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Cheap flights from Chicago Midway Airport to Toronto from C$ 139

MDW — YTO
9 Oct — 16 Oct1
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

Mon 28/93:20 p.m. -
Nonstop1h 40m
Tue 29/910:10 a.m. -
Nonstop1h 50m
Deal found 7/9C$ 316
Tue 29/911:45 a.m. -
Nonstop1h 40m
Sun 4/1010:10 a.m. -
Nonstop1h 50m
Deal found 8/9C$ 317
Mon 28/93:20 p.m. -
Nonstop1h 40m
Wed 30/910:10 a.m. -
Nonstop1h 50m
Deal found 8/9C$ 319
Sat 26/911:45 a.m. -
Nonstop1h 40m
Mon 28/910:10 a.m. -
Nonstop1h 50m
Deal found 4/9C$ 320
Thu 24/911:45 a.m. -
Nonstop1h 40m
Tue 6/101:45 p.m. -
Nonstop1h 50m
Deal found 8/9C$ 321
Tue 29/911:45 a.m. -
Nonstop1h 40m
Fri 2/1010:10 a.m. -
Nonstop1h 50m
Deal found 6/9C$ 323
Thu 1/103:20 p.m. -
Nonstop1h 40m
Sun 4/1010:10 a.m. -
Nonstop1h 50m
Deal found 8/9C$ 328
Wed 21/103:20 p.m. -
Nonstop1h 40m
Sat 24/101:45 p.m. -
Nonstop1h 50m
Deal found 8/9C$ 330
Thu 24/911:45 a.m. -
Nonstop1h 40m
Wed 30/91:45 p.m. -
Nonstop1h 50m
Deal found 8/9C$ 339
Fri 23/103:20 p.m. -
Nonstop1h 40m
Sat 24/101:45 p.m. -
Nonstop1h 50m
Deal found 7/9C$ 343
Sun 4/1011:45 a.m. -
Nonstop1h 40m
Sat 10/101:45 p.m. -
Nonstop1h 50m
Deal found 5/9C$ 346
Thu 8/109:29 a.m. -
1 stop6h 50m
Sun 11/106:00 a.m. -
1 stop4h 32m
Deal found 5/9C$ 370

Find flight deals from Midway to Toronto

Round-trip from

C$ 316

One-way from

C$ 139

Popular in

August

Cheapest in

January

Average price

C$ 337

Good round-trip deal

C$ 329 or less

Good one-way deal

C$ 199 or less
Air Transat
  • Air Transat
  • 28/9-29/9
  • Nonstop
  • 3h 30m total
  • Chicago to Toronto
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Porter Airlines
  • Porter Airlines
  • 30/9-31/12
  • Nonstop
  • 1h 40m total
  • Chicago to Toronto
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Highest demand for flights based on searches. 8% potential increase in price (C$ 48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 18 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Price to beat on a round-trip flight from Chicago Midway to Toronto (YTO).
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Price to beat on a one-way flight from Chicago Midway to Toronto (YTO).
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Cheapflights Fare Finder

 
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 Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Wed 30/9

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

Nonstop1h 40m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 139

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Sat 10/10

1:27 p.m.-10:56 p.m.

1 stop8h 29m

Toronto Pearson Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 145

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Sat 10/10

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 145

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Sat 24/10

1:27 p.m.-10:56 p.m.

1 stop8h 29m

Toronto Pearson Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 145

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Sun 22/11

1:31 p.m.-10:57 p.m.

1 stop8h 26m

Toronto Pearson Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 145

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Fri 23/10

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

Nonstop1h 40m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 152

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Mon 5/10

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

Nonstop1h 40m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 152

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Sat 3/10

6:40 p.m.-10:59 p.m.

1 stop3h 19m

Toronto Pearson Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 152

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Thu 1/10

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

Nonstop1h 40m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 152

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Wed 4/11

6:44 p.m.-10:56 p.m.

1 stop3h 12m

Toronto Pearson Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 152

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

Showing 1-10 of 44 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

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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto (average of C$ 283). Flying from Chicago Midway Airport to Toronto in February is currently the most expensive (average of C$ 905). 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?

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.

Weekly flight availability from Chicago Midway Airport to Toronto

The most flights from MDW to YTO are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

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

Airfare is typical for this route at the moment.
Chicago Midway Airport to Toronto flights typically cost between C$ 306 and C$ 572 in September.
The cheapest round-trip price found within the last 5 days was C$ 316 on Multiple Airlines (28 Sep-29 Sep).

How often are flights from Chicago to Toronto delayed?

About 15% of weekly flights between Chicago and Toronto have experienced delays in the past year, with the average delay time being 111 minutes.

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

Historically, flights departing in the evening 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?

Saturday tends to have the lowest number of delays on this route, whereas Tuesday 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 15% of flights being delayed.

Reviews of airlines servicing Toronto

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
458 reviews
Check prices

Crew

8.6

Food

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Porter Airlines
8.0
Very good
458 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Crew

8.6

Food

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

Related info for your journey

  • 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 20m. 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto (average of C$ 283). Flying from Chicago Midway Airport to Toronto in February is currently the most expensive (average of C$ 905). 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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