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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 200

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 13/6. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
4 Jun — 11 Jun1
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 5 May 2026.

Sat 30/512:09 p.m.
YYZ
-
MDW
1 stop7h 24m
Delta
Fri 5/66:36 p.m.
MDW
-
YYZ
1 stop3h 23m
Delta
Deal found 1/5C$ 316
Fri 22/56:10 a.m.
YYZ
-
MDW
1 stop7h 32m
Delta
Tue 26/51:59 p.m.
MDW
-
YYZ
1 stop8h 15m
Delta
Deal found 30/4C$ 327
Thu 28/56:30 a.m.
YYZ
-
MDW
1 stop7h 49m
Delta
Sat 30/56:36 p.m.
MDW
-
YYZ
1 stop3h 23m
Delta
Deal found 3/5C$ 328
Fri 29/52:20 p.m.
YYZ
-
MDW
1 stop5h 13m
Delta
Sun 31/59:22 a.m.
MDW
-
YYZ
1 stop6h 59m
Delta
Deal found 30/4C$ 329
Fri 19/612:09 p.m.
YYZ
-
MDW
1 stop7h 22m
Delta
Sat 20/66:35 p.m.
MDW
-
YYZ
1 stop3h 27m
Delta
Deal found 1/5C$ 331
Fri 19/612:09 p.m.
YYZ
-
MDW
1 stop7h 22m
Delta
Sun 5/71:49 p.m.
MDW
-
YYZ
1 stop8h 25m
Delta
Deal found 30/4C$ 347
Sun 24/56:10 a.m.
YYZ
-
MDW
1 stop7h 32m
Delta
Mon 13/79:19 a.m.
MDW
-
YYZ
1 stop7h 05m
Delta
Deal found 1/5C$ 350
Tue 9/66:05 a.m.
YYZ
-
MDW
1 stop4h 09m
Delta
Thu 18/61:21 p.m.
MDW
-
YYZ
1 stop8h 41m
Delta
Deal found 30/4C$ 352
Mon 15/612:09 p.m.
YYZ
-
MDW
1 stop7h 22m
Delta
Wed 16/99:20 a.m.
MDW
-
YYZ
1 stop8h 05m
Delta
Deal found 1/5C$ 354
Fri 12/62:29 p.m.
YYZ
-
MDW
1 stop5h 02m
Delta
Sun 14/69:17 a.m.
MDW
-
YYZ
1 stop7h 07m
Delta
Deal found 1/5C$ 355
Sun 21/66:05 a.m.
YYZ
-
MDW
1 stop4h 09m
Delta
Fri 26/61:21 p.m.
MDW
-
YYZ
1 stop8h 41m
Delta
Deal found 1/5C$ 365

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 5 May 2026.

Round-trip from

C$ 316

One-way from

C$ 200

Popular in

April

Cheapest in

December

Average price

C$ 450
Delta
  • Delta
  • 30/5-5/6
  • 2 total stops
  • 10h 47m total
  • Toronto to Chicago
Search Deals
Delta
  • Delta
  • 13/6
  • 1 total stop
  • 7h 02m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 132 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 5 May 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

Mon 8/6

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

1 stop7h 39m

Chicago Midway

Mon 15/6

1:26 p.m.-11:02 p.m.

1 stop8h 36m

C$ 328

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 26/5

9:49 a.m.-12:42 p.m.

1 stop3h 53m

Chicago Midway

Fri 29/5

9:22 a.m.-5:21 p.m.

1 stop6h 59m

C$ 329

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 10/6

6:05 a.m.-9:14 a.m.

1 stop4h 09m

Chicago Midway

Mon 15/6

1:26 p.m.-11:02 p.m.

1 stop8h 36m

C$ 329
Quickest round-trip

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 29/5

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

1 stop5h 13m

Chicago Midway

Sat 30/5

6:36 p.m.-10:59 p.m.

1 stop3h 23m

C$ 329

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 28/5

12:09 p.m.-6:33 p.m.

1 stop7h 24m

Chicago Midway

Mon 1/6

9:23 a.m.-6:31 p.m.

1 stop8h 08m

C$ 329

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 29/5

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

1 stop5h 13m

Chicago Midway

Sun 31/5

9:22 a.m.-5:21 p.m.

1 stop6h 59m

C$ 329

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 16/6

6:05 a.m.-9:14 a.m.

1 stop4h 09m

Chicago Midway

Tue 23/6

1:26 p.m.-11:02 p.m.

1 stop8h 36m

C$ 329

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 31/5

12:09 p.m.-6:33 p.m.

1 stop7h 24m

Chicago Midway

Fri 5/6

9:22 a.m.-5:21 p.m.

1 stop6h 59m

C$ 329

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 15/6

12:09 p.m.-6:31 p.m.

1 stop7h 22m

Chicago Midway

Wed 16/9

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

1 stop8h 05m

C$ 354

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 26/6

6:05 a.m.-12:41 p.m.

1 stop7h 36m

Chicago Midway

Sat 27/6

1:21 p.m.-11:02 p.m.

1 stop8h 41m

C$ 369

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/4

Showing 1-10 of 21 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 5 May 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
436 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Food

7.6

Crew

8.6

Overall

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
436 reviews
Porter Airlines
8.0
Very good
436 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Food

7.6

Crew

8.6

Overall

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 7h 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 75% 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 5 May 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 112AverageC$ 384FlexibilityNo 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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