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Cheap flights from Canada to Chicago Midway Airport from C$ 160

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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
25 Apr — 2 May1
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
Explore the most affordable flight options available from Canada to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 26 March 2026.

Thu 30/46:50 a.m.
YUL
-
MDW
1 stop4h 25m
Porter Airlines
Sun 3/510:30 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 23/3C$ 241
Fri 8/56:30 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Mon 11/53:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 25/3C$ 247
Fri 8/56:30 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Sun 10/510:30 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 25/3C$ 248
Thu 30/46:50 a.m.
YUL
-
MDW
1 stop4h 25m
Porter Airlines
Tue 12/510:30 a.m.
MDW
-
YUL
1 stop6h 45m
Porter Airlines
Deal found 25/3C$ 250
Wed 6/56:30 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Wed 13/53:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 22/3C$ 251
Thu 7/56:30 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Sun 10/510:30 a.m.
MDW
-
YUL
1 stop6h 45m
Porter Airlines
Deal found 22/3C$ 252
Fri 1/56:30 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Mon 4/53:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 23/3C$ 259
Thu 30/46:50 a.m.
YUL
-
MDW
1 stop4h 25m
Porter Airlines
Mon 11/510:30 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 25/3C$ 263
Mon 25/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 19/63:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 21/3C$ 266
Sat 2/58:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 4/510:30 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/3C$ 270
Mon 4/58:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Thu 7/510:30 a.m.
MDW
-
YTZ
Nonstop1h 40m
Multiple Airlines
Deal found 25/3C$ 273
Thu 4/66:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Sun 7/610:25 a.m.
MDW
-
YUL
1 stop6h 50m
Porter Airlines
Deal found 25/3C$ 273

Find flight deals from Canada to Midway

Keep the following information in mind while searching for Canada to Midway flight deals. Data was last updated 26 March 2026.

Round-trip from

C$ 241

One-way from

C$ 160

Popular in

December

Cheapest in

July

Average price

C$ 372

Good round-trip deal

C$ 300 or less
Porter Airlines
  • Porter Airlines
  • 30/4-3/5
  • 2 total stops
  • 10h 10m total
  • Canada to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 8/5
  • 1 total stop
  • 4h 10m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 6 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 Canada to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Canada 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 26 March 2026.
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

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 11/4

11:20 a.m.-12:10 p.m.

Nonstop1h 50m

Chicago Midway

Sat 18/4

12:55 p.m.-3:37 p.m.

Nonstop1h 42m

C$ 280
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 13/5

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

Nonstop1h 50m

Chicago Midway

Wed 20/5

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

Nonstop1h 40m

C$ 285

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 10/5

6:10 a.m.-12:42 p.m.

1 stop7h 32m

Chicago Midway

Sun 17/5

9:22 a.m.-5:21 p.m.

1 stop6h 59m

C$ 308

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 2/5

6:10 a.m.-8:47 a.m.

1 stop3h 37m

Chicago Midway

Mon 4/5

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

1 stop3h 18m

C$ 309

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 23/6

6:10 a.m.-9:14 a.m.

1 stop4h 04m

Chicago Midway

Sat 27/6

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

1 stop7h 07m

C$ 309

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 19/6

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

1 stop7h 22m

Chicago Midway

Mon 29/6

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

1 stop7h 07m

C$ 309

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 28/4

6:00 a.m.-12:43 p.m.

1 stop7h 43m

Chicago Midway

Tue 12/5

5:10 p.m.-11:57 p.m.

1 stop5h 47m

C$ 321

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 21/4

12:42 p.m.-10:28 p.m.

1 stop10h 46m

Chicago Midway

Thu 23/4

12:52 p.m.-11:51 p.m.

1 stop9h 59m

C$ 321

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 28/4

12:55 p.m.-5:58 p.m.

1 stop6h 03m

Chicago Midway

Fri 15/5

12:53 p.m.-11:57 p.m.

1 stop10h 04m

C$ 321

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 25/4

12:42 p.m.-10:28 p.m.

1 stop10h 46m

Chicago Midway

Tue 28/4

1:24 p.m.-11:08 p.m.

1 stop8h 44m

C$ 323

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/3

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
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 Canada to Chicago Midway Airport

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

Currently, June is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 114). Flying from Canada to Chicago Midway Airport in December is currently the most expensive (average of C$ 285). 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?

Find hourly flight availability from Canada 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 26 March 2026.

It’s optimal to fly from Canada to Chicago Midway Airport in the morning. By choosing this option you can save up to 57% on the cost of your flight, compared to a flight in the evening.

How often are flights from Canada to Chicago delayed?

About 15% of weekly flights between Canada 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 Canada 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 Canada 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 26 March 2026.
Check out reviews from past customers who have flown with Porter Airlines and Air Transat 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
428 reviews
Check prices

Crew

8.6

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

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
428 reviews
Porter Airlines
8.0
Very good
428 reviews
Check prices

Crew

8.6

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

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
525 reviews
Porter Airlines
8.0
Very good
428 reviews
Check prices

Crew

8.6

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

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 Canada 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 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, June is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 114). Flying from Canada to Chicago Midway Airport in December is currently the most expensive (average of C$ 285). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top airline flying from Canada to Midway

Discover the top airline that operate flights from Canada 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 26 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 113AverageC$ 383FlexibilityNo 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 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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