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$94+ 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 16 — Dec 231
Tue 12/16
Tue 12/23
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 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Thu 12/1111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 12/149:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/13$190
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 12/79:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/15$192
This Kiwi.com deal was found by Cheapflights users on 11/14. 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.
Sat 12/612:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 12/79:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/14$199
This Mytrip deal was found by Cheapflights users on 11/16. 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 Mytrip 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
Wed 1/79:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/16$206
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 12/3011:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 1/59:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/13$207
This Flightnetwork deal was found by Cheapflights users on 11/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/294:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 1/59:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/14$209
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 12/3111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 1/69:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/13$210
This Trip.com deal was found by Cheapflights users on 11/13. 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.
Tue 12/211:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 12/52:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/13$211
This Kiwi.com deal was found by Cheapflights users on 11/14. 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.
Sat 12/612:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 12/112:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/14$213
This Trip.com deal was found by Cheapflights users on 11/14. 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.
Fri 12/54:15 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Sun 12/79:15 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 11/14$215
This Delta deal was found by Cheapflights users on 11/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/129:34 amMDW - YYZ
1 stop6h 41mDelta
Sun 12/146:30 amYYZ - MDW
1 stop7h 40mDelta
Deal found 11/15$233
This Delta deal was found by Cheapflights users on 11/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:40 pmMDW - YYZ
1 stop3h 31mDelta
Tue 12/96:05 amYYZ - MDW
1 stop7h 29mDelta
Deal found 11/14$250

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 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$189
(Kiwi.com)

One-way from

$94
(Kiwi.com)

Popular in

March

Cheapest in

July

Average price

$287

Good round-trip deal

$287 or less

Good one-way deal

$210 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. 6% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 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 16, 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 12/5

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Sun 12/7

9:15 am-10:05 am

Nonstop1h 50m

$197

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 12/31

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Wed 1/7

9:15 am-10:05 am

Nonstop1h 50m

$206

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 12/30

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Mon 1/5

9:15 am-10:05 am

Nonstop1h 50m

$207

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 12/31

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Mon 1/5

9:15 am-10:05 am

Nonstop1h 50m

$207

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 12/29

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Mon 1/5

9:15 am-10:05 am

Nonstop1h 50m

$209

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 12/31

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Tue 1/6

9:15 am-10:05 am

Nonstop1h 50m

$210

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 1/1

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Sun 1/11

9:15 am-10:05 am

Nonstop1h 50m

$211

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 1/7

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 1/11

9:15 am-10:05 am

Nonstop1h 50m

$214

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 1/1

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Tue 1/6

9:15 am-10:05 am

Nonstop1h 50m

$216

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 1/2

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Tue 1/6

9:15 am-10:05 am

Nonstop1h 50m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

Showing 1-10 of 44 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
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 November 16, 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 November 16, 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).

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 16, 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
392 reviews

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
392 reviews
Porter Airlines
8.0
Very good
392 reviews

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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 $185. Users have found that Porter Airlines is 32% 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 ($96), Delta ($106), and Air Transat ($110).

  • 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

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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 November 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$185Average$234FlexibilityNo cancel feeOn-time52%

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