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Cheap flights from Canada to Chicago Midway Airport from C$ 194

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 17/7. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
23 Jul — 30 Jul1
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 23 June 2026.

Fri 10/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 13/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 288
Thu 9/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 13/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 289
Mon 6/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 9/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 290
Mon 6/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 8/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/6C$ 292
Sat 4/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/6C$ 293
Sun 5/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 8/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 21/6C$ 295
Wed 8/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 11/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/6C$ 296
Fri 3/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/6C$ 298
Fri 3/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Tue 7/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Air Transat
Deal found 20/6C$ 303
Sat 5/912:09 p.m.
YYZ
-
MDW
1 stop5h 50m
Delta
Tue 8/95:45 p.m.
MDW
-
YYZ
1 stop4h 14m
Delta
Deal found 22/6C$ 336
Wed 30/94:05 p.m.
YYZ
-
MDW
1 stop3h 28m
Delta
Tue 6/109:30 a.m.
MDW
-
YYZ
1 stop3h 02m
Delta
Deal found 22/6C$ 337
Thu 24/92:24 p.m.
YYZ
-
MDW
1 stop5h 09m
Delta
Tue 29/99:30 a.m.
MDW
-
YYZ
1 stop4h 45m
Delta
Deal found 18/6C$ 339

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 23 June 2026.

Round-trip from

C$ 288

One-way from

C$ 194

Popular in

May

Cheapest in

September

Average price

C$ 401

Good round-trip deal

C$ 296 or less

Good one-way deal

C$ 176 or less
Porter Airlines
  • Porter Airlines
  • 10/7-17/7
  • Nonstop
  • 3h 30m total
  • Canada to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 17/7
  • Nonstop
  • 1h 50m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease (C$ 4 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 Canada to Chicago Midway.
Search Deals
Price to beat on a one-way 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 23 June 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
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 18/7

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

Nonstop1h 50m

Chicago Midway

Sun 19/7

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

Nonstop1h 40m

C$ 288

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 16/7

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

Nonstop1h 50m

Chicago Midway

Sat 18/7

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

Nonstop1h 40m

C$ 299

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 20/8

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

Nonstop1h 50m

Chicago Midway

Mon 24/8

3:15 p.m.-5:55 p.m.

Nonstop1h 40m

C$ 299

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 12/7

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

Nonstop1h 50m

Chicago Midway

Tue 14/7

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

Nonstop1h 40m

C$ 302

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 29/7

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

Nonstop1h 50m

Chicago Midway

Thu 6/8

3:15 p.m.-5:55 p.m.

Nonstop1h 40m

C$ 306

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 29/7

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

Nonstop1h 50m

Chicago Midway

Sun 2/8

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

Nonstop1h 40m

C$ 306

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 18/7

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

Nonstop1h 50m

Chicago Midway

Sat 25/7

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

Nonstop1h 40m

C$ 309

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 26/7

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

Nonstop1h 50m

Chicago Midway

Tue 28/7

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

Nonstop1h 40m

C$ 313

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 6/7

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

Nonstop1h 50m

Chicago Midway

Thu 9/7

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

Nonstop1h 40m

C$ 315

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 21/7

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

Nonstop1h 50m

Chicago Midway

Sat 25/7

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

Nonstop1h 40m

C$ 323

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/6

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, August is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 116). Flying from Canada to Chicago Midway Airport in December is currently the most expensive (average of C$ 275). 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 23 June 2026.

It’s optimal to fly from Canada to Chicago Midway Airport in the morning. By choosing this option you can save up to 53% 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 113 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

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 23 June 2026.
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
439 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.5

Crew

8.6

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
439 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.5

Crew

8.6

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 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, August is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 116). Flying from Canada to Chicago Midway Airport in December is currently the most expensive (average of C$ 275). 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 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 23 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 116AverageC$ 347FlexibilityNo 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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