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Cheap flights from Toronto to Chicago Midway Airport from C$ 274

YTO — MDW
17 Nov — 24 Nov1
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

Mon 9/1112:15 p.m. -
1 stop6h 49m
Tue 1/126:41 p.m. -
1 stop3h 26m
Deal found 14/10C$ 465
Sat 7/119:40 a.m. -
1 stop4h 07m
Sun 8/119:29 a.m. -
1 stop3h 07m
Deal found 17/10C$ 466
Fri 20/116:00 a.m. -
1 stop4h 46m
Tue 24/119:30 a.m. -
1 stop6h 50m
Deal found 14/10C$ 469
Fri 13/116:00 a.m. -
1 stop7h 51m
Sun 15/119:30 a.m. -
1 stop6h 50m
Deal found 14/10C$ 506
Sat 28/116:00 a.m. -
1 stop4h 46m
Thu 3/129:37 a.m. -
1 stop6h 43m
Deal found 17/10C$ 507
Fri 20/1112:15 p.m. -
1 stop6h 49m
Fri 27/1112:05 p.m. -
1 stop4h 15m
Deal found 17/10C$ 509
Thu 5/1112:10 p.m. -
1 stop6h 50m
Sun 8/111:27 p.m. -
1 stop8h 29m
Deal found 14/10C$ 510
Fri 6/116:05 a.m. -
1 stop7h 47m
Sun 8/119:34 a.m. -
1 stop6h 50m
Deal found 16/10C$ 517
Sat 7/119:45 a.m. -
1 stop4h 07m
Sun 8/119:34 a.m. -
1 stop3h 07m
Deal found 17/10C$ 519
Wed 18/119:10 a.m. -
2 stops15h 37m
Sun 22/111:16 p.m. -
2 stops22h 34m
Deal found 14/10C$ 697
Tue 1/127:10 p.m. -
2 stops17h 23m
Sat 5/1212:28 p.m. -
2 stops20h 11m
Deal found 16/10C$ 698
Tue 1/127:10 p.m. -
2 stops17h 23m
Tue 8/1212:28 p.m. -
2 stops20h 11m
Deal found 17/10C$ 701

Find flight deals from Toronto to Midway

Round-trip from

C$ 465

One-way from

C$ 274

Popular in

October

Cheapest in

September

Average price

C$ 666

Good round-trip deal

C$ 344 or less

Good one-way deal

C$ 188 or less
Delta
  • Delta
  • 9/11-1/12
  • 2 total stops
  • 10h 15m total
  • Toronto to Chicago
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Delta
  • Delta
  • 18/11-31/12
  • 1 total stop
  • 7h 51m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 29 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease (C$ 36 potential savings vs. average RT price).
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Average for round-trip flights in October 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

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 30/11

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 276

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 28/11

6:00 a.m.-9:46 a.m.

1 stop4h 46m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 276

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 25/11

6:00 a.m.-9:46 a.m.

1 stop4h 46m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 276

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 8/12

6:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 276

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 17/11

2:20 p.m.-6:04 p.m.

1 stop4h 44m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 277

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 11/11

2:20 p.m.-6:04 p.m.

1 stop4h 44m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 277

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 5/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 277

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 21/11

9:45 a.m.-12:51 p.m.

1 stop4h 06m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 277

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 2/12

2:25 p.m.-6:01 p.m.

1 stop4h 36m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 277

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 15/11

12:15 p.m.-6:04 p.m.

1 stop6h 49m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 277

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/10

Showing 1-10 of 42 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$ 288). Flying from Toronto to Chicago Midway Airport in October is currently the most expensive (average of C$ 734). 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 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 107 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?

Wednesday 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 16% 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
468 reviews
Check prices

Boarding

8.2

Food

7.6

Crew

8.6

Entertainment

7.0

Comfort

8.0

Overall

8.0

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
468 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Boarding

8.2

Food

7.6

Crew

8.6

Entertainment

7.0

Comfort

8.0

Overall

8.0

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?

    Delta and Porter Airlines can get you from Toronto to Chicago Midway Airport in just under 1h 50m. Your travel time can differ by up to 6h 01m. 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$ 252, was found to be the cheapest airline from Toronto to Chicago Midway Airport.. Users have found that Porter Airlines is 36% 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$ 288). Flying from Toronto to Chicago Midway Airport in October is currently the most expensive (average of C$ 734). 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$ 252AverageC$ 344FlexibilityNo 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.

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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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