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$130+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Cheap 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 November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$184
(FlightHub)

One-way from

$130
(Mytrip)

Popular in

January

Cheapest in

September

Average price

$251

Good round-trip deal

$333 or less

Good one-way deal

$189 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago Midway flights.
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From Toronto (YTO) to Chicago Midway
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One-way flight from Toronto (YTO) to Chicago Midway
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Highest demand for flights based on searches. 8% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Toronto (YTO) to Chicago Midway.
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Price to beat on a one-way flight from Toronto (YTO) to Chicago Midway.
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Find 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 November 2, 2025.

This FlightHub deal was found by Cheapflights users on 11/1. 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 11/212:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 11/2311:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/1$184
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/42:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 12/124:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/2$187
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/122:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 12/144:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/1$190
This Trip.com deal was found by Cheapflights users on 10/31. 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 11/199:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 11/2111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/31$193
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/99:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 12/124:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/31$194
This SmartFares deal was found by Cheapflights users on 10/31. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/149:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 12/612:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/31$195
This SmartFares deal was found by Cheapflights users on 11/2. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/169:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 11/244:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/2$196
This SmartFares deal was found by Cheapflights users on 10/31. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/142:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 11/1611:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/31$197
This Trip.com deal was found by Cheapflights users on 11/1. 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 11/1511:00 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 11/2212:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/1$198
This Trip.com deal was found by Cheapflights users on 10/30. 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 11/239:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 11/284:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$200
This Delta deal was found by Cheapflights users on 11/2. 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 12/212:13 pmYYZ - MDW
1 stop6h 47mDelta
Sat 12/136:46 pmMDW - YYZ
1 stop3h 25mDelta
Deal found 11/2$210
This Delta deal was found by Cheapflights users on 10/31. 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.
Sat 11/2210:05 amYYZ - MDW
1 stop3h 41mDelta
Wed 11/269:34 amMDW - YYZ
1 stop6h 41mDelta
Deal found 10/31$211

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 November 2, 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

Fri 12/12

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Sun 12/14

4:15 pm-6:57 pm

Nonstop1h 42m

$190

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/11

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Sun 12/14

11:00 am-1:42 pm

Nonstop1h 42m

$193

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 12/9

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Fri 12/12

4:15 pm-6:57 pm

Nonstop1h 42m

$194

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 11/15

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Tue 11/18

11:00 am-1:42 pm

Nonstop1h 42m

$198

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 11/15

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Sat 11/22

12:45 pm-3:27 pm

Nonstop1h 42m

$198

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 11/16

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Wed 11/19

11:00 am-1:42 pm

Nonstop1h 42m

$198

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 11/17

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Thu 11/20

4:15 pm-6:57 pm

Nonstop1h 42m

$201

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/20

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Thu 11/27

4:15 pm-6:57 pm

Nonstop1h 42m

$208

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 11/19

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Tue 11/25

11:00 am-1:42 pm

Nonstop1h 42m

$208

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/21

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Tue 11/25

11:00 am-1:42 pm

Nonstop1h 42m

$208

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 41 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 November.
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 December is currently the most expensive (average of $219). 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 November 2, 2025.

It’s optimal to fly from Toronto to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight in the evening.

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

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 November 2, 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
384 reviews

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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 $158 on this airline. Porter Airlines is 35% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Toronto to Chicago Midway Airport one-way?

    $131 is the cheapest one-way deal found within the past few days, from Porter Airlines. You may also be able to find cheap deals on Air Transat and Delta, with prices starting from $133 and $133, respectively.

  • 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 December is currently the most expensive (average of $219). 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
Merrillville
Lansing
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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$231FlexibilityNo cancel feeOn-time52%

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