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$55+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Booking.com deal was found by Cheapflights users on 12/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 1/69:20 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/16$389
This FlightHub deal was found by Cheapflights users on 12/16. 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.
Tue 12/304:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 1/29:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/16$408
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/316:08 pmMDW - YYZ
1 stop16h 11mWestJet
Mon 1/510:05 amYYZ - MDW
1 stop3h 43mWestJet
Deal found 12/16$416
This Delta deal was found by Cheapflights users on 12/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:08 pmMDW - YUL
1 stop4h 11mDelta
Mon 1/57:00 amYUL - MDW
1 stop10h 29mDelta
Deal found 12/16$422
This Trip.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/3111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 1/59:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/16$422
This KAYAK deal was found by Cheapflights users on 12/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2311:48 amMDW - YYC
1 stop10h 18mDelta
Thu 1/86:30 amYYC - MDW
1 stop5h 39mDelta
Deal found 12/16$425
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/316:08 pmMDW - YYZ
1 stop16h 11mMultiple Airlines
Mon 1/58:30 pmYYZ - MDW
2 stops50h 47mMultiple Airlines
Deal found 12/16$431
This Trip.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 1/52:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/16$433
This FlightHub deal was found by Cheapflights users on 12/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 12/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/15$435
This Trip.com deal was found by Cheapflights users on 12/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/254:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 12/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/15$437
This FlightHub deal was found by Cheapflights users on 12/16. 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 12/254:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 1/119:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/16$441
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Tue 12/234:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 12/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/16$445

Find flight deals from Midway to Canada

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

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$186
(Trip.com)

One-way from

$55
(Trip.com)

Popular in

January

Cheapest in

September

Average price

$301

Good round-trip deal

$243 or less

Good one-way deal

$126 or less
Provider with most accurate pricing for Chicago (CHI)-Toronto (YTO) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Toronto (YTO) flights.
Search Deals
From Chicago Midway to Canada
Search Deals
One-way flight from Chicago Midway to Canada
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 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 Chicago Midway to Canada.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Canada.
Search Deals

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 December 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

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 1/22

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Mon 1/26

9:20 am-10:10 am

Nonstop1h 50m

$191

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 1/16

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Sun 1/18

2:30 pm-3:20 pm

Nonstop1h 50m

$197

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 1/16

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Fri 1/23

9:15 am-10:05 am

Nonstop1h 50m

$204

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 1/22

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Sun 1/25

2:30 pm-3:20 pm

Nonstop1h 50m

$205

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 1/30

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sat 1/31

11:00 am-11:50 am

Nonstop1h 50m

$210

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 1/31

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Sat 2/7

11:00 am-11:50 am

Nonstop1h 50m

$215

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 1/26

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Tue 1/27

9:20 am-10:10 am

Nonstop1h 50m

$226

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 1/17

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Sun 1/18

9:15 am-10:05 am

Nonstop1h 50m

$230

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 2/10

1:51 pm-11:13 pm

1 stop8h 22m

Toronto Pearson Intl

Fri 2/13

10:05 am-5:37 pm

1 stop8h 32m

$234

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 2/5

9:53 am-3:59 pm

1 stop5h 06m

Toronto Pearson Intl

Mon 2/9

10:05 am-12:46 pm

1 stop3h 41m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Canada (average of $79). Flying from Chicago Midway Airport to Canada in January is currently the most expensive (average of $333). 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 December 18, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 32% on flights from Chicago Midway Airport to Canada by exploring options for tickets in the evening.

How often are flights from Chicago to Canada delayed?

About 15% of weekly flights between Chicago and Canada have experienced delays in the past year, with the average delay time being 116 minutes.

What is the most punctual flight time for Chicago to Canada flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday 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 Chicago to Canada flights?

Over the last year, Porter Airlines have had the lowest number of delays on this route, with just 13% of flights being delayed.

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 December 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
399 reviews

Crew

8.6

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

Comfort

7.9

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
399 reviews
Porter Airlines
8.0
Very good
399 reviews

Crew

8.6

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

Comfort

7.9

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 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 $191, Porter Airlines can have you in Canada from Chicago Midway Airport in 1h 42m. The distance between Chicago Midway Airport and Canada is about 442 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 Pearson Intl, Chicago Midway - Toronto Island 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Canada (average of $79). Flying from Chicago Midway Airport to Canada in January is currently the most expensive (average of $333). 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$185Average$353FlexibilityNo cancel feeOn-time52%

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