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$106+ Cheap flights from Toronto Island (YTZ) to Midway (MDW)

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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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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 August 14, 2025.

Round-trip from

$174
(SmartFares)

One-way from

$106
(SmartFares)

Popular in

November

Cheapest in

July

Average price

$217

Good round-trip deal

$174 or less

Good one-way deal

$109 or less
From Toronto Island to Chicago Midway
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One-way flight from Toronto Island to Chicago Midway
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Highest demand for flights based on searches. 17% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($7 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 August 14, 2025.

This SmartFares deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/37:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Tue 10/75:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/14$174
This SmartFares deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/103:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Wed 9/175:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/12$175
This Mytrip deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/23:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 10/55:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/14$176
This SmartFares deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/33:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 10/59:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/14$179
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/193:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 9/219:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/13$180
This KAYAK deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/137:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Thu 10/165:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/13$182
This FlightHub deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/67:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 9/79:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/14$183
This SmartFares deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 10/205:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/13$184
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/193:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 9/225:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/13$185

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 2,558,603 searches. Data last updated August 14, 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 9/18

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Sun 9/28

9:35 am-12:17 pm

Nonstop1h 42m

$174

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 10/3

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Tue 10/7

5:20 pm-8:02 pm

Nonstop1h 42m

$174

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 9/10

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Sat 9/20

9:35 am-12:17 pm

Nonstop1h 42m

$174

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 9/27

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Sat 10/4

9:35 am-12:17 pm

Nonstop1h 42m

$174

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 9/26

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Mon 9/29

9:35 am-12:17 pm

Nonstop1h 42m

$174

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 10/3

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Mon 10/6

5:20 pm-8:02 pm

Nonstop1h 42m

$174

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 9/26

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Tue 9/30

5:20 pm-8:02 pm

Nonstop1h 42m

$175

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 9/10

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Wed 9/17

5:20 pm-8:02 pm

Nonstop1h 42m

$175

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 9/13

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Sat 9/20

9:35 am-12:17 pm

Nonstop1h 42m

$175

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 9/12

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Fri 9/19

5:20 pm-8:02 pm

Nonstop1h 42m

$175

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

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, April is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of $160). Flying from Toronto Island Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 August 14, 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 at noon, which can drop the price by up to 12% 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 August 14, 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 August 14, 2025.
Read through reviews of airlines operating flights from Toronto Island Airport to Chicago Midway Airport, such as Porter Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
332 reviews

Crew

8.7

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.0

Food

7.6

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

Crew

8.7

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.0

Food

7.6

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?

    Porter Airlines, at $158, was found to be the cheapest airline from Toronto Island Airport to Chicago Midway Airport.. Porter Airlines is currently priced 32% below the average price you’ll pay for this route.

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

    The top 3 most reliable airlines when flying from Toronto Island Airport to Chicago Midway Airport are Porter Airlines (82%), Porter Airlines (82%) and Air Transat (82%).

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

    The cheapest flight price from Toronto Island Airport to Chicago Midway Airport is $93. On average you can expect to pay $219. The most popular route, (Toronto Island - Chicago Midway), can usually be booked for $174.

  • 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, April is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of $160). Flying from Toronto Island Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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

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 2,558,603 searches. Data last updated August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$257FlexibilityNo cancel feeOn-time52%

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