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

MDW — YTZ
9 Oct — 16 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Midway to Toronto Island

Enter your travel dates to find the best prices.

Cheapest flights from Midway to Toronto Island

Mon 28/911:45 a.m. -
Nonstop1h 40m
Fri 2/1010:10 a.m. -
Nonstop1h 50m
Deal found 9/9C$ 306
Fri 9/103:20 p.m. -
Nonstop1h 40m
Mon 12/101:45 p.m. -
Nonstop1h 50m
Deal found 9/9C$ 310
Fri 9/103:20 p.m. -
Nonstop1h 40m
Sun 11/101:45 p.m. -
Nonstop1h 50m
Deal found 9/9C$ 313
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$ 318
Thu 24/911:45 a.m. -
Nonstop1h 40m
Mon 5/1010:10 a.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

Find flight deals from Midway to Toronto Island

Round-trip from

C$ 316

One-way from

C$ 139

Popular in

February

Cheapest in

April

Average price

C$ 306

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
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 126 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease (C$ 49 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 Island.
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Price to beat on a one-way flight from Chicago Midway to Toronto Island.
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Chicago Midway Airport to Toronto Island Airport 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 - 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 - 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 - 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 - 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

Fri 9/10

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$ 208

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Thu 8/10

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$ 210

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Fri 2/10

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$ 245

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Wed 4/11

6:16 a.m.-12:52 p.m.

2 stops29h 36m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 291

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Thu 1/10

12:54 p.m.-4:00 p.m.

2 stops26h 06m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 295

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

Showing 1-10 of 22 resultsSorted by cheapest first
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Best time to book a flight from Midway to Toronto Island

Have a flexible travel schedule? Discover the best time to fly to Toronto Island 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 Island Airport

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

Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto Island Airport (average of C$ 270). Flying from Chicago Midway Airport to Toronto Island Airport in February is currently the most expensive (average of C$ 904). 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 YTZ?

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 Island Airport as you normally would.

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

Airfare is typical for this route at the moment.

Chicago Midway Airport to Toronto Island Airport flights typically cost between C$ 283 and C$ 372 in September.
The cheapest round-trip price found within the last 5 days was C$ 316 on Multiple Airlines (28 Sep-29 Sep).

Related info for your journey

  • How long is the flight from Chicago Midway Airport to Toronto Island Airport?

    Porter Airlines can get you from Chicago Midway Airport to Toronto Island Airport in just under 1h 40m. Your travel time will be generally consistent. The distance from Chicago Midway Airport to Toronto Island Airport is about 711 km. All flights are typically direct.

  • What are the most reliable airlines from Chicago Midway Airport to Toronto Island Airport?

    Before booking your flight to Toronto Island Airport from Chicago Midway Airport, check out the most reliable airlines to get you to your destination on time: Porter Airlines (65%), Porter Airlines (65%), Air Transat( 65%).

  • What are the cheapest flights from Chicago Midway Airport to Toronto Island Airport?

    The cheapest flight price from Chicago Midway Airport to Toronto Island Airport is C$ 185. On average you can expect to pay C$ 331. The most popular route, (Chicago Midway - Toronto Island), can usually be booked for C$ 278.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto Island Airport (average of C$ 270). Flying from Chicago Midway Airport to Toronto Island Airport in February is currently the most expensive (average of C$ 904). 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Midway to Toronto Island

O'Hare Intl to Pearson Intl flights
O'Hare Intl to Toronto Island flights
Midway to Pearson Intl flights
O'Hare Intl to Hamilton flights

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Why should you use Cheapflights to find cheap flight tickets from Midway to Toronto Island?

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