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Cheap flights from Toronto Island Airport to Chicago Midway Airport from C$ 154

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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — MDW
11 Oct — 18 Oct1
1 adult
1 adult, Economy

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 11 September 2025.

Round-trip from

C$ 238

One-way from

C$ 154

Popular in

November

Cheapest in

July

Average price

C$ 342

Good round-trip deal

C$ 243 or less

Good one-way deal

C$ 226 or less
Porter Airlines
  • Porter Airlines
  • 24/10-27/10
  • Nonstop
  • 3h 31m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 9/11
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 16% potential increase in price (C$ 86 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 September 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 11 September 2025.

Fri 24/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 27/1011:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/9C$ 238
Wed 15/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Wed 15/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/9C$ 240
Tue 30/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Tue 7/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/9C$ 247
Fri 3/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 5/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/9C$ 248
Fri 3/107:50 a.m.YTZ - MDW
Nonstop1h 49mAir Transat
Mon 6/109:35 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 9/9C$ 256
Mon 27/102:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 3/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/9C$ 261
Fri 24/107:50 a.m.YTZ - MDW
Nonstop1h 49mAir Transat
Mon 27/104:15 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 9/9C$ 273
Wed 8/107:50 a.m.YTZ - MDW
Nonstop1h 49mAir Transat
Sun 19/109:35 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 8/9C$ 274
Sat 25/107:50 a.m.YTZ - MDW
Nonstop1h 49mMultiple Airlines
Sat 1/1112:45 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 10/9C$ 276
Fri 24/103:35 p.m.YTZ - MDW
Nonstop1h 49mMultiple Airlines
Sun 26/104:15 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 9/9C$ 279
Fri 3/107:50 a.m.YTZ - MDW
Nonstop1h 49mMultiple Airlines
Tue 7/105:20 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 9/9C$ 280
Sun 26/102:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 30/1011:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/9C$ 281

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 11 September 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

Wed 15/10

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

Nonstop1h 49m

Chicago Midway

Wed 15/10

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

Nonstop1h 42m

C$ 240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 7/10

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

Nonstop1h 49m

Chicago Midway

Tue 14/10

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

Nonstop1h 42m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 27/10

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

Nonstop1h 50m

Chicago Midway

Mon 3/11

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 14/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 16/11

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

Nonstop1h 42m

C$ 273

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Mon 8/12

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 280

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 26/10

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

Nonstop1h 50m

Chicago Midway

Thu 30/10

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

Nonstop1h 42m

C$ 281

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 23/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 30/11

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

Nonstop1h 42m

C$ 283

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 25/10

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

Nonstop1h 49m

Chicago Midway

Sat 1/11

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

C$ 285

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 24/10

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

Nonstop1h 49m

Chicago Midway

Mon 27/10

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

Nonstop1h 42m

C$ 290

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 14/10

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

Nonstop1h 49m

Chicago Midway

Fri 17/10

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

Nonstop1h 42m

C$ 295

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 22 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, September is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of C$ 209). 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 11 September 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 21% versus a flight at noon.

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 11 September 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
7.9
Good
363 reviews
Check prices

Boarding

8.1

Entertainment

7.0

Overall

7.9

Food

7.6

Comfort

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Boarding

8.1

Entertainment

7.0

Overall

7.9

Food

7.6

Comfort

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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$ 240, Porter Airlines can have you in Chicago Midway Airport from Toronto Island Airport in 1h 49m. 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$ 205), 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%), Air Transat (82%) or Porter Airlines (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$ 334 for a flight from Toronto Island Airport to Chicago Midway Airport. The cheapest flight overall is C$ 147 while the most popular route, (Toronto Island - Chicago Midway) is currently priced at C$ 218.

  • 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, September is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of C$ 209). 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

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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 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 205AverageC$ 319FlexibilityNo 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.

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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.

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