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Cheap flights from Toronto Island Airport to Chicago Midway Airport from C$ 170

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 29/4. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — MDW
19 Apr — 26 Apr1
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
Explore the most affordable flight options available from Toronto Island to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 20 March 2026.

Tue 21/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 28/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 264
Sat 2/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 9/510:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 17/3C$ 265
Mon 8/61:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 10/63:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 18/3C$ 268
Sat 2/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 4/510:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/3C$ 269
Sat 11/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 18/412:55 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 270
Mon 20/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 27/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 272
Thu 23/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 27/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 273
Sat 4/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 7/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 275
Tue 7/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 8/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 16/3C$ 276
Fri 10/42:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 20/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 16/3C$ 277
Wed 8/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 12/44:05 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 15/3C$ 279
Wed 8/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 10/44:05 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 280

Find flight deals from Toronto Island to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Toronto Island (YTZ) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 20 March 2026.

Round-trip from

C$ 264

One-way from

C$ 170

Popular in

November

Cheapest in

September

Average price

C$ 275

Good round-trip deal

C$ 278 or less
Porter Airlines
  • Porter Airlines
  • 21/4-28/4
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 29/4
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 19% potential increase in price (C$ 106 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Toronto Island to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Toronto Island to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 20 March 2026.
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 - MDW

YTZMDW

Toronto Island

Sat 2/5

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Mon 4/5

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

Nonstop1h 40m

C$ 275

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 8/6

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

Nonstop1h 50m

Chicago Midway

Wed 10/6

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

Nonstop1h 40m

C$ 303

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 13/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Mon 20/4

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 306

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 30/7

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

Nonstop1h 50m

Chicago Midway

Sun 2/8

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 308

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 28/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Wed 29/4

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 308

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 17/4

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Mon 20/4

7:30 a.m.-1:20 p.m.

1 stop4h 50m

C$ 328

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 17/4

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Fri 24/4

4:05 p.m.-6:47 p.m.

Nonstop1h 42m

C$ 349
Cheapest one-way
Quickest one-way

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 28/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

C$ 185

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 10/5

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 185

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 3/5

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 185

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/3

Showing 1-10 of 19 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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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?

Find hourly flight availability from Toronto Island to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 20 March 2026.

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 in the morning, which can drop the price by up to 57% versus a flight in the evening.

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

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated 20 March 2026.
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
425 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
425 reviews
Porter Airlines
8.0
Very good
425 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

Related info for your journey

Find useful and relevant information for your journey from Toronto Island to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    For as low as C$ 275, 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$ 194), offers the cheapest pricing from Toronto Island Airport to Chicago Midway Airport. Porter Airlines is priced at 40% 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 (67%), Porter Airlines (67%) or Air Transat (67%) 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$ 347 for a flight from Toronto Island Airport to Chicago Midway Airport. The cheapest flight overall is C$ 224 while the most popular route, (Toronto Island - Chicago Midway) is currently priced at C$ 246.

  • 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

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Alternative routes for Toronto Island to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Toronto Island to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights

Top airline flying from Toronto Island to Midway

Discover the top airline that operate flights from Toronto Island to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 20 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 194AverageC$ 285FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Toronto Island to Midway?

Cheapflights makes it easy to find Toronto Island to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Toronto Island to Midway.

Can Cheapflights find flights from Toronto Island to Midway with no change fees?

Yes! Cheapflights helps users easily find flights from Toronto Island to Midway with no change fees.

Can Cheapflights notify me if prices for flights from Toronto Island to Midway become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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