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$82+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YTO
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Booking.com deal was found by Cheapflights users on 12/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 1/69:20 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/16$389
This FlightHub deal was found by Cheapflights users on 12/16. 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.
Tue 12/304:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 1/29:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/16$408
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/316:08 pmMDW - YYZ
1 stop16h 11mWestJet
Mon 1/510:05 amYYZ - MDW
1 stop3h 43mWestJet
Deal found 12/16$416
This Trip.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/3111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 1/59:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/16$422
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/316:08 pmMDW - YYZ
1 stop16h 11mMultiple Airlines
Mon 1/58:30 pmYYZ - MDW
2 stops50h 47mMultiple Airlines
Deal found 12/16$431
This Trip.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 1/52:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/16$433
This FlightHub deal was found by Cheapflights users on 12/15. 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.
Wed 12/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 12/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/15$435
This Trip.com deal was found by Cheapflights users on 12/15. 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 12/254:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 12/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/15$437
This FlightHub deal was found by Cheapflights users on 12/16. 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.
Thu 12/254:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 1/119:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/16$441
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/234:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 12/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/16$445
This Trip.com deal was found by Cheapflights users on 12/17. 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.
Sun 12/284:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 1/12:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/17$446
This FlightHub deal was found by Cheapflights users on 12/16. 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.
Wed 12/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 1/12:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/16$452

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$186
(Trip.com)

One-way from

$82
(Trip.com)

Popular in

June

Cheapest in

July

Average price

$276

Good round-trip deal

$243 or less

Good one-way deal

$126 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
High demand for flights, 1% potential price rise
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 18, 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

Thu 1/22

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Mon 1/26

9:20 am-10:10 am

Nonstop1h 50m

$191

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 1/16

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Sun 1/18

2:30 pm-3:20 pm

Nonstop1h 50m

$197

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 1/16

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Fri 1/23

9:15 am-10:05 am

Nonstop1h 50m

$204

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 1/22

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Sun 1/25

2:30 pm-3:20 pm

Nonstop1h 50m

$205

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 1/30

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sat 1/31

11:00 am-11:50 am

Nonstop1h 50m

$210

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 1/31

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Sat 2/7

11:00 am-11:50 am

Nonstop1h 50m

$215

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 1/26

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Tue 1/27

9:20 am-10:10 am

Nonstop1h 50m

$226

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 1/17

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Sun 1/18

9:15 am-10:05 am

Nonstop1h 50m

$230

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 2/10

1:51 pm-11:13 pm

1 stop8h 22m

Toronto Pearson Intl

Fri 2/13

10:05 am-5:37 pm

1 stop8h 32m

$234

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 2/5

9:53 am-3:59 pm

1 stop5h 06m

Toronto Pearson Intl

Mon 2/9

10:05 am-12:46 pm

1 stop3h 41m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 40 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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Toronto flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto (average of $79). Flying from Chicago Midway Airport to Toronto in January is currently the most expensive (average of $333). 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 December 18, 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.

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 December 18, 2025.

The most flights from MDW to YTO are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

How often are flights from Chicago to Toronto delayed?

About 14% of weekly flights between Chicago and Toronto have experienced delays in the past year, with the average delay time being 118 minutes.

What is the most punctual flight time for Chicago to Toronto flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Toronto flights?

Over the last year, Porter Airlines have had the lowest number of delays on this route, with just 13% of flights being delayed.

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 December 18, 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
399 reviews

Entertainment

7.0

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
399 reviews
Porter Airlines
8.0
Very good
399 reviews

Entertainment

7.0

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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 $191. 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 $172. Users have found that Porter Airlines is 33% 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto (average of $79). Flying from Chicago Midway Airport to Toronto in January is currently the most expensive (average of $333). 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$185Average$233FlexibilityNo cancel feeOn-time52%

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