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Cheap flights from Toronto Island Airport to Chicago Midway Airport from C$ 189

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

Cheap flight deals from Toronto Island to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Toronto Island to Midway

Fri 18/91:45 p.m. -
Nonstop1h 50m
Sun 20/911:45 a.m. -
Nonstop1h 40m
Deal found 28/8C$ 298
Sat 17/101:45 p.m. -
Nonstop1h 50m
Sun 18/103:20 p.m. -
Nonstop1h 40m
Deal found 2/9C$ 301
Thu 24/910:10 a.m. -
Nonstop1h 50m
Sun 27/911:45 a.m. -
Nonstop1h 40m
Deal found 31/8C$ 303
Sat 26/910:10 a.m. -
Nonstop1h 50m
Sun 27/911:45 a.m. -
Nonstop1h 40m
Deal found 30/8C$ 305
Fri 18/91:45 p.m. -
Nonstop1h 50m
Mon 21/93:20 p.m. -
Nonstop1h 40m
Deal found 28/8C$ 307
Mon 21/91:45 p.m. -
Nonstop1h 50m
Wed 30/911:45 a.m. -
Nonstop1h 40m
Deal found 28/8C$ 310
Sat 19/910:10 a.m. -
Nonstop1h 50m
Sun 20/911:45 a.m. -
Nonstop1h 40m
Deal found 29/8C$ 315
Tue 29/910:10 a.m. -
Nonstop1h 50m
Tue 6/1011:45 a.m. -
Nonstop1h 40m
Deal found 30/8C$ 316
Sat 19/910:10 a.m. -
Nonstop1h 50m
Wed 23/93:20 p.m. -
Nonstop1h 40m
Deal found 31/8C$ 318
Wed 14/1010:10 a.m. -
Nonstop1h 50m
Sun 18/103:20 p.m. -
Nonstop1h 40m
Deal found 1/9C$ 319
Wed 23/910:10 a.m. -
Nonstop1h 50m
Thu 24/93:20 p.m. -
Nonstop1h 40m
Deal found 29/8C$ 321
Sat 26/91:45 p.m. -
Nonstop1h 50m
Sat 3/1011:45 a.m. -
Nonstop1h 40m
Deal found 29/8C$ 325

Find flight deals from Toronto Island to Midway

Round-trip from

C$ 298

One-way from

C$ 189

Popular in

June

Cheapest in

January

Average price

C$ 512

Good round-trip deal

C$ 293 or less

Good one-way deal

C$ 286 or less
Air Transat
  • Air Transat
  • 18/9-20/9
  • Nonstop
  • 3h 30m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 25/9
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 109 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 27 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 Toronto Island to Chicago Midway.
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Price to beat on a one-way flight from Toronto Island to Chicago Midway.
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Toronto Island Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 29/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Sat 3/10

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

Nonstop1h 40m

C$ 318

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 23/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Thu 24/9

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

Nonstop1h 40m

C$ 321

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 27/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Sun 27/9

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

Nonstop1h 40m

C$ 329

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 28/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Mon 5/10

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

Nonstop1h 40m

C$ 355

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 25/9

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

Nonstop1h 50m

Chicago Midway

Fri 2/10

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

Nonstop1h 40m

C$ 360

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 13/10

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Thu 15/10

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

Nonstop1h 40m

C$ 365

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 27/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Thu 1/10

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

Nonstop1h 40m

C$ 418

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 17/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Mon 21/9

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

Nonstop1h 40m

C$ 418

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 2/10

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Mon 5/10

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

Nonstop1h 40m

C$ 432
Cheapest one-way
Quickest one-way

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 28/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

C$ 189

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/8

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Best time to book a flight from Toronto Island to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Toronto Island with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Toronto Island Airport to Chicago Midway Airport

What is the cheapest time of day to fly from YTZ to MDW?

When flying from Toronto Island Airport to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 50% versus a flight in the evening.

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

Airfare is typical for this route at the moment.

Toronto Island Airport to Chicago Midway Airport flights typically cost between C$ 255 and C$ 533 in September.
The cheapest round-trip price found within the last 5 days was C$ 298 on Air Transat (18 Sep-20 Sep).

Reviews of airlines servicing Midway

Check out reviews from past customers who have flown with Porter Airlines from Toronto Island Airport to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
458 reviews
Check prices

Overall

8.0

Food

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
458 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Overall

8.0

Food

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

Related info for your journey

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

    For as low as C$ 318, Porter Airlines can have you in Chicago Midway Airport from Toronto Island Airport in 1h 50m. The distance from Toronto Island Airport to Chicago Midway Airport is about 711 km. Generally, flights for this route are direct.

  • What is the cheapest airline to fly from Toronto Island Airport to Chicago Midway Airport round-trip?

    According to our current data, Porter Airlines (C$ 220), offers the cheapest pricing from Toronto Island Airport to Chicago Midway Airport. Porter Airlines is priced at 45% lower than the current average price of a flight leaving 3 months from now.

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

    No one likes to see their flight delayed. When booking a flight from Toronto Island Airport to Chicago Midway Airport consider choosing Porter Airlines (73%), Porter Airlines (73%) or Air Transat (73%) as they are the most reliable in getting you off to your destination on time.

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

    On average you can expect to pay C$ 385 for a flight from Toronto Island Airport to Chicago Midway Airport. The cheapest flight overall is C$ 153 while the most popular route, (Toronto Island - Chicago Midway) is currently priced at C$ 250.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Toronto Island to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Toronto Island to Midway

Toronto Island to O'Hare Intl flights
Pearson Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Hamilton to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights

Top airline flying from Toronto Island to Midway

AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 220AverageC$ 339FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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