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Cheap flights from Chicago Midway Airport to Toronto from C$ 125

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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YTO
25 May — 1 Jun1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Midway to Toronto

Enter your travel dates to find the best prices.

Cheapest flights from Midway to Toronto
Explore the most affordable flight options available from Midway to Toronto. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 25 April 2026.

Wed 15/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Mon 20/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 22/4C$ 292
Thu 23/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Mon 27/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 22/4C$ 294
Fri 31/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Thu 6/88:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 21/4C$ 297
Thu 6/83:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Thu 13/81:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 20/4C$ 300
Sun 16/810:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Thu 27/81:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 22/4C$ 301
Fri 8/510:30 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Tue 16/68:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 23/4C$ 302
Fri 15/53:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sun 17/58:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 20/4C$ 304
Fri 7/810:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Mon 10/88:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 20/4C$ 305
Fri 8/510:30 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Tue 12/58:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 23/4C$ 307
Mon 4/510:30 a.m.
MDW
-
YTZ
Nonstop1h 40m
Multiple Airlines
Wed 6/58:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 20/4C$ 308
Thu 28/510:30 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sat 30/58:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 23/4C$ 309
Fri 15/53:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Wed 20/58:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 20/4C$ 311

Find flight deals from Midway to Toronto

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Toronto (YTO). 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 25 April 2026.

Round-trip from

C$ 292

One-way from

C$ 125

Popular in

June

Cheapest in

July

Average price

C$ 312

Good round-trip deal

C$ 328 or less

Good one-way deal

C$ 133 or less
Porter Airlines
  • Porter Airlines
  • 15/7-20/7
  • Nonstop
  • 3h 30m total
  • Chicago to Toronto
Search Deals
Porter Airlines
  • Porter Airlines
  • 12/5
  • Nonstop
  • 1h 40m total
  • Chicago to Toronto
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (C$ 7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Toronto (YTO).
Search Deals
Price to beat on a one-way flight from Chicago Midway to Toronto (YTO).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Toronto 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 25 April 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Toronto that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 8/5

10:30 a.m.-1:10 p.m.

Nonstop1h 40m

Toronto Island

Sun 10/5

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

C$ 302

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 15/7

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Mon 20/7

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 319

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 14/5

10:30 a.m.-1:10 p.m.

Nonstop1h 40m

Toronto Island

Sun 17/5

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

C$ 322

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 4/6

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Mon 8/6

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 345

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 14/5

9:22 a.m.-1:30 p.m.

1 stop3h 08m

Toronto Pearson Intl

Tue 26/5

6:10 a.m.-12:42 p.m.

1 stop7h 32m

C$ 356

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 15/5

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

1 stop8h 08m

Toronto Pearson Intl

Sun 24/5

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

1 stop7h 24m

C$ 356

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 2/6

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

1 stop6h 59m

Toronto Pearson Intl

Sun 14/6

6:10 a.m.-9:14 a.m.

1 stop4h 04m

C$ 356

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 11/5

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

1 stop6h 59m

Toronto Pearson Intl

Wed 20/5

12:29 p.m.-5:56 p.m.

1 stop6h 27m

C$ 357

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 13/6

6:35 p.m.-11:02 p.m.

1 stop3h 27m

Toronto Pearson Intl

Sat 20/6

6:10 a.m.-9:14 a.m.

1 stop4h 04m

C$ 357

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 3/6

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

1 stop3h 23m

Toronto Pearson Intl

Sun 7/6

6:10 a.m.-9:14 a.m.

1 stop4h 04m

C$ 357

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/4

Showing 1-10 of 38 resultsSorted by cheapest first
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Best time to book a flight from Midway to Toronto

Have a flexible travel schedule? Discover the best time to fly to Toronto from Midway 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 Chicago Midway Airport to Toronto

What is the cheapest month to book a flight from Chicago Midway Airport to Toronto?

Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto (average of C$ 79). Flying from Chicago Midway Airport to Toronto in October is currently the most expensive (average of C$ 272). 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 MDW to YTO?

Find hourly flight availability from Midway to Toronto. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 25 April 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Toronto as you normally would.

How much does it cost to fly round-trip from Chicago Midway Airport to Toronto?

How often are flights from Chicago to Toronto delayed?

About 14% of weekly flights between Chicago and Toronto have experienced delays in the past year, with the average delay time being 117 minutes.

What is the most punctual flight time for Chicago to Toronto 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?

Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Toronto flights?

Over the past year, Porter Airlines has had the lowest number of delays on this route, with just 13% of flights being delayed.

Reviews of airlines servicing Toronto

Get insights into the airlines that provide service to Toronto. 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 Toronto. Reviews last updated 25 April 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Toronto, such as Porter Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
435 reviews
Check prices

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Crew

8.6

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
435 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Crew

8.6

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 Midway to Toronto. 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 Chicago Midway Airport to Toronto?

    Airlines like Porter Airlines and Delta fly from Chicago Midway Airport to Toronto in about 1h 40m. The time it takes to get you to your destination can typically vary by up to 1h 28m. Airlines will cover a distance of 711 km. Both multi-stop and direct flights can be found to your destination and back.

  • Can I find deals for flights from Midway to Toronto that include hotel bookings?

    Yes. In addition to deals on Midway to Toronto flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Toronto?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Toronto.

  • Can I find deals for business class flights from Midway to Toronto?

    Yes. Cheapflights offers flight deals from Midway to Toronto 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 Chicago Midway Airport to Toronto?

    Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto (average of C$ 79). Flying from Chicago Midway Airport to Toronto in October is currently the most expensive (average of C$ 272). 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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Why should you use Cheapflights to find cheap flight tickets from Midway to Toronto?

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