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$74+ Cheap flights from Midway (MDW) to Toronto (YTO)

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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YTO
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Midway to Toronto

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Toronto (YTO). 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

$191
(Kiwi.com)

One-way from

$74
(Kiwi.com)

Popular in

March

Cheapest in

July

Average price

$204

Good round-trip deal

$167 or less

Good one-way deal

$86 or less
From Chicago Midway to Toronto (YTO)
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One-way flight from Chicago Midway to Toronto (YTO)
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Highest demand for flights based on searches. 5% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 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 Chicago Midway to Toronto (YTO).
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Price to beat on a one-way flight from Chicago Midway to Toronto (YTO).
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Find flight deals from Midway to Toronto

Cheapest flights from Midway to Toronto
Explore the most affordable flight options available from Midway to Toronto. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

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.
Wed 9/39:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 9/67:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/13$191
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.
Wed 9/39:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 9/77:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/13$192
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/189:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 9/207:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/14$193
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 9/93:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/12$195
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/105:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 9/137:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/12$196
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/29:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 10/57:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/14$197
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/145:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 10/197:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/14$198
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/119:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 9/187:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/12$199
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/165:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 9/193:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/14$200
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/59:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 9/77:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/12$201
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/299:35 amMDW - YYZ
1 stop6h 44mDelta
Sat 11/112:15 pmYYZ - MDW
1 stop6h 40mDelta
Deal found 8/13$233
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/271:43 pmMDW - YYZ
1 stop8h 37mDelta
Sat 10/46:00 amYYZ - MDW
1 stop8h 03mDelta
Deal found 8/13$251

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Toronto 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 Chicago Midway Airport to Toronto that are best for you.

Fly from

Midway

Fly to

Toronto

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 10/17

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 10/19

7:50 am-8:39 am

Nonstop1h 49m

$191

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 9/15

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Mon 9/22

3:35 pm-4:24 pm

Nonstop1h 49m

$191

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 9/11

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 9/14

7:50 am-8:39 am

Nonstop1h 49m

$191

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 9/3

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sat 9/6

7:50 am-8:39 am

Nonstop1h 49m

$191

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 9/19

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Mon 9/22

3:35 pm-4:24 pm

Nonstop1h 49m

$191

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 9/12

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 9/14

7:50 am-8:39 am

Nonstop1h 49m

$191

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 9/3

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 9/7

7:50 am-8:39 am

Nonstop1h 49m

$192

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 9/11

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Thu 9/18

7:50 am-8:39 am

Nonstop1h 49m

$193

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 9/19

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sat 9/20

7:50 am-8:39 am

Nonstop1h 49m

$193

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 9/20

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Mon 9/22

3:35 pm-4:24 pm

Nonstop1h 49m

$193

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 36 results
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Best time to book a flight from Midway to Toronto

Have a flexible travel schedule? Discover the best time to fly to Toronto from Midway 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 Chicago Midway Airport to Toronto

What is the cheapest time of day to fly from MDW to YTO?

Find hourly flight availability from Midway to Toronto. 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 Chicago Midway Airport to Toronto, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 24% versus a flight in the evening.

Weekly flight availability from Chicago Midway Airport to Toronto

Explore weekly flight availability from Midway to Toronto. 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 MDW to YTO 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 Toronto

Get insights into the airlines that provide service to Toronto. 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 Toronto. Reviews last updated August 14, 2025.
Read reviews from past customers who have flown Porter Airlines from Chicago Midway Airport to Toronto. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
332 reviews

Food

7.6

Crew

8.7

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Overall

8.0

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

Food

7.6

Crew

8.7

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Overall

8.0

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 Midway to Toronto. 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 Chicago Midway Airport to Toronto round-trip?

    Cheapflights users have booked flights from Chicago Midway Airport to Toronto round-trip from $187. Users have found that Porter Airlines is 34% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Toronto one-way?

    The cheapest airlines for a one-way flight from Chicago Midway Airport to Toronto are Porter Airlines ($74), Delta ($89), and WestJet ($121).

  • Can I find deals for flights from Midway to Toronto that include hotel bookings?

    Yes. In addition to deals on Midway to Toronto flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Toronto?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Toronto.

  • Can I find deals for business class flights from Midway to Toronto?

    Yes. Cheapflights offers flight deals from Midway to Toronto 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 Chicago Midway Airport to Toronto?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto (average of $243). Flying from Chicago Midway Airport to Toronto in August is currently the most expensive (average of $348). 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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Top airline flying from Midway to Toronto

Discover the top airline that operate flights from Midway to Toronto. 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$187Average$271FlexibilityNo cancel feeOn-time52%

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