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$53+ Cheap flights from Midway (MDW) to Canada

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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Midway to Canada

Keep the following information in mind while searching for Midway to Canada flight deals. Data was last updated August 18, 2025.

Round-trip from

$149
(Mytrip)

One-way from

$53
(Kiwi.com)

Popular in

November

Cheapest in

July

Average price

$274

Good round-trip deal

$172 or less

Good one-way deal

$91 or less
From Chicago Midway to Canada
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One-way flight from Chicago Midway to Canada
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Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 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 Chicago Midway to Canada.
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Price to beat on a one-way flight from Chicago Midway to Canada.
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Find flight deals from Midway to Canada

Cheapest flights from Midway to Canada
Explore the most affordable flight options available from Midway to Canada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This Mytrip deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/139:35 amMDW - YQB
1 stop5h 20mPorter Airlines
Mon 9/1511:00 amYQB - MDW
1 stop6h 24mPorter Airlines
Deal found 8/17$149
This Mytrip deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/129:35 amMDW - YQB
1 stop5h 20mPorter Airlines
Mon 9/1511:00 amYQB - MDW
1 stop6h 24mPorter Airlines
Deal found 8/17$155
This KAYAK deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/19:35 amMDW - YQB
1 stop5h 20mPorter Airlines
Sun 10/511:00 amYQB - MDW
1 stop6h 24mPorter Airlines
Deal found 8/17$165
This FlightHub deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/59:35 amMDW - YQB
1 stop5h 20mPorter Airlines
Mon 9/811:00 amYQB - MDW
1 stop6h 24mPorter Airlines
Deal found 8/16$186
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/19:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 10/87:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/17$193
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/125:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 9/173:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/17$195
This Trip.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/25:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 10/57:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/16$196
This Trip.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/125:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 9/157:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/16$199
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/105:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 9/147:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/16$200
This FlightHub deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/259:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 9/293:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/16$208
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/59:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 9/67:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 8/16$211
This SmartFares deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2911:00 amMDW - YHZ
1 stop7h 05mPorter Airlines
Sun 12/78:25 amYHZ - MDW
2 stops8h 55mPorter Airlines
Deal found 8/17$217

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Canada 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 2,558,603 searches. Data last updated August 18, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Canada that are best for you.

Fly from

Midway

Fly to

Canada

Route

Depart

Return

Price

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Sat 9/13

9:35 am-3:55 pm

1 stop5h 20m

Québec City

Mon 9/15

11:00 am-4:24 pm

1 stop6h 24m

$149

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Fri 9/12

9:35 am-3:55 pm

1 stop5h 20m

Québec City

Mon 9/15

11:00 am-4:24 pm

1 stop6h 24m

$155

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Wed 10/1

9:35 am-3:55 pm

1 stop5h 20m

Québec City

Sun 10/5

11:00 am-4:24 pm

1 stop6h 24m

$165

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Fri 9/5

9:35 am-3:55 pm

1 stop5h 20m

Québec City

Mon 9/8

11:00 am-4:24 pm

1 stop6h 24m

$186

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 10/1

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Wed 10/8

7:50 am-8:39 am

Nonstop1h 49m

$193

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 9/12

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Thu 9/18

3:35 pm-4:24 pm

Nonstop1h 49m

$195

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 9/20

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Wed 9/24

3:35 pm-4:24 pm

Nonstop1h 49m

$195

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 9/16

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Sat 9/20

7:50 am-8:39 am

Nonstop1h 49m

$195

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 9/26

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Mon 9/29

7:50 am-8:39 am

Nonstop1h 49m

$195

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 9/21

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 9/28

7:50 am-8:39 am

Nonstop1h 49m

$195

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 60 results
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Best time to book a flight from Midway to Canada

Have a flexible travel schedule? Discover the best time to fly to Canada from Midway 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 Chicago Midway Airport to Canada

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Canada (average of $243). Flying from Chicago Midway Airport to Canada in August is currently the most expensive (average of $348). 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 MDW to CA?

Find hourly flight availability from Midway to Canada. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 18, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Canada as you normally would.

Reviews of airlines servicing Canada

Get insights into the airlines that provide service to Canada. 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 Canada. Reviews last updated August 18, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Canada, such as Porter Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
333 reviews

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.7

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
8.0
Very good
333 reviews
Porter Airlines
8.0
Very good
333 reviews

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.7

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 Midway to Canada. 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 Chicago Midway Airport to Canada?

    For as low as $149, Porter Airlines can have you in Canada from Chicago Midway Airport in 5h 20m. The distance between Chicago Midway Airport and Canada is about 877 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Chicago Midway Airport to Canada?

    Most travelers choose Chicago Midway - Toronto Island, Chicago Midway - Toronto Pearson Intl or Chicago Midway - Montreal Pierre Elliott Trudeau Intl when deciding on the best route from Chicago Midway Airport to Canada.

  • Can I find deals for flights from Midway to Canada that include hotel bookings?

    Yes. In addition to deals on Midway to Canada flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Canada?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Canada.

  • Can I find deals for business class flights from Midway to Canada?

    Yes. Cheapflights offers flight deals from Midway to Canada 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 Chicago Midway Airport to Canada?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Canada (average of $243). Flying from Chicago Midway Airport to Canada in August is currently the most expensive (average of $348). 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 Midway to Canada

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Midway to Canada

Discover the top airline that operate flights from Midway to Canada. 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 2,558,603 searches. Data last updated August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$187Average$324FlexibilityNo cancel feeOn-time52%

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