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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 187

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 25/7. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
9 Apr — 16 Apr1
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 10 March 2026.

Thu 21/512:09 p.m.
YYZ
-
MDW
1 stop7h 24m
Delta
Sun 24/59:22 a.m.
MDW
-
YYZ
1 stop6h 59m
Delta
Deal found 5/3C$ 305
Thu 16/412:16 p.m.
YYZ
-
MDW
1 stop6h 42m
Delta
Mon 20/49:29 a.m.
MDW
-
YYZ
1 stop8h 02m
Delta
Deal found 5/3C$ 327
Thu 18/66:00 a.m.
YYZ
-
MDW
1 stop7h 30m
Delta
Sun 21/69:30 a.m.
MDW
-
YYZ
1 stop6h 53m
Delta
Deal found 5/3C$ 338
Fri 17/46:10 a.m.
YYZ
-
MDW
1 stop3h 37m
Delta
Sun 19/46:38 p.m.
MDW
-
YYZ
1 stop3h 18m
Delta
Deal found 6/3C$ 349
Fri 3/412:15 p.m.
YYZ
-
MDW
1 stop6h 39m
Delta
Fri 10/46:34 p.m.
MDW
-
YYZ
1 stop3h 05m
Delta
Deal found 5/3C$ 358
Thu 9/712:15 p.m.
YYZ
-
MDW
1 stop7h 16m
Delta
Mon 13/72:00 p.m.
MDW
-
YYZ
1 stop7h 58m
Delta
Deal found 5/3C$ 370
Fri 24/42:15 p.m.
YYZ
-
MDW
1 stop4h 43m
Delta
Fri 1/59:27 a.m.
MDW
-
YYZ
1 stop4h 53m
Delta
Deal found 10/3C$ 372
Wed 1/46:20 a.m.
YYZ
-
MDW
1 stop3h 33m
Delta
Sun 5/49:35 a.m.
MDW
-
YYZ
1 stop4h 33m
Delta
Deal found 9/3C$ 373
Tue 2/62:20 p.m.
YYZ
-
MDW
1 stop5h 13m
Delta
Sun 7/69:30 a.m.
MDW
-
YYZ
1 stop6h 53m
Delta
Deal found 6/3C$ 380
Sat 25/42:15 p.m.
YYZ
-
MDW
1 stop4h 43m
Delta
Sat 2/51:24 p.m.
MDW
-
YYZ
1 stop8h 32m
Delta
Deal found 6/3C$ 381

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 10 March 2026.

Round-trip from

C$ 305

One-way from

C$ 187

Popular in

September

Cheapest in

December

Average price

C$ 358
Delta
  • Delta
  • 21/5-24/5
  • 2 total stops
  • 14h 23m total
  • Toronto to Chicago
Search Deals
Delta
  • Delta
  • 24/7
  • 1 total stop
  • 7h 16m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 23% potential increase in price (C$ 182 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 10 March 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 17/4

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

1 stop6h 42m

Chicago Midway

Mon 20/4

2:12 p.m.-11:10 p.m.

1 stop7h 58m

C$ 327

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 16/4

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

1 stop6h 42m

Chicago Midway

Mon 20/4

9:29 a.m.-6:31 p.m.

1 stop8h 02m

C$ 327

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 14/4

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

1 stop4h 43m

Chicago Midway

Sat 18/4

1:24 p.m.-10:56 p.m.

1 stop8h 32m

C$ 327

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 5/6

2:20 p.m.-6:33 p.m.

1 stop5h 13m

Chicago Midway

Sun 7/6

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

1 stop6h 53m

C$ 349

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 22/4

6:10 a.m.-8:47 a.m.

1 stop3h 37m

Chicago Midway

Sat 25/4

1:24 p.m.-10:56 p.m.

1 stop8h 32m

C$ 350

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 8/4

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

1 stop3h 33m

Chicago Midway

Tue 21/4

1:24 p.m.-10:56 p.m.

1 stop8h 32m

C$ 350
Quickest round-trip

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/4

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

1 stop7h 09m

Chicago Midway

Sat 11/4

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

1 stop3h 05m

C$ 350

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 1/4

12:15 p.m.-5:54 p.m.

1 stop6h 39m

Chicago Midway

Tue 7/4

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

1 stop8h 01m

C$ 351
Cheapest one-way

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 25/7

2:15 p.m.-6:31 p.m.

1 stop5h 16m

C$ 187

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 24/7

12:15 p.m.-6:31 p.m.

1 stop7h 16m

C$ 187

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/3

Showing 1-10 of 19 resultsSorted by cheapest first
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

How often are flights from Toronto to Chicago delayed?

About 23% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 53 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, Delta has had the lowest number of delays on this route, with just 42% 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 10 March 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
8.0
Very good
423 reviews
Check prices

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
423 reviews
Porter Airlines
8.0
Very good
423 reviews
Check prices

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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 42m. 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$ 111 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 10 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 111AverageC$ 383FlexibilityNo 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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