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Cheap flights from Canada to Chicago Midway Airport from C$ 163

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 20/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
7 Jan — 14 Jan1
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 8 December 2025.

Sat 27/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Mon 23/211:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 6/12C$ 299
Sat 27/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 30/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/12C$ 333
Wed 24/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 28/212:50 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/12C$ 339
Wed 24/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 25/211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/12C$ 340
Sun 28/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Tue 30/1211:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 7/12C$ 353
Mon 29/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/12C$ 366
Tue 30/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 9/111:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/12C$ 369
Mon 29/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 9/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/12C$ 371
Tue 9/127:35 a.m.YYC - MDW
2 stops9h 43mDelta
Sun 14/1210:49 a.m.MDW - YYC
2 stops11h 08mDelta
Deal found 8/12C$ 373
Wed 24/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 18/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/12C$ 378
Tue 30/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 5/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/12C$ 382
Tue 30/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Mon 5/14:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 7/12C$ 390

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 8 December 2025.

Round-trip from

C$ 241

One-way from

C$ 163

Popular in

December

Cheapest in

July

Average price

C$ 443

Good round-trip deal

C$ 245 or less

Good one-way deal

C$ 153 or less
Porter Airlines
  • Porter Airlines
  • 22/1-29/1
  • Nonstop
  • 3h 32m total
  • Canada to Chicago
Search Deals
Air Transat
  • Air Transat
  • 20/1
  • Nonstop
  • 1h 50m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 8 December 2025.
Use the filters below to find and compare flights from Canada to Chicago Midway Airport that are best for you.

Fly from

Canada

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 20/1

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Tue 27/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 246

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 20/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Mon 23/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 248

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 18/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 22/2

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Mon 23/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 22/2

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 18/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Mon 23/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 18/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Tue 24/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 20/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 22/2

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 21/1

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Wed 28/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 257

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 29/1

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Sun 1/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 279

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/12

Showing 1-10 of 60 results
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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$ 115). Flying from Canada to Chicago Midway Airport in December is currently the most expensive (average of C$ 286). 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 8 December 2025.

It’s optimal to fly from Canada to Chicago Midway Airport at noon. By choosing this option you can save up to 12% on the cost of your flight, compared to a flight in the evening.

How often are flights from Canada to Chicago delayed?

About 14% 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?

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 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 8 December 2025.
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
397 reviews
Check prices

Boarding

8.2

Food

7.6

Comfort

8.0

Entertainment

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
397 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Boarding

8.2

Food

7.6

Comfort

8.0

Entertainment

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Transat
7.8
Good
480 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Boarding

8.2

Food

7.6

Comfort

8.0

Entertainment

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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 Pearson Intl - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago Midway, Toronto Island - 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$ 115). Flying from Canada to Chicago Midway Airport in December is currently the most expensive (average of C$ 286). 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

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Alternative routes for Canada to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pearson Intl to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Calgary to O'Hare Intl flights
Vancouver Intl to Midway flights
Toronto Island to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Halifax to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Halifax to Midway flights
Calgary to Midway flights
Québec City to O'Hare Intl flights
Ottawa to Midway flights
Edmonton to O'Hare Intl flights
Québec City to Midway flights
Mexico City to O'Hare Intl flights
Edmonton to Midway flights
Saskatoon to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Victoria to O'Hare Intl flights
London to O'Hare Intl flights
Seattle to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Regina to O'Hare Intl flights
Kelowna to Midway flights
Detroit to O'Hare Intl flights
Buffalo to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Sudbury to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights
Victoria to Midway flights
Saskatoon to Midway flights
Nanaimo to O'Hare Intl flights
Fort McMurray to O'Hare Intl flights
St John to O'Hare Intl flights

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 8 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 196AverageC$ 393FlexibilityNo 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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