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$116+ Cheap flights from Toronto (YTO) to Midway (MDW)

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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Toronto to Midway

Cheapest flights from Toronto to Midway
Explore the most affordable flight options available from Toronto to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

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.
Tue 12/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 2/311:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$270
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 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 2/311:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$291
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/292:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 1/611:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/16$347
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 2/211:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$355
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 1/2111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/16$362
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3112:09 pmYYZ - MDW
1 stop6h 17mWestJet
Fri 1/26:08 pmMDW - YYZ
1 stop13h 50mWestJet
Deal found 12/17$365
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 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 1/14:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/16$366
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 12/3112:09 pmYYZ - MDW
1 stop6h 17mWestJet
Mon 1/56:14 pmMDW - YYZ
1 stop3h 27mWestJet
Deal found 12/16$366
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.
Sun 12/289:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 1/1012:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/16$368
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 1/44:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/16$369
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 1/311:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/16$370
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 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 1/211:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/16$374

Find flight deals from Toronto to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Toronto (YTO) to Midway (MDW). 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

$183
(Trip.com)

One-way from

$116
(Trip.com)

Popular in

January

Cheapest in

September

Average price

$321

Good round-trip deal

$210 or less

Good one-way deal

$117 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago Midway flights.
Search Deals
From Toronto (YTO) to Chicago Midway
Search Deals
One-way flight from Toronto (YTO) to Chicago Midway
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 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 Toronto (YTO) to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Toronto (YTO) to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Toronto to Midway 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 Toronto to Chicago Midway Airport that are best for you.

Fly from

Toronto

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 1/25

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Mon 1/26

11:00 am-1:42 pm

Nonstop1h 42m

$186

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 2/9

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Tue 2/10

11:00 am-1:42 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/16

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Fri 1/23

11:05 am-1:47 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 2/20

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Mon 2/23

11:00 am-1:42 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 1/24

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Thu 1/29

11:00 am-1:42 pm

Nonstop1h 42m

$188

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 1/14

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Thu 1/15

11:00 am-1:42 pm

Nonstop1h 42m

$205

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 1/14

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sun 1/18

4:15 pm-6:57 pm

Nonstop1h 42m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/5

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Sun 2/8

9:33 am-4:12 pm

1 stop5h 39m

$213

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 2/9

12:12 pm-5:55 pm

1 stop6h 43m

Chicago Midway

Wed 2/11

9:53 am-3:59 pm

1 stop5h 06m

$213

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 1/14

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Wed 1/21

11:00 am-1:42 pm

Nonstop1h 42m

$218

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 39 results
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Compare providers for flights from Toronto to Midway

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 Toronto to Midway in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 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 Toronto-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Toronto-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Toronto-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto-Chicago Midway Airport 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 Toronto-Chicago Midway Airport 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 Toronto to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Toronto 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 Toronto to Chicago Midway Airport

What is the cheapest month to book a flight from Toronto to Chicago Midway Airport?

Currently, June is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of $83). Flying from Toronto to Chicago Midway Airport in November is currently the most expensive (average of $209). 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 YTO to MDW?

Find hourly flight availability from Toronto to Midway. 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.

It’s optimal to fly from Toronto to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 23% on the cost of your flight, compared to a flight in the evening.

Weekly flight availability from Toronto to Chicago Midway Airport

Explore weekly flight availability from Toronto to Midway. 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 YTO to MDW 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 Toronto to Chicago delayed?

About 14% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 107 minutes.

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

Historically, flights departing in the morning 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?

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 Toronto to Chicago 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 Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated December 18, 2025.
Peruse reviews from past customers who have flown with Porter Airlines from Toronto to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
399 reviews

Crew

8.6

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

Comfort

7.9

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

Crew

8.6

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

Comfort

7.9

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 Toronto to Midway. 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 Toronto to Chicago Midway Airport?

    Departing from Toronto to Chicago Midway Airport will take you 1h 50m. Airlines will cover a distance of 442 mi. 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 Toronto to Chicago Midway Airport round-trip?

    Our cheapest airline available from Toronto to Chicago Midway Airport is Porter Airlines. Our recent data shows that you can find tickets from as low as $80 on this airline. Porter Airlines is 67% cheaper than the average price of flights available within the next 90 days to this destination.

  • Can I find deals for flights from Toronto to Midway that include hotel bookings?

    Yes. In addition to deals on Toronto to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Toronto to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Toronto to Midway.

  • Can I find deals for business class flights from Toronto to Midway?

    Yes. Cheapflights offers flight deals from Toronto to Midway 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 Toronto to Chicago Midway Airport?

    Currently, June is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of $83). Flying from Toronto to Chicago Midway Airport in November is currently the most expensive (average of $209). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Toronto to Midway

Discover the top airline that operate flights from Toronto to Midway. 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$158Average$258FlexibilityNo cancel feeOn-time52%

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