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$81+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YTO
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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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 September 17, 2025.

Round-trip from

$230
(Kiwi.com)

One-way from

$81
(Kiwi.com)

Popular in

March

Cheapest in

July

Average price

$246

Good round-trip deal

$196 or less

Good one-way deal

$88 or less
From Chicago Midway to Toronto (YTO)
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One-way flight from Chicago Midway to Toronto (YTO)
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Highest demand for flights based on searches. 5% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 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 Chicago Midway to Toronto (YTO).
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Price to beat on a one-way flight from Chicago Midway to Toronto (YTO).
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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 September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/159:35 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Wed 10/2212:00 pmYTZ - MDW
2 stops22h 47mMultiple Airlines
Deal found 9/17$230
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/319:32 amMDW - YYZ
1 stop9h 28mMultiple Airlines
Fri 11/712:50 pmYYZ - MDW
1 stop10h 30mMultiple Airlines
Deal found 9/16$241
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.
Sat 10/189:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 10/207:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/15$244
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Mon 10/209:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 10/247:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/17$248
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.
Mon 10/69:35 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Tue 10/77:30 pmYTZ - MDW
1 stop4h 55mMultiple Airlines
Deal found 9/15$249
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.
Wed 10/159:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 10/163:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/15$250
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.
Sat 10/189:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 10/193:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/15$252
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.
Wed 10/159:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 10/153:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/15$254
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 10/79:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 10/87:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/15$255
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.
Mon 10/69:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 10/73:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/15$256
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.
Sat 10/119:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 10/137:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/15$257
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Tue 10/79:35 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Tue 10/75:15 pmYTZ - MDW
1 stop7h 10mMultiple Airlines
Deal found 9/16$259

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 September 17, 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

Thu 10/23

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Thu 10/30

3:00 pm-11:25 pm

1 stop9h 25m

$246

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 10/15

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Wed 10/22

3:35 pm-4:24 pm

Nonstop1h 49m

$250

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 10/15

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Thu 10/16

3:35 pm-4:24 pm

Nonstop1h 49m

$250

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 10/4

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Tue 10/7

7:30 pm-11:25 pm

1 stop4h 55m

$259

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 10/4

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Tue 10/7

7:50 am-8:39 am

Nonstop1h 49m

$262

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 10/6

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Tue 10/7

7:30 pm-1:38 pm

2 stops19h 08m

$272

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 10/9

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 10/12

7:50 am-8:39 am

Nonstop1h 49m

$273

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 10/11

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 10/12

7:50 am-8:39 am

Nonstop1h 49m

$276

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 11/20

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 11/23

9:15 am-10:05 am

Nonstop1h 50m

$276

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 10/14

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Fri 10/17

3:35 pm-4:24 pm

Nonstop1h 49m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 44 results
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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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto (average of $243). Flying from Chicago Midway Airport to Toronto in August is currently the most expensive (average of $348). 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 September 17, 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 afternoon, which can drop the price by up to 25% versus a flight in the evening.

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 September 17, 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 September 17, 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
7.9
Good
365 reviews

Comfort

7.9

Boarding

8.2

Food

7.6

Crew

8.6

Entertainment

7.0

Overall

7.9

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
365 reviews
Porter Airlines
7.9
Good
365 reviews

Comfort

7.9

Boarding

8.2

Food

7.6

Crew

8.6

Entertainment

7.0

Overall

7.9

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 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 $250. 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 $187. Users have found that Porter Airlines is 33% 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto (average of $243). Flying from Chicago Midway Airport to Toronto in August is currently the most expensive (average of $348). 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 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$187Average$257FlexibilityNo cancel feeOn-time52%

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