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Cheap flights from Chicago Midway Airport to Toronto Island Airport from C$ 182

MDW — YTZ
24 Nov — 1 Dec1
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

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
Fri 11/125:02 p.m. -
2 stops18h 48m
Tue 15/127:10 p.m. -
2 stops17h 23m
Deal found 23/10C$ 567
Thu 3/123:36 p.m. -
2 stops20h 14m
Mon 7/127:10 p.m. -
2 stops17h 23m
Deal found 20/10C$ 569
Thu 12/116:08 a.m. -
3 stops36h 47m
Thu 19/117:35 a.m. -
2 stops11h 12m
Deal found 23/10C$ 598
Sat 14/117:15 a.m. -
2 stops28h 35m
Mon 16/119:10 a.m. -
3 stops15h 37m
Deal found 19/10C$ 602
Tue 8/1212:28 p.m. -
2 stops20h 11m
Tue 15/129:10 a.m. -
2 stops25h 35m
Deal found 24/10C$ 604
Fri 11/125:02 p.m. -
2 stops18h 48m
Sun 13/124:15 p.m. -
2 stops18h 30m
Deal found 23/10C$ 623
Fri 13/116:42 p.m. -
2 stops20h 12m
Mon 16/114:15 p.m. -
3 stops20h 07m
Deal found 22/10C$ 626

Find flight deals from Midway to Toronto Island

Round-trip from

C$ 524

One-way from

C$ 182

Popular in

February

Cheapest in

April

Average price

C$ 465

Good round-trip deal

C$ 514 or less

Good one-way deal

C$ 239 or less
11/12-14/12
  • 11/12-14/12
  • 4 total stops
  • 39h 06m total
  • Chicago to Toronto
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9/11-31/12
  • 9/11-31/12
  • 2 total stops
  • 41h 08m total
  • Chicago to Toronto
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 62 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease (C$ 50 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 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

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 - 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 - YTZ Toronto Island

MDWYTZ

Chicago Midway

Tue 26/1

1:18 p.m.-12:52 p.m.

2 stops22h 34m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 206

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Mon 7/12

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$ 218

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Sat 14/11

7:15 a.m.-12:50 p.m.

3 stops28h 35m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 272
Quickest round-trip

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Sun 10/1

5:21 p.m.-12:52 p.m.

2 stops18h 31m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 272

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Sat 13/2

1:18 p.m.-12:52 p.m.

2 stops22h 34m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 342

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Thu 5/11

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

3 stops29h 42m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 346

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Mon 21/12

1:11 p.m.-12:50 p.m.

2 stops22h 39m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 382

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Fri 6/11

8:09 p.m.-6:29 p.m.

2 stops21h 20m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 409

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/10

Showing 1-10 of 18 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$ 274). Flying from Chicago Midway Airport to Toronto Island Airport in February is currently the most expensive (average of C$ 919). 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 below average for this route at the moment.

Chicago Midway Airport to Toronto Island Airport flights typically cost between C$ 622 and C$ 650 in December.
The cheapest round-trip price found within the last 5 days was C$ 524 on Multiple Airlines (11 Dec-14 Dec).

Related info for your journey

  • 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 (71%), Porter Airlines (71%), Air Transat( 71%).

  • 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$ 239. On average you can expect to pay C$ 446. The most popular route, (Chicago Midway - Toronto Island), can usually be booked for C$ 510.

  • 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$ 274). Flying from Chicago Midway Airport to Toronto Island Airport in February is currently the most expensive (average of C$ 919). 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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Can Cheapflights find flights from Midway to Toronto Island with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Midway to Toronto Island, users can toggle the no change fees filter when performing a flight search.

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