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Cheap flights from Toronto to Chicago Midway Airport from C$ 170

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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
15 Apr — 22 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Toronto to Midway

Enter your travel dates to find the best prices.

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 16 March 2026.

Wed 8/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 12/44:05 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 15/3C$ 278
Thu 23/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 30/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 13/3C$ 280
Tue 5/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 8/53:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 11/3C$ 281
Tue 7/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 11/412:55 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 13/3C$ 284
Thu 23/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 27/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 12/3C$ 285
Sat 25/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 2/510:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 11/3C$ 287
Sun 5/42:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 13/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 11/3C$ 289
Mon 13/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 14/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 12/3C$ 291
Sat 4/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 11/3C$ 292
Thu 30/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 7/53:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 13/3C$ 294
Fri 17/42:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 20/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 11/3C$ 296
Thu 23/42:15 p.m.
YYZ
-
MDW
1 stop4h 43m
Delta
Mon 27/46:38 p.m.
MDW
-
YYZ
1 stop3h 18m
Delta
Deal found 11/3C$ 376

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 16 March 2026.

Round-trip from

C$ 277

One-way from

C$ 170

Popular in

March

Cheapest in

September

Average price

C$ 394

Good round-trip deal

C$ 278 or less
Porter Airlines
  • Porter Airlines
  • 10/4-12/4
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 11/4
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip 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 629,999 searches. Data last updated 16 March 2026.
Use the filters below to find and compare flights from Toronto to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 28/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Wed 29/4

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 307
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 7/5

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Mon 11/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 340

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 8/6

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 10/6

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 340

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 5/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Tue 7/4

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 346

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 23/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Mon 27/4

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 346

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 11/4

6:20 a.m.-8:53 a.m.

1 stop3h 33m

Chicago Midway

Sat 25/4

9:27 a.m.-3:20 p.m.

1 stop4h 53m

C$ 376

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 17/4

2:15 p.m.-5:58 p.m.

1 stop4h 43m

Chicago Midway

Tue 21/4

6:38 p.m.-10:56 p.m.

1 stop3h 18m

C$ 376

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 8/5

6:10 a.m.-8:43 a.m.

1 stop3h 33m

Chicago Midway

Sat 9/5

9:22 a.m.-1:30 p.m.

1 stop3h 08m

C$ 376

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 10/4

6:20 a.m.-8:53 a.m.

1 stop3h 33m

Chicago Midway

Fri 17/4

9:27 a.m.-5:21 p.m.

1 stop6h 54m

C$ 376

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 23/4

2:15 p.m.-5:58 p.m.

1 stop4h 43m

Chicago Midway

Mon 27/4

6:38 p.m.-10:56 p.m.

1 stop3h 18m

C$ 376

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 43 resultsSorted by cheapest first
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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, June is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of C$ 114). Flying from Toronto to Chicago Midway Airport in February is currently the most expensive (average of C$ 387). 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 16 March 2026.

When flying from Toronto to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 57% versus 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 16 March 2026.

The most flights from YTO to MDW are scheduled on a Thursday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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

How often are flights from Toronto to Chicago delayed?

About 15% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 110 minutes.

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

Historically, flights departing in the evening 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?

Thursday 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 past year, Porter Airlines has 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 16 March 2026.
Get a feel of what it's like to fly with Porter Airlines and Air Transat from Toronto to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
424 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
424 reviews
Porter Airlines
8.0
Very good
424 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Transat
7.7
Good
521 reviews
Porter Airlines
8.0
Very good
424 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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?

    Porter Airlines, Air Transat, and Delta can get you from Toronto to Chicago Midway Airport in just under 1h 50m. Your travel time can differ by up to 1h 43m. There are 711 km between Toronto and Chicago Midway Airport. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What is the cheapest airline to fly from Toronto to Chicago Midway Airport round-trip?

    Porter Airlines, at C$ 112, was found to be the cheapest airline from Toronto to Chicago Midway Airport.. Users have found that Porter Airlines is 64% cheaper than the other options available 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 C$ 114). Flying from Toronto to Chicago Midway Airport in February is currently the most expensive (average of C$ 387). 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 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 629,999 searches. Data last updated 16 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 112AverageC$ 336FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Toronto to Midway?

When you search for this flight from Toronto to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Toronto to Midway?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Toronto to Midway.

Can Cheapflights find flights from Toronto to Midway with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Toronto to Midway flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Toronto to Midway become cheaper?

Yes, Cheapflights offers price alerts on Toronto to Midway flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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