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Cheap flights from Canada to Chicago Midway Airport from C$ 172

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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
24 Dec — 31 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Canada to Midway

Keep the following information in mind while searching for Canada to Midway flight deals. Data was last updated 24 November 2025.

Round-trip from

C$ 255

One-way from

C$ 172

Popular in

November

Cheapest in

July

Average price

C$ 409

Good round-trip deal

C$ 348 or less

Good one-way deal

C$ 199 or less
Porter Airlines
  • Porter Airlines
  • 5/1-6/1
  • Nonstop
  • 3h 32m total
  • Canada to Chicago
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9/1
  • 9/1
  • 2 total stops
  • 26h 12m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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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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Find 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 24 November 2025.

Fri 19/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 29/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/11C$ 257
Wed 31/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/11C$ 262
Tue 23/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 4/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 23/11C$ 266
Tue 30/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/11C$ 268
Mon 22/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 29/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/11C$ 269
Tue 23/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 1/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 23/11C$ 271
Wed 24/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 30/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/11C$ 272
Mon 8/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 11/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/11C$ 274
Fri 12/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 15/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 23/11C$ 275
Fri 5/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 7/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 21/11C$ 278
Fri 12/1212:13 p.m.YYZ - MDW
1 stop6h 47mDelta
Tue 16/126:40 p.m.MDW - YYZ
1 stop3h 31mDelta
Deal found 23/11C$ 300
Sat 6/1210:05 a.m.YYZ - MDW
1 stop3h 29mDelta
Sat 13/121:14 p.m.MDW - YYZ
1 stop3h 01mDelta
Deal found 22/11C$ 312

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 24 November 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

Wed 7/1

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

Nonstop1h 50m

Chicago Midway

Wed 14/1

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

Nonstop1h 42m

C$ 255

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 19/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Mon 29/12

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

Nonstop1h 42m

C$ 257

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 23/12

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

Nonstop1h 50m

Chicago Midway

Thu 1/1

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

Nonstop1h 42m

C$ 257

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 23/12

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

Nonstop1h 50m

Chicago Midway

Sun 4/1

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

Nonstop1h 42m

C$ 266

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 30/12

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

Nonstop1h 50m

Chicago Midway

Thu 1/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 23/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sat 3/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 23/12

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

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

Nonstop1h 42m

C$ 271

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 4/1

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

Nonstop1h 50m

Chicago Midway

Tue 6/1

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

Nonstop1h 42m

C$ 272

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 8/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Thu 11/12

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

Nonstop1h 42m

C$ 274

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 22/12

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

Nonstop1h 50m

Chicago Midway

Mon 29/12

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

Nonstop1h 42m

C$ 283

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/11

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$ 117). Flying from Canada to Chicago Midway Airport in December is currently the most expensive (average of C$ 306). 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 24 November 2025.

It’s optimal to fly from Canada to Chicago Midway Airport at noon. By choosing this option you can save up to 6% on the cost of your flight, compared to a flight in the evening.

What is the cheapest day to fly from Canada to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Canada to Midway. Price data was last updated on 16 December 2024.

Travelers seeking maximum savings on their Canada to Chicago Midway Airport flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 106 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, Contour has had the lowest number of delays on this route, with no flights being classified as 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 24 November 2025.
Check out reviews from past customers who have flown with Porter Airlines,Air Transat, andWestJet 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
393 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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
393 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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
478 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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
WestJet
7.2
Good
3,172 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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 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$ 117). Flying from Canada to Chicago Midway Airport in December is currently the most expensive (average of C$ 306). 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
Pearson Intl to Midway flights
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Ottawa to O'Hare Intl flights
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Calgary to Midway flights
Edmonton to O'Hare Intl flights
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Edmonton to Midway flights
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Kelowna to Midway flights
Saskatoon to Midway flights
Victoria to O'Hare Intl flights
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Hamilton to O'Hare Intl flights
St. John's to O'Hare Intl flights
Buffalo to O'Hare Intl flights
Regina to O'Hare Intl flights
Victoria to Midway flights
London to O'Hare Intl flights
Fort McMurray to O'Hare Intl flights
Sudbury to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights

Top 2 airlines flying from Canada to Midway

Discover the top 2 airlines 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 24 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 199AverageC$ 400FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 560AverageC$ 691FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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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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