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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 207

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 14/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
22 Jul — 29 Jul1
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 22 June 2026.

Sat 5/912:09 p.m.
YYZ
-
MDW
1 stop5h 50m
Delta
Tue 8/95:45 p.m.
MDW
-
YYZ
1 stop4h 14m
Delta
Deal found 19/6C$ 335
Thu 24/92:24 p.m.
YYZ
-
MDW
1 stop5h 09m
Delta
Tue 29/99:30 a.m.
MDW
-
YYZ
1 stop4h 45m
Delta
Deal found 18/6C$ 338
Tue 21/712:09 p.m.
YYZ
-
MDW
1 stop7h 16m
Delta
Sat 25/79:19 a.m.
MDW
-
YYZ
1 stop7h 05m
Delta
Deal found 21/6C$ 342
Sat 1/86:10 a.m.
YYZ
-
MDW
1 stop7h 28m
KLM
Sat 8/81:27 p.m.
MDW
-
YYZ
1 stop8h 32m
KLM
Deal found 17/6C$ 345
Tue 7/76:10 a.m.
YYZ
-
MDW
1 stop4h 03m
Delta
Sat 11/76:35 p.m.
MDW
-
YYZ
1 stop3h 27m
Delta
Deal found 20/6C$ 352
Sat 18/76:10 a.m.
YYZ
-
MDW
1 stop4h 03m
Delta
Tue 21/79:19 a.m.
MDW
-
YYZ
1 stop3h 15m
Delta
Deal found 19/6C$ 354
Sat 11/712:09 p.m.
YYZ
-
MDW
1 stop6h 58m
Delta
Sat 18/79:19 a.m.
MDW
-
YYZ
1 stop5h 01m
Delta
Deal found 18/6C$ 355
Thu 3/96:10 a.m.
YYZ
-
MDW
1 stop7h 29m
Delta
Fri 4/91:27 p.m.
MDW
-
YYZ
1 stop8h 36m
Delta
Deal found 17/6C$ 381
Sat 25/76:10 a.m.
YYZ
-
MDW
1 stop7h 28m
Delta
Thu 27/89:24 a.m.
MDW
-
YYZ
1 stop7h 00m
Delta
Deal found 20/6C$ 385
Wed 15/76:10 a.m.
YYZ
-
MDW
1 stop4h 03m
Delta
Wed 22/79:19 a.m.
MDW
-
YYZ
1 stop3h 15m
Delta
Deal found 21/6C$ 386
Sat 18/76:10 a.m.
YYZ
-
MDW
1 stop4h 03m
Delta
Sat 25/79:19 a.m.
MDW
-
YYZ
1 stop7h 05m
Delta
Deal found 18/6C$ 388

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 22 June 2026.

Round-trip from

C$ 335

One-way from

C$ 207

Popular in

April

Cheapest in

December

Average price

C$ 512
Delta
  • Delta
  • 5/9-8/9
  • 2 total stops
  • 10h 04m total
  • Toronto to Chicago
Search Deals
KLM
  • KLM
  • 14/9
  • 1 total stop
  • 7h 25m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 144 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 44 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 22 June 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

Thu 6/8

6:10 a.m.-9:17 a.m.

1 stop4h 07m

Chicago Midway

Fri 7/8

1:25 p.m.-11:03 p.m.

1 stop8h 38m

C$ 352

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 7/8

6:10 a.m.-9:17 a.m.

1 stop4h 07m

Chicago Midway

Mon 10/8

1:27 p.m.-11:03 p.m.

1 stop8h 36m

C$ 354

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 28/7

6:10 a.m.-9:13 a.m.

1 stop4h 03m

Chicago Midway

Tue 4/8

6:42 p.m.-11:03 p.m.

1 stop3h 21m

C$ 354

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 11/7

12:09 p.m.-6:07 p.m.

1 stop6h 58m

Chicago Midway

Sat 18/7

9:19 a.m.-3:20 p.m.

1 stop5h 01m

C$ 355

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 8/10

12:15 p.m.-6:37 p.m.

1 stop7h 22m

Chicago Midway

Sun 11/10

9:30 a.m.-5:22 p.m.

1 stop6h 52m

C$ 381

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 18/7

6:10 a.m.-9:13 a.m.

1 stop4h 03m

Chicago Midway

Sat 25/7

9:19 a.m.-5:24 p.m.

1 stop7h 05m

C$ 388

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 4/8

6:10 a.m.-12:39 p.m.

1 stop7h 29m

Chicago Midway

Fri 7/8

1:25 p.m.-11:03 p.m.

1 stop8h 38m

C$ 418
Quickest round-trip

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 2/10

4:05 p.m.-6:33 p.m.

1 stop3h 28m

Chicago Midway

Mon 5/10

9:30 a.m.-1:34 p.m.

1 stop3h 04m

C$ 419

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 9/10

6:00 a.m.-12:33 p.m.

1 stop7h 33m

Chicago Midway

Mon 19/10

6:30 p.m.-11:00 p.m.

1 stop3h 30m

C$ 440

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 31/7

12:09 p.m.-6:25 p.m.

1 stop7h 16m

Chicago Midway

Sun 2/8

9:19 a.m.-5:24 p.m.

1 stop7h 05m

C$ 449

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/6

Showing 1-10 of 23 resultsSorted by cheapest first
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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 much does it cost to fly round-trip from Toronto Pearson Intl Airport to Chicago Midway Airport?

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 22 June 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
438 reviews
Check prices

Food

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

6.9

Overall

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Porter Airlines
8.0
Very good
438 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Food

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

6.9

Overall

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

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 4h 07m. 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$ 116 on this airline. This flight start at 76% 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 O'Hare Intl flights
Toronto Island to Midway 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 22 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 116AverageC$ 326FlexibilityNo 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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