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Cheap flights from Toronto Island Airport to Chicago Midway Airport from C$ 146

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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — MDW
19 Aug — 26 Aug1
1 adult

Cheap 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 14 August 2025.

Round-trip from

C$ 240

One-way from

C$ 146

Popular in

November

Cheapest in

July

Average price

C$ 299

Good round-trip deal

C$ 216 or less

Good one-way deal

C$ 128 or less
Porter Airlines
  • Porter Airlines
  • 5/9-7/9
  • Nonstop
  • 3h 31m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 8/9
  • Nonstop
  • 1h 49m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 17% potential increase in price (C$ 93 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 14 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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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Find flight deals from Toronto Island to Midway

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 14 August 2025.

Fri 5/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 8/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 240
Fri 26/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Tue 30/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/8C$ 241
Thu 2/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 5/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 243
Wed 3/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Tue 23/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/8C$ 247
Fri 19/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 21/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/8C$ 248
Sat 6/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 7/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 250
Wed 3/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 15/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/8C$ 251
Sun 7/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Wed 10/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 252
Fri 26/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 26/1011:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 254
Thu 30/109:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 4/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 255

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 14 August 2025.
Use the filters below to find and compare flights from Toronto Island Airport to Chicago Midway Airport that are best for you.

Fly from

Toronto Island

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 2/10

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Sun 5/10

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Mon 8/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Sun 7/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 27/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sat 4/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 26/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Fri 3/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 26/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Tue 30/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 10/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Wed 17/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 24/10

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Sun 26/10

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

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 13/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sat 20/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 12/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Fri 19/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 241

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/8

Showing 1-10 of 21 results
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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 month to book a flight from Toronto Island Airport to Chicago Midway Airport?

Currently, June is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of C$ 233). Flying from Toronto Island Airport to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 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 14 August 2025.

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 31% versus a flight in the afternoon.

Weekly flight availability from Toronto Island Airport to Chicago Midway Airport

Explore weekly flight availability from Toronto Island to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 14 August 2025.

The most flights from YTZ to MDW are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

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 14 August 2025.
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
332 reviews
Check prices

Crew

8.7

Food

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
332 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Crew

8.7

Food

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

  • 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$ 202), offers the cheapest pricing from Toronto Island Airport to Chicago Midway Airport. Porter Airlines is priced at 37% 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 (82%), Porter Airlines (82%) or Air Transat (82%) 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$ 203 for a flight from Toronto Island Airport to Chicago Midway Airport. The cheapest flight overall is C$ 123 while the most popular route, (Toronto Island - Chicago Midway) is currently priced at C$ 240.

  • 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.

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

    Currently, June is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of C$ 233). Flying from Toronto Island Airport to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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

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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
Region of Waterloo Intl to O'Hare Intl flights
Hamilton 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 14 August 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 202AverageC$ 320FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

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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.

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