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$101+ 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 6/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YTO
Jul 14 — Jul 211
Tue 7/14
Tue 7/21
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 June 14, 2026.

This Trip.com deal was found by Cheapflights users on 6/10. 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 6/253:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Mon 6/298:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 6/10$218
This Trip.com deal was found by Cheapflights users on 6/11. 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 7/103:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Mon 7/131:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 6/11$219
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 6/3010:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sat 7/48:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 6/11$220
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Sat 6/2710:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sat 7/48:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 6/13$221
This Trip.com deal was found by Cheapflights users on 6/10. 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 7/23:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sun 7/58:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 6/10$222
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Sat 6/2710:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Tue 6/308:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 6/13$223
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 7/2210:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Mon 7/278:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 6/11$224
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Mon 6/2910:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sat 7/188:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 6/13$226
This Trip.com deal was found by Cheapflights users on 6/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2710:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Mon 6/298:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 6/13$227
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Sat 6/2710:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sun 6/281:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 6/13$228
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Tue 8/2510:20 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sat 8/298:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 6/13$229
This Kissandfly.com deal was found by Cheapflights users on 6/11. 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.
Thu 7/21:26 pm
MDW
-
YYZ
1 stop8h 36m
KLM
Sun 7/56:05 am
YYZ
-
MDW
1 stop7h 41m
KLM
Deal found 6/11$265

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 June 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$218
(Trip.com)

One-way from

$101
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$269

Good round-trip deal

$247 or less

Good one-way deal

$117 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. 13% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 14, 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

Wed 7/1

3:20 pm-6:00 pm

Nonstop1h 40m

Toronto Island

Sat 7/4

8:50 am-9:40 am

Nonstop1h 50m

$225

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 7/4

10:25 am-1:05 pm

Nonstop1h 40m

Toronto Island

Mon 7/6

8:50 am-9:40 am

Nonstop1h 50m

$227

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 7/31

3:20 pm-6:00 pm

Nonstop1h 40m

Toronto Island

Sun 8/2

8:50 am-9:40 am

Nonstop1h 50m

$237

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 9/9

9:29 am-5:20 pm

1 stop6h 51m

Toronto Pearson Intl

Tue 9/15

6:00 am-12:34 pm

1 stop7h 34m

$273

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 7/7

10:25 am-1:05 pm

Nonstop1h 40m

Toronto Island

Thu 7/23

8:50 am-9:40 am

Nonstop1h 50m

$287

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 7/1

10:25 am-1:05 pm

Nonstop1h 40m

Toronto Island

Sun 7/5

8:50 am-9:40 am

Nonstop1h 50m

$287

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 7/2

1:26 pm-11:02 pm

1 stop8h 36m

Toronto Pearson Intl

Mon 7/6

6:05 am-12:46 pm

1 stop7h 41m

$290

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 8/13

9:24 am-5:24 pm

1 stop7h 00m

Toronto Pearson Intl

Sun 8/16

6:10 am-12:39 pm

1 stop7h 29m

$290

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 7/4

5:50 pm-11:02 pm

1 stop4h 12m

Toronto Pearson Intl

Mon 7/6

6:05 am-12:46 pm

1 stop7h 41m

$290

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 7/25

6:35 pm-11:02 pm

1 stop3h 27m

Toronto Pearson Intl

Tue 7/28

6:10 am-9:13 am

1 stop4h 03m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/13

Showing 1-10 of 45 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 June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto (average of $58). Flying from Chicago Midway Airport to Toronto in October is currently the most expensive (average of $199). 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 June 14, 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.

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 June 14, 2026.

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

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 116 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?

Thursday 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 14% 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 June 14, 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
438 reviews

Entertainment

6.9

Overall

8.0

Boarding

8.2

Food

7.6

Crew

8.6

Comfort

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Porter Airlines
8.0
Very good
438 reviews
Porter Airlines
8.0
Very good
438 reviews

Entertainment

6.9

Overall

8.0

Boarding

8.2

Food

7.6

Crew

8.6

Comfort

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

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 $225. 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 62% 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 $58). Flying from Chicago Midway Airport to Toronto in October is currently the most expensive (average of $199). 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 June 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$88Average$303FlexibilityNo cancel feeOn-timeN/A
Porter AirlinesCheapest$174Average$275FlexibilityNo cancel feeOn-time52%

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