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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 185

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 15/2. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
11 Jan — 18 Jan1
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 12 December 2025.

Wed 31/127:15 a.m.YYZ - MDW
2 stops15h 43mMultiple Airlines
Sat 3/16:08 p.m.MDW - YYZ
1 stop13h 50mMultiple Airlines
Deal found 9/12C$ 531
Wed 31/127:15 a.m.YYZ - MDW
1 stop15h 43mMultiple Airlines
Sun 4/17:44 a.m.MDW - YYZ
2 stops31h 41mMultiple Airlines
Deal found 10/12C$ 583
Tue 30/128:20 p.m.YYZ - MDW
2 stops26h 52mMultiple Airlines
Sun 4/16:08 p.m.MDW - YYZ
1 stop13h 56mMultiple Airlines
Deal found 10/12C$ 607
Wed 31/126:05 a.m.YYZ - MDW
1 stop3h 44mWestJet
Fri 2/19:29 a.m.MDW - YYZ
1 stop22h 29mWestJet
Deal found 8/12C$ 655
Wed 24/1210:15 p.m.YYZ - MDW
2 stops20h 04mWestJet
Fri 26/129:29 a.m.MDW - YYZ
1 stop12h 21mWestJet
Deal found 9/12C$ 656
Wed 24/1210:15 p.m.YYZ - MDW
2 stops20h 04mWestJet
Wed 31/129:50 a.m.MDW - YYZ
1 stop24h 18mWestJet
Deal found 10/12C$ 677

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 12 December 2025.

Round-trip from

C$ 292

One-way from

C$ 185

Popular in

September

Cheapest in

December

Average price

C$ 295
Delta
  • Delta
  • 5/2-8/2
  • 2 total stops
  • 12h 10m total
  • Toronto to Chicago
Search Deals
Delta
  • Delta
  • 15/2
  • 1 total stop
  • 5h 33m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 31% potential increase in price (C$ 269 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 45 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 12 December 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

Thu 5/2

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

1 stop6h 01m

Chicago Midway

Sun 8/2

1:26 p.m.-7:08 p.m.

1 stop4h 42m

C$ 292

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 29/1

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

1 stop6h 01m

Chicago Midway

Sun 1/2

1:26 p.m.-7:08 p.m.

1 stop4h 42m

C$ 310

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 15/1

7:45 a.m.-12:48 p.m.

1 stop6h 03m

Chicago Midway

Mon 19/1

1:26 p.m.-7:08 p.m.

1 stop4h 42m

C$ 325

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 26/1

6:00 a.m.-12:46 p.m.

1 stop7h 46m

Chicago Midway

Thu 29/1

1:26 p.m.-10:42 p.m.

1 stop8h 16m

C$ 327

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 18/1

6:30 a.m.-1:09 p.m.

1 stop7h 39m

Chicago Midway

Thu 22/1

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

1 stop5h 09m

C$ 327

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 16/1

6:30 a.m.-1:09 p.m.

1 stop7h 39m

Chicago Midway

Mon 19/1

6:35 p.m.-10:42 p.m.

1 stop3h 07m

C$ 327

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 25/1

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

1 stop6h 01m

Chicago Midway

Sun 1/2

1:26 p.m.-10:42 p.m.

1 stop8h 16m

C$ 327

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 24/2

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

1 stop3h 41m

C$ 185

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 15/2

6:30 a.m.-11:03 a.m.

1 stop5h 33m

C$ 185

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 31/1

6:00 a.m.-8:52 a.m.

1 stop3h 52m

C$ 201

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 18 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$ 178). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in October is currently the most expensive (average of C$ 476). 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 12 December 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 12 December 2025.
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
8.0
Very good
397 reviews
Check prices

Entertainment

7.0

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.6

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
8.0
Very good
397 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Entertainment

7.0

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.6

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 6h 01m. 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$ 228 on this airline. This flight 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, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of C$ 178). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in October is currently the most expensive (average of C$ 476). 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 12 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 228AverageC$ 346FlexibilityNo 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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