:00 a.m.
YYZ
-
MDW
1 stop7h 46m
Delta
Wed 11/29:53 a.m.
MDW
-
YYZ
1 stop5h 06m
Delta
Deal found 26/1C$ 374
Mon 16/36:20 a.m.
YYZ
-
MDW
1 stop7h 09m
Delta
Tue 17/36:34 p.m.
MDW
-
YYZ
1 stop3h 05m
Delta
Deal found 25/1C$ 385
Fri 13/26:15 a.m.
YYZ
-
MDW
1 stop7h 31m
Delta
Mon 16/21:26 p.m.
MDW
-
YYZ
1 stop8h 14m
Delta
Deal found 25/1C$ 394

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 27 January 2026.

Round-trip from

C$ 308

One-way from

C$ 188

Popular in

September

Cheapest in

December

Average price

C$ 519
Delta
  • Delta
  • 19/2-21/2
  • 2 total stops
  • 11h 12m total
  • Toronto to Chicago
Search Deals
Delta
  • Delta
  • 29/3
  • 1 total stop
  • 3h 33m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 30% potential increase in price (C$ 260 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 27 January 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 19/2

6:15 a.m.-8:54 a.m.

1 stop3h 39m

Chicago Midway

Mon 23/2

1:49 p.m.-11:11 p.m.

1 stop8h 22m

C$ 308

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 7/3

6:15 a.m.-8:54 a.m.

1 stop3h 39m

Chicago Midway

Wed 11/3

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

1 stop5h 29m

C$ 308

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 12/3

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

1 stop3h 33m

Chicago Midway

Mon 16/3

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

1 stop3h 07m

C$ 308

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 7/3

6:15 a.m.-12:46 p.m.

1 stop7h 31m

Chicago Midway

Fri 13/3

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

1 stop3h 05m

C$ 308

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 21/4

12:16 p.m.-5:58 p.m.

1 stop6h 42m

Chicago Midway

Fri 24/4

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

1 stop8h 00m

C$ 308

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 17/2

12:11 p.m.-5:37 p.m.

1 stop6h 26m

Chicago Midway

Tue 24/2

9:50 a.m.-3:59 p.m.

1 stop5h 09m

C$ 308

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 9/3

6:20 a.m.-12:29 p.m.

1 stop7h 09m

Chicago Midway

Thu 12/3

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

1 stop3h 07m

C$ 308

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 11/3

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

1 stop3h 33m

Chicago Midway

Thu 12/3

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

1 stop5h 29m

C$ 308

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 3/5

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

1 stop4h 43m

Chicago Midway

Sun 10/5

9:20 a.m.-6:25 p.m.

1 stop8h 05m

C$ 308

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 3/5

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

1 stop4h 43m

Chicago Midway

Thu 14/5

9:20 a.m.-6:25 p.m.

1 stop8h 05m

C$ 308

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/1

Showing 1-10 of 21 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$ 177). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in October is currently the most expensive (average of C$ 472). 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.

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 27 January 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
412 reviews
Check prices

Entertainment

6.9

Crew

8.6

Food

7.5

Overall

7.9

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
7.9
Good
412 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Entertainment

6.9

Crew

8.6

Food

7.5

Overall

7.9

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands 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.

  • 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 3h 39m. 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.

  • 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$ 177). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in October is currently the most expensive (average of C$ 472). 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 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 27 January 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 112AverageC$ 343FlexibilityNo cancel feeOn-time52%
Search Porter Airlines 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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