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Cheap flights from Canada to Chicago Midway Airport from C$ 134

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 25/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
31 Aug — 7 Sep1
1 adult

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 26 August 2025.

Round-trip from

C$ 181

One-way from

C$ 134

Popular in

December

Cheapest in

July

Average price

C$ 386

Good round-trip deal

C$ 241 or less

Good one-way deal

C$ 205 or less
Porter Airlines
  • Porter Airlines
  • 18/9-21/9
  • 2 total stops
  • 11h 44m total
  • Canada to Chicago
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Porter Airlines
  • Porter Airlines
  • 25/9
  • 1 total stop
  • 6h 24m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 37 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 7 potential savings vs. average RT price).
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Average for round-trip flights in August 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

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 August 2025.

Thu 18/911:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Sun 21/99:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Deal found 26/8C$ 181
Thu 2/1011:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Sat 4/109:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Deal found 25/8C$ 197
Fri 3/1011:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Sat 4/109:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Deal found 25/8C$ 202
Thu 11/911:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Sat 13/99:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Deal found 25/8C$ 209
Fri 5/911:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Mon 8/99:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Deal found 25/8C$ 226
Fri 5/911:00 a.m.YQB - MDW
1 stop6h 24mPorter Airlines
Sat 6/99:35 a.m.MDW - YQB
1 stop5h 20mPorter Airlines
Deal found 25/8C$ 234
Thu 2/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 5/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/8C$ 235
Fri 19/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 21/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 25/8C$ 238
Sun 21/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 28/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/8C$ 241
Fri 26/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 29/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/8C$ 244
Sat 20/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Tue 30/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 25/8C$ 246
Thu 18/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Thu 9/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/8C$ 249

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 August 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

Québec CityChicago

YQB - MDW

YQBMDW

Québec City

Fri 17/10

11:00 a.m.-4:24 p.m.

1 stop6h 24m

Chicago Midway

Sun 19/10

9:35 a.m.-3:55 p.m.

1 stop5h 20m

C$ 181

Québec CityChicago

YQB - MDW

YQBMDW

Québec City

Thu 18/9

11:00 a.m.-4:24 p.m.

1 stop6h 24m

Chicago Midway

Sun 21/9

9:35 a.m.-3:55 p.m.

1 stop5h 20m

C$ 181

Québec CityChicago

YQB - MDW

YQBMDW

Québec City

Sun 12/10

11:00 a.m.-4:24 p.m.

1 stop6h 24m

Chicago Midway

Sat 18/10

9:35 a.m.-3:55 p.m.

1 stop5h 20m

C$ 197

Québec CityChicago

YQB - MDW

YQBMDW

Québec City

Thu 2/10

11:00 a.m.-4:24 p.m.

1 stop6h 24m

Chicago Midway

Sat 4/10

9:35 a.m.-3:55 p.m.

1 stop5h 20m

C$ 197

Québec CityChicago

YQB - MDW

YQBMDW

Québec City

Fri 24/10

11:00 a.m.-4:24 p.m.

1 stop6h 24m

Chicago Midway

Sat 25/10

9:35 a.m.-3:55 p.m.

1 stop5h 20m

C$ 197

Québec CityChicago

YQB - MDW

YQBMDW

Québec City

Fri 3/10

11:00 a.m.-4:24 p.m.

1 stop6h 24m

Chicago Midway

Sat 4/10

9:35 a.m.-3:55 p.m.

1 stop5h 20m

C$ 202

Québec CityChicago

YQB - MDW

YQBMDW

Québec City

Thu 11/9

11:00 a.m.-4:24 p.m.

1 stop6h 24m

Chicago Midway

Sat 13/9

9:35 a.m.-3:55 p.m.

1 stop5h 20m

C$ 209

Québec CityChicago

YQB - MDW

YQBMDW

Québec City

Fri 19/9

11:00 a.m.-4:24 p.m.

1 stop6h 24m

Chicago Midway

Mon 22/9

9:35 a.m.-3:55 p.m.

1 stop5h 20m

C$ 226

Québec CityChicago

YQB - MDW

YQBMDW

Québec City

Fri 5/9

11:00 a.m.-4:24 p.m.

1 stop6h 24m

Chicago Midway

Mon 8/9

9:35 a.m.-3:55 p.m.

1 stop5h 20m

C$ 226

Québec CityChicago

YQB - MDW

YQBMDW

Québec City

Fri 5/9

11:00 a.m.-4:24 p.m.

1 stop6h 24m

Chicago Midway

Sat 6/9

9:35 a.m.-3:55 p.m.

1 stop5h 20m

C$ 234

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/8

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, September is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 232). Flying from Canada to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 August 2025.

When flying from Canada to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 August 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
7.9
Good
347 reviews
Check prices

Comfort

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
7.9
Good
347 reviews
Porter Airlines
7.9
Good
347 reviews
Check prices

Comfort

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Transat
7.7
Good
428 reviews
Porter Airlines
7.9
Good
347 reviews
Check prices

Comfort

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
3,055 reviews
Porter Airlines
7.9
Good
347 reviews
Check prices

Comfort

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Boarding

8.2

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 6h 24m. The distance from Canada to Chicago Midway Airport is about 1411 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, September is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 232). Flying from Canada to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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.
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Pearson Intl to Midway flights
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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 26 August 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 203AverageC$ 452FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 421AverageC$ 603FlexibilityNo 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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