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Cheap flights from Toronto to Chicago Midway Airport from C$ 181

YTO — MDW
9 Oct — 16 Oct1
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

Fri 25/91:45 p.m. -
Nonstop1h 50m
Fri 2/103:20 p.m. -
Nonstop1h 40m
Deal found 8/9C$ 286
Tue 6/101:45 p.m. -
Nonstop1h 50m
Thu 15/103:20 p.m. -
Nonstop1h 40m
Deal found 8/9C$ 287
Sun 18/101:45 p.m. -
Nonstop1h 50m
Mon 19/103:20 p.m. -
Nonstop1h 40m
Deal found 5/9C$ 288
Wed 30/910:10 a.m. -
Nonstop1h 50m
Fri 2/103:20 p.m. -
Nonstop1h 40m
Deal found 8/9C$ 295
Sat 26/910:10 a.m. -
Nonstop1h 50m
Sat 3/1011:45 a.m. -
Nonstop1h 40m
Deal found 8/9C$ 301
Fri 2/1010:10 a.m. -
Nonstop1h 50m
Sun 4/103:20 p.m. -
Nonstop1h 40m
Deal found 8/9C$ 302
Sat 26/910:10 a.m. -
Nonstop1h 50m
Wed 30/911:45 a.m. -
Nonstop1h 40m
Deal found 8/9C$ 303
Wed 14/1010:10 a.m. -
Nonstop1h 50m
Thu 22/103:20 p.m. -
Nonstop1h 40m
Deal found 8/9C$ 305
Fri 25/91:45 p.m. -
Nonstop1h 50m
Wed 30/911:45 a.m. -
Nonstop1h 40m
Deal found 8/9C$ 306
Thu 1/1010:10 a.m. -
Nonstop1h 50m
Sun 4/103:20 p.m. -
Nonstop1h 40m
Deal found 4/9C$ 308
Sat 17/1010:10 a.m. -
Nonstop1h 50m
Fri 23/103:20 p.m. -
Nonstop1h 40m
Deal found 8/9C$ 309
Mon 28/91:45 p.m. -
Nonstop1h 50m
Tue 29/93:20 p.m. -
Nonstop1h 40m
Deal found 8/9C$ 310

Find flight deals from Toronto to Midway

Round-trip from

C$ 286

One-way from

C$ 181

Popular in

June

Cheapest in

September

Average price

C$ 254

Good round-trip deal

C$ 284 or less

Good one-way deal

C$ 192 or less
Porter Airlines
  • Porter Airlines
  • 25/9-1/10
  • Nonstop
  • 3h 30m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 30/9-31/12
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 111 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease (C$ 31 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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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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Cheapflights Fare Finder

 
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 Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sat 17/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 183

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 1/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 197

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 22/10

6:00 a.m.-9:32 a.m.

1 stop4h 32m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 206

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 14/10

2:26 p.m.-6:00 p.m.

1 stop4h 34m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 210

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 13/10

9:40 a.m.-12:47 p.m.

1 stop4h 07m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 210

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 17/10

6:00 a.m.-12:47 p.m.

1 stop7h 47m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 210

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 3/10

6:00 a.m.-9:07 a.m.

1 stop4h 07m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 210

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 30/9

6:00 a.m.-9:07 a.m.

1 stop4h 07m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 210

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 4/11

12:10 p.m.-6:00 p.m.

1 stop6h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 210

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 22/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 211

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

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

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, January is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of C$ 281). Flying from Toronto to Chicago Midway Airport in June is currently the most expensive (average of C$ 543). 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?

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 at noon, which can drop the price by up to 50% versus a flight in the evening.

Weekly flight availability from Toronto to Chicago Midway Airport

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

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

Airfare is above average for this route at the moment.
Toronto to Chicago Midway Airport flights typically cost between C$ 254 and C$ 283 in September.
The cheapest round-trip price found within the last 5 days was C$ 286 on Porter Airlines (25 Sep-1 Oct).

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 104 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 14% of flights being delayed.

Reviews of airlines servicing Midway

Get a feel of what it's like to fly with Porter Airlines 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
458 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

6.9

Food

7.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
458 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

6.9

Food

7.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

  • How long is the flight from Toronto to Chicago Midway Airport?

    Porter Airlines, Delta, and Air Transat can get you from Toronto to Chicago Midway Airport in just under 1h 50m. Your travel time can differ by up to 5h 49m. 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$ 219, was found to be the cheapest airline from Toronto to Chicago Midway Airport.. Users have found that Porter Airlines is 39% 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, January is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of C$ 281). Flying from Toronto to Chicago Midway Airport in June is currently the most expensive (average of C$ 543). 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

Top airline flying from Toronto to Midway

AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 219AverageC$ 334FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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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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