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Cheap flights from Toronto Island Airport to Chicago Midway Airport from C$ 166

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 25/6. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — MDW
4 May — 11 May1
1 adult

Cheapflights Tip: The best prices from Toronto Island to Chicago Midway are usually found in March or January, booked 23 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

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 29 April 2025.

Round-trip from

C$ 244

One-way from

C$ 166

Popular in

November

Cheapest in

March

Average price

C$ 336

Good round-trip deal

C$ 264 or less

Good one-way deal

C$ 151 or less
Porter Airlines
  • Porter Airlines
  • 22/5-26/5
  • Nonstop
  • 3h 31m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 25/6
  • Nonstop
  • 1h 49m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 9% potential increase in price (C$ 53 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 10 potential savings vs. average RT price).
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Average for round-trip flights in April 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 29 April 2025.

Wed 28/57:30 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Wed 4/65:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 29/4C$ 244
Fri 13/67:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Fri 20/65:50 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 29/4C$ 248
Thu 28/87:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Mon 1/99:15 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 28/4C$ 249

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 29 April 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 28/5

7:30 a.m.-8:19 a.m.

Nonstop1h 49m

Chicago Midway

Wed 4/6

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

Nonstop1h 42m

C$ 244

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 13/6

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Fri 20/6

5:50 p.m.-8:32 p.m.

Nonstop1h 42m

C$ 248

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 28/8

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Mon 1/9

9:15 a.m.-11:57 a.m.

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 25/6

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

Nonstop1h 49m

C$ 166

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 2/8

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

C$ 183

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/8

8:45 a.m.-5:35 p.m.

1 stop9h 50m

C$ 291

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/4

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

How far ahead should I book a flight from Toronto Island Airport to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Toronto Island to Midway. Price data was last updated on 25 April 2025.

To ensure you get the cheapest price possible for a flight from Toronto Island Airport to Chicago Midway Airport, you should look to book at least 23 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, January is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of C$ 243). 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 29 April 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 7% versus a flight in the afternoon.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 43.0 mm.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 29 April 2025.
Read through reviews of airlines operating flights from Toronto to Chicago, such as Porter Airlines and Air Transat. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
285 reviews
Check prices

Entertainment

7.0

Comfort

8.1

Overall

8.0

Crew

8.8

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Entertainment

7.0

Comfort

8.1

Overall

8.0

Crew

8.8

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Transat
7.8
Good
385 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Entertainment

7.0

Comfort

8.1

Overall

8.0

Crew

8.8

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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 are the cheapest airlines flying from Toronto Island Airport to Chicago Midway Airport round-trip?

    According to our current data, Porter Airlines (C$ 244), and Air Transat (C$ 248) offers the cheapest pricing from Toronto Island Airport to Chicago Midway Airport. Porter Airlines is priced at 31% 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 (83%), Porter Airlines (83%) or Air Transat (83%) 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$ 235 for a flight from Toronto Island Airport to Chicago Midway Airport. The cheapest flight overall is C$ 145 while the most popular route, (Toronto Island - Chicago Midway) is currently priced at C$ 180.

  • 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, January is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of C$ 243). 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.
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Pearson Intl to Midway flights
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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 29 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 267AverageC$ 361FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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

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