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$136+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$234
(Kiwi.com)

One-way from

$136
(SmartFares)

Popular in

January

Cheapest in

September

Average price

$174

Good round-trip deal

$181 or less

Good one-way deal

$179 or less
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 ($24 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 September 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 September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Tue 10/147:30 pmYTZ - MDW
1 stop4h 55mMultiple Airlines
Wed 10/229:35 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 9/15$234
This Bravofly deal was found by Cheapflights users on 9/14. 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 Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:20 amYYZ - MDW
1 stop5h 10mWestJet
Sat 10/2510:35 amMDW - YYZ
1 stop5h 15mWestJet
Deal found 9/14$236
This SmartFares deal was found by Cheapflights users on 9/14. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/187:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Sat 10/259:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/14$240
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/163:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 10/199:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/15$241
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/147:30 pmYTZ - MDW
1 stop4h 55mMultiple Airlines
Sat 10/189:35 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 9/13$242
This SmartFares deal was found by Cheapflights users on 9/14. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/187:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 10/209:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/14$243
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/289:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 11/44:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/13$244
This SmartFares deal was found by Cheapflights users on 9/13. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/177:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 10/209:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/13$245
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Tue 10/147:30 pmYTZ - MDW
1 stop4h 55mMultiple Airlines
Tue 10/219:35 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 9/15$246
This Trip.com deal was found by Cheapflights users on 9/14. 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.
Mon 10/67:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Thu 10/99:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/14$247
This SmartFares deal was found by Cheapflights users on 9/14. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/173:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Tue 10/219:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/14$248
This FlightHub deal was found by Cheapflights users on 9/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/153:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 10/205:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/13$249

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 September 15, 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

Tue 10/14

7:30 pm-11:25 pm

1 stop4h 55m

Chicago Midway

Wed 10/22

9:35 am-12:17 pm

Nonstop1h 42m

$234

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 10/14

7:30 pm-11:25 pm

1 stop4h 55m

Chicago Midway

Thu 10/23

9:35 am-12:17 pm

Nonstop1h 42m

$234

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 10/12

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Mon 10/20

9:35 am-12:17 pm

Nonstop1h 42m

$240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 10/13

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Tue 10/21

9:35 am-12:17 pm

Nonstop1h 42m

$240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 10/18

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Sat 10/25

9:35 am-12:17 pm

Nonstop1h 42m

$240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 10/16

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Tue 10/21

9:35 am-12:17 pm

Nonstop1h 42m

$240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 10/12

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Thu 10/23

9:35 am-12:17 pm

Nonstop1h 42m

$240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 10/14

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Wed 10/22

9:35 am-12:17 pm

Nonstop1h 42m

$240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 10/14

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Mon 10/20

9:35 am-12:17 pm

Nonstop1h 42m

$240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 10/28

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Tue 11/4

4:15 pm-6:57 pm

Nonstop1h 42m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 43 results
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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, April is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of $160). Flying from Toronto to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 15, 2025.

It’s optimal to fly from Toronto to Chicago Midway Airport at noon. By choosing this option you can save up to 56% on the cost of your flight, compared to a flight in the morning.

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 September 15, 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).

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 September 15, 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
7.9
Good
363 reviews

Entertainment

7.0

Overall

7.9

Comfort

7.9

Boarding

8.1

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
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Overall

7.9

Comfort

7.9

Boarding

8.1

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 49m. 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 34% 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, April is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of $160). Flying from Toronto to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Benton Harbor
Porter
Chesterton

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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$258FlexibilityNo cancel feeOn-time52%

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