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$84+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YTO
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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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 November 2, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/31. 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 11/1911:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 11/209:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/31$187
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 11/1911:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 11/239:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/31$188
This Trip.com deal was found by Cheapflights users on 11/1. 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.
Sat 11/1512:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 11/169:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/1$191
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Sun 11/1611:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 11/212:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/1$192
This Trip.com deal was found by Cheapflights users on 10/31. 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 11/1411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 11/179:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/31$193
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Sat 11/1512:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 11/179:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/1$195
This Trip.com deal was found by Cheapflights users on 11/1. 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.
Sat 11/2212:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 11/249:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/1$196
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Sat 11/1512:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 11/189:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/31$197
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 11/1411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 11/189:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/31$198
This Kissandfly.com deal was found by Cheapflights users on 10/31. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 11/169:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/31$199
This Trip.com deal was found by Cheapflights users on 10/30. 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 11/1311:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 11/169:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/30$200
This Trip.com deal was found by Cheapflights users on 10/31. 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 11/2111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 11/239:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/31$205

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 November 2, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$187
(Kiwi.com)

One-way from

$84
(SmartFares)

Popular in

March

Cheapest in

July

Average price

$287

Good round-trip deal

$257 or less

Good one-way deal

$186 or less
Provider with most accurate pricing for Chicago Midway-Toronto (YTO) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Toronto (YTO) flights.
Search Deals
From Chicago Midway to Toronto (YTO)
Search Deals
One-way flight from Chicago Midway to Toronto (YTO)
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Toronto (YTO).
Search Deals
Price to beat on a one-way flight from Chicago Midway to Toronto (YTO).
Search Deals

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 November 2, 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

Wed 11/19

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Thu 11/20

9:15 am-10:05 am

Nonstop1h 50m

$187

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 11/15

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Sun 11/16

9:15 am-10:05 am

Nonstop1h 50m

$191

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 12/12

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Sun 12/14

9:15 am-10:05 am

Nonstop1h 50m

$192

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 11/16

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Fri 11/21

2:30 pm-3:20 pm

Nonstop1h 50m

$192

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 11/16

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 12/7

9:15 am-10:05 am

Nonstop1h 50m

$192

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 11/13

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 11/16

9:15 am-10:05 am

Nonstop1h 50m

$200

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 3/10

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Wed 3/11

9:15 am-10:05 am

Nonstop1h 50m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 1/15

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Tue 1/20

9:15 am-10:05 am

Nonstop1h 50m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 1/15

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Fri 1/16

9:15 am-10:05 am

Nonstop1h 50m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 2/20

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Wed 2/25

9:15 am-10:05 am

Nonstop1h 50m

$204

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 42 results
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Compare providers for flights from Midway to Toronto

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Toronto in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Toronto flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Chicago Midway Airport-Toronto flight deals on Cheapflights vs. Mytrip >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Toronto flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Toronto flights, Cheapflights users trust Mytrip the most. Mytrip has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Toronto flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 month to book a flight from Chicago Midway Airport to Toronto?

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto (average of $135). Flying from Chicago Midway Airport to Toronto in March is currently the most expensive (average of $473). 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 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 November 2, 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 evening, which can drop the price by up to 21% versus a flight in the afternoon.

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 November 2, 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
384 reviews

Boarding

8.2

Entertainment

7.0

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

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
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews

Boarding

8.2

Entertainment

7.0

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

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 Midway to Toronto. 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 Chicago Midway Airport to Toronto?

    A quick flight from Chicago Midway Airport to Toronto can take about 1h 42m. Porter Airlines provides one of the quickest options available for as low as $187. There are 442 mi between Chicago Midway Airport and Toronto. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $185. Users have found that Porter Airlines is 34% cheaper than the other options available to this destination.

  • 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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto (average of $135). Flying from Chicago Midway Airport to Toronto in March is currently the most expensive (average of $473). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$185Average$234FlexibilityNo cancel feeOn-time52%

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