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Cheap flights from Chicago Midway Airport to Toronto from C$ 171

MDW — YTO
23 Nov — 30 Nov1
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

Thu 12/119:30 a.m. -
1 stop6h 50m
Mon 16/1112:15 p.m. -
1 stop6h 49m
Deal found 21/10C$ 400
Thu 12/111:31 p.m. -
1 stop8h 26m
Wed 25/1112:15 p.m. -
1 stop6h 49m
Deal found 21/10C$ 423
Fri 18/121:41 p.m. -
1 stop8h 26m
Tue 5/112:15 p.m. -
1 stop7h 22m
Deal found 22/10C$ 424
Fri 13/119:30 a.m. -
1 stop6h 50m
Sun 15/116:00 a.m. -
1 stop4h 46m
Deal found 22/10C$ 454
Sat 21/111:31 p.m. -
1 stop8h 26m
Sat 28/1112:15 p.m. -
1 stop6h 49m
Deal found 23/10C$ 456
Fri 4/126:41 p.m. -
1 stop3h 26m
Fri 11/1212:15 p.m. -
1 stop6h 46m
Deal found 20/10C$ 468
Wed 11/119:30 a.m. -
1 stop3h 00m
Fri 13/1112:15 p.m. -
1 stop6h 49m
Deal found 21/10C$ 469
Wed 11/119:30 a.m. -
1 stop6h 50m
Mon 30/116:00 a.m. -
1 stop7h 51m
Deal found 21/10C$ 476
Thu 26/1112:05 p.m. -
1 stop4h 15m
Sun 29/1112:15 p.m. -
1 stop6h 49m
Deal found 19/10C$ 489
Thu 19/119:30 a.m. -
1 stop3h 00m
Sun 22/1112:15 p.m. -
1 stop6h 49m
Deal found 20/10C$ 503
Fri 11/125:02 p.m. -
2 stops18h 48m
Mon 14/124:15 p.m. -
2 stops20h 18m
Deal found 23/10C$ 524
Thu 22/103:20 p.m. -
Nonstop1h 40m
Fri 23/1010:10 a.m. -
Nonstop1h 50m
Deal found 21/10C$ 531

Find flight deals from Midway to Toronto

Round-trip from

C$ 400

One-way from

C$ 171

Popular in

August

Cheapest in

January

Average price

C$ 400

Good round-trip deal

C$ 514 or less

Good one-way deal

C$ 239 or less
KLM
  • KLM
  • 12/11-16/11
  • 2 total stops
  • 13h 39m total
  • Chicago to Toronto
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Delta
  • Delta
  • 25/11-31/12
  • 1 total stop
  • 3h 00m total
  • Chicago to Toronto
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 112 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 October 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

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Wed 21/4

1:00 p.m.-5:22 p.m.

1 stop3h 22m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 171

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Mon 16/11

6:08 a.m.-12:50 p.m.

2 stops29h 42m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 185

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Tue 5/1

1:00 p.m.-7:07 p.m.

1 stop5h 07m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 186

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Fri 1/1

6:15 p.m.-10:59 p.m.

1 stop3h 44m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 186

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Sat 14/11

6:44 p.m.-10:57 p.m.

1 stop3h 13m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 186
Quickest round-trip

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Wed 25/11

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

1 stop3h 00m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 186

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Sat 13/2

9:30 a.m.-4:04 p.m.

1 stop5h 34m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 186

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Thu 3/12

5:02 p.m.-12:50 p.m.

2 stops42h 48m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 192

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Sun 29/11

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

1 stop3h 00m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 195

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Fri 18/12

1:41 p.m.-11:07 p.m.

1 stop8h 26m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 195

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/10

Showing 1-10 of 37 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$ 287). Flying from Chicago Midway Airport to Toronto in February is currently the most expensive (average of C$ 918). 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.

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

Airfare is below average for this route at the moment.
Chicago Midway Airport to Toronto flights typically cost between C$ 405 and C$ 463 in November.
The cheapest round-trip price found within the last 5 days was C$ 400 on KLM (12 Nov-16 Nov).

How often are flights from Chicago to Toronto delayed?

About 18% of weekly flights between Chicago and Toronto have experienced delays in the past year, with the average delay time being 112 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 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 17% 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
467 reviews
Check prices

Entertainment

6.9

Crew

8.6

Food

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

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
467 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Entertainment

6.9

Crew

8.6

Food

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

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 Delta fly from Chicago Midway Airport to Toronto in about 8h 26m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 695 km.

  • 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$ 287). Flying from Chicago Midway Airport to Toronto in February is currently the most expensive (average of C$ 918). 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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