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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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
23 Aug — 30 Aug1
1 adult

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 18 August 2025.

Round-trip from

C$ 280

One-way from

C$ 185

Popular in

August

Cheapest in

February

Average price

C$ 548
Delta
  • Delta
  • 4/11-11/11
  • 2 total stops
  • 15h 15m total
  • Toronto to Chicago
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Delta
  • Delta
  • 1/10
  • 1 total stop
  • 6h 58m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 18 August 2025.

Tue 4/116:15 a.m.YYZ - MDW
1 stop7h 13mDelta
Wed 12/119:30 a.m.MDW - YYZ
1 stop6h 53mDelta
Deal found 16/8C$ 280
Tue 7/1012:15 p.m.YYZ - MDW
1 stop7h 10mDelta
Sat 11/103:00 p.m.MDW - YYZ
1 stop7h 18mDelta
Deal found 18/8C$ 293
Wed 1/101:20 p.m.YYZ - MDW
1 stop9h 16mWestJet
Wed 8/109:20 a.m.MDW - YYZ
1 stop12h 58mWestJet
Deal found 17/8C$ 305
Wed 8/1012:15 p.m.YYZ - MDW
1 stop7h 10mDelta
Sun 12/109:35 a.m.MDW - YYZ
1 stop4h 10mDelta
Deal found 18/8C$ 309
Fri 26/912:15 p.m.YYZ - MDW
1 stop7h 20mDelta
Tue 30/99:35 a.m.MDW - YYZ
1 stop6h 48mDelta
Deal found 18/8C$ 326
Mon 6/1012:15 p.m.YYZ - MDW
1 stop7h 10mDelta
Sat 11/106:23 p.m.MDW - YYZ
1 stop3h 32mDelta
Deal found 18/8C$ 341
Sat 18/106:00 p.m.YYZ - MDW
1 stop5h 14mWestJet
Sat 25/103:00 p.m.MDW - YYZ
1 stop7h 18mWestJet
Deal found 15/8C$ 356
Thu 25/912:15 p.m.YYZ - MDW
1 stop7h 20mDelta
Mon 29/99:35 a.m.MDW - YYZ
1 stop6h 48mDelta
Deal found 18/8C$ 358
Wed 10/91:20 p.m.YYZ - MDW
1 stop9h 06mWestJet
Wed 17/912:43 p.m.MDW - YYZ
1 stop10h 12mWestJet
Deal found 17/8C$ 362
Wed 15/106:00 p.m.YYZ - MDW
1 stop5h 14mWestJet
Tue 21/1012:48 p.m.MDW - YYZ
1 stop8h 07mWestJet
Deal found 16/8C$ 363
Sun 21/98:00 p.m.YYZ - MDW
1 stop12h 23mMultiple Airlines
Fri 26/96:21 a.m.MDW - YYZ
1 stop14h 00mMultiple Airlines
Deal found 16/8C$ 364
Sat 13/96:15 a.m.YYZ - MDW
1 stop15h 55mMultiple Airlines
Fri 19/96:21 a.m.MDW - YYZ
1 stop14h 00mMultiple Airlines
Deal found 17/8C$ 366

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 18 August 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

Wed 5/11

12:15 p.m.-6:25 p.m.

1 stop7h 10m

Chicago Midway

Sat 8/11

1:06 p.m.-5:19 p.m.

1 stop3h 13m

C$ 280

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 5/11

12:15 p.m.-6:25 p.m.

1 stop7h 10m

Chicago Midway

Mon 10/11

9:30 a.m.-5:23 p.m.

1 stop6h 53m

C$ 280

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 8/11

12:15 p.m.-6:25 p.m.

1 stop7h 10m

Chicago Midway

Mon 10/11

9:30 a.m.-5:23 p.m.

1 stop6h 53m

C$ 280

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 23/10

12:15 p.m.-6:25 p.m.

1 stop7h 10m

Chicago Midway

Mon 27/10

9:35 a.m.-5:19 p.m.

1 stop6h 44m

C$ 280

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 25/10

12:15 p.m.-6:25 p.m.

1 stop7h 10m

Chicago Midway

Tue 28/10

9:35 a.m.-2:45 p.m.

1 stop4h 10m

C$ 280

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 24/10

12:15 p.m.-6:25 p.m.

1 stop7h 10m

Chicago Midway

Tue 28/10

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

1 stop8h 30m

C$ 280

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 10/11

6:00 a.m.-12:32 p.m.

1 stop7h 32m

Chicago Midway

Tue 11/11

2:00 p.m.-11:02 p.m.

1 stop8h 02m

C$ 280

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 10/11

12:15 p.m.-6:36 p.m.

1 stop7h 21m

Chicago Midway

Wed 12/11

9:30 a.m.-5:23 p.m.

1 stop6h 53m

C$ 280

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 21/10

6:15 a.m.-12:28 p.m.

1 stop7h 13m

Chicago Midway

Mon 27/10

9:35 a.m.-5:19 p.m.

1 stop6h 44m

C$ 280

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 24/10

12:15 p.m.-6:25 p.m.

1 stop7h 10m

Chicago Midway

Mon 27/10

9:35 a.m.-5:19 p.m.

1 stop6h 44m

C$ 280

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/8

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$ 232). 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 18 August 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.

What’s the top layover airport for flights from Toronto Pearson Intl Airport to Chicago Midway Airport?

Share of one-stop round-trip flights from Toronto Pearson Intl Airport to Chicago Midway Airport chosen by Cheapflights users in the past 12 months, using the same layover each way.

Atlanta (ATL) – chosen by Cheapflights users on 63% of one-stop itineraries from Toronto Pearson Intl Airport to Chicago Midway Airport on Cheapflights.

What’s the cheapest layover airport for flights from Toronto Pearson Intl Airport to Chicago Midway Airport?

Average round-trip fare for 1-stop flights from Toronto Pearson Intl Airport to Chicago Midway Airport, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of C$ 711.

What’s the fastest layover option from Toronto Pearson Intl Airport to Chicago Midway Airport?

Shortest average travel time for 1-stop one-way flights from Toronto Pearson Intl Airport to Chicago Midway Airport, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 5h 51m.

Which airport typically offers the quickest layover for flights from Toronto Pearson Intl Airport to Chicago Midway Airport?

Average layover duration for 1-stop one-way flights from Toronto Pearson Intl Airport to Chicago Midway Airport, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Atlanta (ATL) offer the fastest connection on this route, with an average layover time of 3h 28m.

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 18 August 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
334 reviews
Check prices

Entertainment

7.0

Food

7.6

Crew

8.7

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
334 reviews
Porter Airlines
8.0
Very good
334 reviews
Check prices

Entertainment

7.0

Food

7.6

Crew

8.7

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
3,018 reviews
Porter Airlines
8.0
Very good
334 reviews
Check prices

Entertainment

7.0

Food

7.6

Crew

8.7

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 10m. 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$ 548. These flights start at 45% 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$ 232). 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 18 August 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 228AverageC$ 359FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 548AverageC$ 676FlexibilityNo 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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