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$70+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$171
(Kiwi.com)

One-way from

$70
(Mytrip)

Popular in

November

Cheapest in

July

Average price

$258

Good round-trip deal

$196 or less

Good one-way deal

$88 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. 6% potential increase in price ($19 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 September 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 September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/189:35 amMDW - YQB
1 stop5h 20mPorter Airlines
Thu 10/2311:00 amYQB - MDW
1 stop6h 24mPorter Airlines
Deal found 9/15$171
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Mon 10/209:35 amMDW - YQB
1 stop5h 20mPorter Airlines
Thu 10/2311:00 amYQB - MDW
1 stop6h 24mPorter Airlines
Deal found 9/15$173
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/69:35 amMDW - YQB
1 stop5h 20mPorter Airlines
Fri 10/1711:00 amYQB - MDW
1 stop6h 24mPorter Airlines
Deal found 9/16$175
This Mytrip deal was found by Cheapflights users on 9/15. 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.
Sun 10/129:35 amMDW - YQB
1 stop5h 20mPorter Airlines
Thu 10/1611:00 amYQB - MDW
1 stop6h 24mPorter Airlines
Deal found 9/15$177
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/122:06 pmMDW - YVR
1 stop23h 06mMultiple Airlines
Tue 11/187:45 pmYVR - MDW
2 stops14h 56mMultiple Airlines
Deal found 9/15$203
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/158:05 amMDW - YVR
1 stop14h 43mMultiple Airlines
Wed 10/228:30 pmYVR - MDW
2 stops21h 51mMultiple Airlines
Deal found 9/15$206
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2511:00 amMDW - YHZ
1 stop7h 05mPorter Airlines
Mon 12/18:30 amYHZ - MDW
1 stop8h 50mPorter Airlines
Deal found 9/16$208
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/46:15 amMDW - YVR
1 stop16h 33mMultiple Airlines
Tue 10/79:30 amYVR - MDW
1 stop26h 08mMultiple Airlines
Deal found 9/15$211
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/306:20 amMDW - YWG
2 stops18h 21mMultiple Airlines
Fri 10/317:30 amYWG - MDW
1 stop11h 09mMultiple Airlines
Deal found 9/15$216
This Booking.com deal was found by Cheapflights users on 9/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3011:00 amMDW - YHZ
1 stop7h 05mPorter Airlines
Thu 11/68:30 amYHZ - MDW
1 stop8h 50mPorter Airlines
Deal found 9/15$220
This Mytrip deal was found by Cheapflights users on 9/14. 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 10/49:35 amMDW - YHZ
2 stops12h 05mPorter Airlines
Wed 10/86:10 amYHZ - MDW
2 stops12h 14mPorter Airlines
Deal found 9/14$224
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/159:35 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Wed 10/2212:00 pmYTZ - MDW
2 stops22h 47mMultiple Airlines
Deal found 9/17$230

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 September 17, 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

Sun 10/19

9:35 am-3:55 pm

1 stop5h 20m

Québec City

Thu 10/23

11:00 am-4:24 pm

1 stop6h 24m

$171

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Mon 10/6

9:35 am-3:55 pm

1 stop5h 20m

Québec City

Fri 10/17

11:00 am-4:24 pm

1 stop6h 24m

$175

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Sun 10/12

9:35 am-3:55 pm

1 stop5h 20m

Québec City

Thu 10/16

11:00 am-4:24 pm

1 stop6h 24m

$177

ChicagoHalifax

MDW - YHZ

MDWYHZ

Chicago Midway

Tue 11/25

11:00 am-8:05 pm

1 stop7h 05m

Halifax Intl

Mon 12/1

8:30 am-3:20 pm

1 stop8h 50m

$208

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 10/30

6:20 am-12:41 am

2 stops18h 21m

Winnipeg

Fri 10/31

7:30 am-6:39 pm

1 stop11h 09m

$216

ChicagoHalifax

MDW - YHZ

MDWYHZ

Chicago Midway

Sat 10/11

9:35 am-11:40 pm

2 stops12h 05m

Halifax Intl

Thu 10/16

6:10 am-4:24 pm

2 stops12h 14m

$232

ChicagoQuébec City

MDW - YQB

MDWYQB

Chicago Midway

Sun 10/19

9:35 am-3:55 pm

1 stop5h 20m

Québec City

Fri 10/24

11:00 am-4:24 pm

1 stop6h 24m

$238

ChicagoHalifax

MDW - YHZ

MDWYHZ

Chicago Midway

Wed 11/26

11:00 am-8:05 pm

1 stop7h 05m

Halifax Intl

Mon 12/1

8:30 am-3:20 pm

1 stop8h 50m

$239

ChicagoHalifax

MDW - YHZ

MDWYHZ

Chicago Midway

Thu 10/30

11:00 am-7:51 pm

2 stops6h 51m

Halifax Intl

Thu 11/6

8:25 am-3:20 pm

2 stops8h 55m

$241

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Tue 10/14

8:05 am-8:48 pm

1 stop14h 43m

Vancouver Intl

Tue 10/21

9:30 am-1:38 pm

1 stop26h 08m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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 September 17, 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 September 17, 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
7.9
Good
365 reviews

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Crew

8.6

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
365 reviews
Porter Airlines
7.9
Good
365 reviews

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Crew

8.6

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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 $171, 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 cheapest airlines to fly from Chicago Midway Airport to Canada one-way?

    One-way options have recently been found by users for as low as $70 on Porter Airlines. Other airlines that offer cheap prices include Delta from $100 and WestJet from $131 one-way.

  • 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 - Vancouver 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$187Average$355FlexibilityNo cancel feeOn-time52%

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