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$111+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YTO
Aug 28 — Sep 41
Fri 8/28
Fri 9/4
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 July 29, 2026.

This oojo deal was found by Cheapflights users on 7/28. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:45 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sat 9/51:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/28$236
This oojo deal was found by Cheapflights users on 7/28. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/911:45 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Wed 9/1610:10 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/28$237
This Super.com deal was found by Cheapflights users on 7/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/33:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Tue 9/81:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/28$238
This Trip.com deal was found by Cheapflights users on 7/25. 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 8/2910:20 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sat 9/51:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/25$239
This Justfly.com deal was found by Cheapflights users on 7/28. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:45 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Mon 9/710:10 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/28$241
This FlightHub deal was found by Cheapflights users on 7/26. 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.
Fri 8/2110:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Wed 9/21:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/26$242
This Super.com deal was found by Cheapflights users on 7/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/33:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sun 9/61:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/27$243
This Porter Airlines deal was found by Cheapflights users on 7/27. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sun 9/1310:10 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/27$245
This Super.com deal was found by Cheapflights users on 7/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sun 8/301:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/26$246
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 9/33:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Fri 9/1110:10 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/28$247
This Justfly.com deal was found by Cheapflights users on 7/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/33:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sun 9/1310:10 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/27$248
This Trip.com deal was found by Cheapflights users on 7/26. 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 9/33:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Mon 9/710:10 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/26$249

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 July 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$236
(oojo)

One-way from

$111
(Delta)

Popular in

August

Cheapest in

January

Average price

$271

Good round-trip deal

$242 or less

Good one-way deal

$147 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. 10% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 July 29, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Toronto that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 9/3

3:20 pm-6:00 pm

Nonstop1h 40m

Toronto Island

Sun 9/6

1:45 pm-2:35 pm

Nonstop1h 50m

$239

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 9/9

3:20 pm-6:00 pm

Nonstop1h 40m

Toronto Island

Sun 9/13

10:10 am-11:00 am

Nonstop1h 50m

$245

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 9/9

11:45 am-2:25 pm

Nonstop1h 40m

Toronto Island

Wed 9/16

10:10 am-11:00 am

Nonstop1h 50m

$245

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 8/24

10:25 am-1:05 pm

Nonstop1h 40m

Toronto Island

Mon 8/31

1:45 pm-2:35 pm

Nonstop1h 50m

$255

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 9/8

3:20 pm-6:00 pm

Nonstop1h 40m

Toronto Island

Tue 9/15

10:10 am-11:00 am

Nonstop1h 50m

$271

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 8/21

10:25 am-1:05 pm

Nonstop1h 40m

Toronto Island

Fri 8/28

8:55 am-9:45 am

Nonstop1h 50m

$278

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 9/11

5:03 pm-10:59 pm

1 stop4h 56m

Toronto Pearson Intl

Fri 9/18

12:08 pm-6:33 pm

1 stop7h 25m

$279

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 9/28

9:29 am-3:15 pm

1 stop4h 46m

Toronto Pearson Intl

Wed 9/30

4:05 pm-6:33 pm

1 stop3h 28m

$279

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 9/8

9:29 am-5:20 pm

1 stop6h 51m

Toronto Pearson Intl

Tue 9/15

12:08 pm-6:33 pm

1 stop7h 25m

$279

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 9/3

1:25 pm-11:03 pm

1 stop8h 38m

Toronto Pearson Intl

Tue 9/8

12:08 pm-4:57 pm

1 stop5h 49m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 35 resultsSorted by cheapest first
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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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy1 starTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Toronto flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto (average of $205). Flying from Chicago Midway Airport to Toronto in February is currently the most expensive (average of $656). 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 July 29, 2026.

When flying from Chicago Midway Airport to Toronto, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

How much does it cost to fly round-trip from Chicago Midway Airport to Toronto?

Airfare is below average for this route at the moment.
Chicago Midway Airport to Toronto flights typically cost between $280 and $362 in September.
The cheapest round-trip price found within the last 5 days was $236 on Porter Airlines (Sep 2-Sep 5).

How often are flights from Chicago to Toronto delayed?

About 15% of weekly flights between Chicago and Toronto have experienced delays in the past year, with the average delay time being 114 minutes.

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

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

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

Saturday 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 15% 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 July 29, 2026.
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
449 reviews

Boarding

8.2

Entertainment

6.9

Food

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Porter Airlines
8.0
Very good
449 reviews
Porter Airlines
8.0
Very good
449 reviews

Boarding

8.2

Entertainment

6.9

Food

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

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 40m. Porter Airlines provides one of the quickest options available for as low as $239. 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 are the cheapest airlines flying from Chicago Midway Airport to Toronto round-trip?

    Cheapflights users have booked flights from Chicago Midway Airport to Toronto round-trip from $88. Another airline that can offer you cheap pricing is Porter Airlines. Users have found that Delta is 65% 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto (average of $205). Flying from Chicago Midway Airport to Toronto in February is currently the most expensive (average of $656). 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 2 airlines flying from Midway to Toronto

Discover the top 2 airlines 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 July 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$88Average$359FlexibilityNo cancel feeOn-timeN/A
Porter AirlinesCheapest$174Average$292FlexibilityNo cancel feeOn-time52%

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