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Cheap flights from Toronto to Chicago Midway Airport from C$ 186

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 20/6. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
6 Jul — 13 Jul1
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 6 June 2026.

Fri 3/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 6/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 1/6C$ 281
Fri 26/68:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 2/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 2/6C$ 282
Mon 22/68:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 25/610:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 2/6C$ 284
Mon 15/68:45 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 23/610:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 1/6C$ 285
Thu 25/61:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 28/610:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 3/6C$ 287
Fri 26/68:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 28/610:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/6C$ 288
Tue 23/68:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 25/610:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 1/6C$ 289
Wed 24/68:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 26/610:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 3/6C$ 294
Fri 25/94:05 p.m.
YYZ
-
MDW
1 stop3h 28m
Delta
Mon 28/99:30 a.m.
MDW
-
YYZ
1 stop6h 50m
Delta
Deal found 1/6C$ 363
Thu 18/62:29 p.m.
YYZ
-
MDW
1 stop5h 02m
Delta
Sat 20/66:35 p.m.
MDW
-
YYZ
1 stop3h 27m
Delta
Deal found 1/6C$ 366
Tue 1/99:50 a.m.
YYZ
-
MDW
1 stop8h 14m
WestJet
Fri 4/91:32 p.m.
MDW
-
YYZ
1 stop8h 32m
WestJet
Deal found 4/6C$ 370
Tue 23/612:09 p.m.
YYZ
-
MDW
1 stop7h 22m
Delta
Sat 27/69:17 a.m.
MDW
-
YYZ
1 stop5h 02m
Delta
Deal found 2/6C$ 384

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 6 June 2026.

Round-trip from

C$ 281

One-way from

C$ 186

Popular in

March

Cheapest in

September

Average price

C$ 359

Good round-trip deal

C$ 294 or less

Good one-way deal

C$ 205 or less
Porter Airlines
  • Porter Airlines
  • 3/7-6/7
  • Nonstop
  • 3h 30m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 20/6
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (C$ 4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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 629,999 searches. Data last updated 6 June 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
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 17/7

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

Nonstop1h 50m

Chicago Midway

Sun 19/7

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

Nonstop1h 40m

C$ 306

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 1/7

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

Nonstop1h 50m

Chicago Midway

Mon 6/7

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

Nonstop1h 40m

C$ 320

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 24/6

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

Nonstop1h 50m

Chicago Midway

Sun 28/6

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

Nonstop1h 40m

C$ 346

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 7/7

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

Nonstop1h 50m

Chicago Midway

Fri 10/7

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 355

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 18/6

2:29 p.m.-6:31 p.m.

1 stop5h 02m

Chicago Midway

Sun 21/6

9:17 a.m.-5:24 p.m.

1 stop7h 07m

C$ 366

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 27/8

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

Nonstop1h 50m

Chicago Midway

Fri 28/8

10:20 a.m.-1:00 p.m.

Nonstop1h 40m

C$ 366

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 21/8

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

Nonstop1h 50m

Chicago Midway

Sat 22/8

10:20 a.m.-1:00 p.m.

Nonstop1h 40m

C$ 366

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 23/6

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

Nonstop1h 50m

Chicago Midway

Sun 28/6

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 374

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 23/6

12:09 p.m.-6:31 p.m.

1 stop7h 22m

Chicago Midway

Sat 27/6

1:26 p.m.-11:02 p.m.

1 stop8h 36m

C$ 394

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 30/6

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

Nonstop1h 50m

Chicago Midway

Wed 1/7

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 394

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

Showing 1-10 of 45 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$ 111). Flying from Toronto to Chicago Midway Airport in December is currently the most expensive (average of C$ 270). 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 6 June 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 55% 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 6 June 2026.

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

How often are flights from Toronto to Chicago delayed?

About 16% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 113 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?

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 15% 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 6 June 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
440 reviews
Check prices

Crew

8.6

Entertainment

6.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Porter Airlines
8.0
Very good
440 reviews
Porter Airlines
8.0
Very good
440 reviews
Check prices

Crew

8.6

Entertainment

6.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Air Transat
7.8
Good
554 reviews
Porter Airlines
8.0
Very good
440 reviews
Check prices

Crew

8.6

Entertainment

6.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

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 and Delta can get you from Toronto to Chicago Midway Airport in just under 1h 50m. Your travel time can differ by up to 3h 12m. 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$ 114, was found to be the cheapest airline from Toronto to Chicago Midway Airport.. Users have found that Porter Airlines is 65% 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$ 111). Flying from Toronto to Chicago Midway Airport in December is currently the most expensive (average of C$ 270). 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 6 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 114AverageC$ 314FlexibilityNo 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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