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

YYZ — MDW
17 Oct — 24 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Canada to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Canada to Midway

Sun 11/1010:10 a.m. -
Nonstop1h 50m
Wed 14/1011:45 a.m. -
Nonstop1h 40m
Deal found 12/9C$ 289
Wed 7/1010:10 a.m. -
Nonstop1h 50m
Fri 9/103:20 p.m. -
Nonstop1h 40m
Deal found 16/9C$ 293
Sun 11/1010:10 a.m. -
Nonstop1h 50m
Sun 18/103:20 p.m. -
Nonstop1h 40m
Deal found 16/9C$ 298
Sun 11/101:45 p.m. -
Nonstop1h 50m
Sun 18/1011:45 a.m. -
Nonstop1h 40m
Deal found 13/9C$ 321
Fri 20/1112:15 p.m. -
1 stop6h 49m
Tue 24/119:30 a.m. -
1 stop3h 00m
Deal found 12/9C$ 321
Wed 25/116:00 a.m. -
1 stop7h 51m
Sat 28/119:30 a.m. -
1 stop6h 50m
Deal found 13/9C$ 324
Tue 13/1010:10 a.m. -
Nonstop1h 50m
Tue 20/1011:45 a.m. -
Nonstop1h 40m
Deal found 14/9C$ 326
Wed 14/1010:10 a.m. -
Nonstop1h 50m
Fri 16/1011:45 a.m. -
Nonstop1h 40m
Deal found 15/9C$ 328
Thu 1/101:45 p.m. -
Nonstop1h 50m
Sun 4/1011:45 a.m. -
Nonstop1h 40m
Deal found 13/9C$ 331
Sat 31/106:00 a.m. -
1 stop4h 32m
Sat 7/111:27 p.m. -
1 stop8h 29m
Deal found 15/9C$ 331
Sat 26/91:45 p.m. -
Nonstop1h 50m
Sun 27/911:45 a.m. -
Nonstop1h 40m
Deal found 12/9C$ 332
Wed 28/106:00 a.m. -
1 stop7h 47m
Fri 30/109:29 a.m. -
1 stop6h 50m
Deal found 14/9C$ 332

Find flight deals from Canada to Midway

Round-trip from

C$ 289

One-way from

C$ 181

Popular in

October

Cheapest in

February

Average price

C$ 390

Good round-trip deal

C$ 329 or less

Good one-way deal

C$ 288 or less
Porter Airlines
  • Porter Airlines
  • 11/10-14/10
  • Nonstop
  • 3h 30m total
  • Canada to Chicago
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Porter Airlines
  • Porter Airlines
  • 30/9-31/12
  • Nonstop
  • 1h 50m total
  • Canada to Chicago
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Highest demand for flights based on searches. 3% potential increase in price (C$ 16 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease (C$ 5 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 Canada to Chicago Midway.
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Price to beat on a one-way flight from Canada to Chicago Midway.
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Canada 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

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$ 184

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 2/10

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$ 185

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 6/10

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$ 190

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 20/10

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$ 206

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 5/10

2:24 p.m.-6:33 p.m.

1 stop5h 09m

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

Thu 15/10

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$ 206

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 28/10

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

Sat 10/10

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$ 206

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 27/9

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$ 206

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 29/9

6:00 a.m.-12:39 p.m.

1 stop7h 39m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 206

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/9

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Canada to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Canada with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Canada to Chicago Midway Airport

What is the cheapest month to book a flight from Canada to Chicago Midway Airport?

Currently, January is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 284). Flying from Canada to Chicago Midway Airport in June is currently the most expensive (average of C$ 549). 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 CA to MDW?

It’s optimal to fly from Canada to Chicago Midway Airport at noon. By choosing this option you can save up to 50% on the cost of your flight, compared to a flight in the evening.

How often are flights from Canada to Chicago delayed?

About 16% of weekly flights between Canada 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 Canada 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 Canada 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

Check out reviews from past customers who have flown with Porter Airlines from Canada to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
462 reviews
Check prices

Entertainment

6.9

Food

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

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
462 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Entertainment

6.9

Food

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

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 Canada to Chicago Midway Airport?

    Departing from Canada to Chicago Midway Airport will take you 1h 50m. The distance from Canada to Chicago Midway Airport is about 711 km. This flight may include one or multiple stops.

  • What are the most popular routes from Canada to Chicago Midway Airport?

    While some choose either Toronto Island - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago Midway, Toronto Pearson Intl - Chicago Midway is the most popular route from Canada to Chicago Midway Airport.

  • Can I find deals for flights from Canada to Midway that include hotel bookings?

    Yes. In addition to deals on Canada to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Canada to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Canada to Midway.

  • Can I find deals for business class flights from Canada to Midway?

    Yes. Cheapflights offers flight deals from Canada 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 Canada to Chicago Midway Airport?

    Currently, January is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 284). Flying from Canada to Chicago Midway Airport in June is currently the most expensive (average of C$ 549). 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 Canada to Midway

AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 221AverageC$ 397FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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

Cheapflights helps you search for flights from Canada to Midway via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

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

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Canada.

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

Yes, we can. To see specific flights from Canada to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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

Yes! Start tracking prices for Canada to Midway flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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