HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Canada

$62+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Canada with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 20, 2026.

This FlightHub deal was found by Cheapflights users on 1/19. 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.
Sat 2/1412:50 pm
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Tue 2/179:20 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/19$191
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/1911:05 am
MDW
-
YUL
1 stop4h 25m
Porter Airlines
Mon 2/236:45 am
YUL
-
MDW
1 stop4h 25m
Porter Airlines
Deal found 1/19$195
This oojo deal was found by Cheapflights users on 1/18. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/911:05 am
MDW
-
YUL
1 stop5h 40m
Porter Airlines
Sat 2/148:55 am
YUL
-
MDW
1 stop4h 00m
Porter Airlines
Deal found 1/18$197
This Trip.com deal was found by Cheapflights users on 1/19. 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.
Tue 2/2411:05 am
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Fri 2/279:20 am
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 1/19$198
This Trip.com deal was found by Cheapflights users on 1/19. 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.
Sat 2/1412:50 pm
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Sat 2/2111:05 am
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 1/19$200
This Trip.com deal was found by Cheapflights users on 1/19. 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 2/1211:05 am
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sun 2/152:30 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/19$201
This FlightHub deal was found by Cheapflights users on 1/20. 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 2/1911:05 am
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Thu 2/269:20 am
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 1/20$203
This Kiwi.com deal was found by Cheapflights users on 1/18. 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 2/2611:05 am
MDW
-
YUL
1 stop5h 40m
Porter Airlines
Wed 3/46:45 am
YUL
-
MDW
1 stop4h 20m
Porter Airlines
Deal found 1/18$212
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/511:05 am
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sun 2/82:30 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/19$214
This FlightHub deal was found by Cheapflights users on 1/20. 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 2/1211:05 am
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Tue 2/179:20 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/20$215
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/511:05 am
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Mon 2/99:20 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/19$217
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/611:05 am
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sun 2/82:30 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/19$227

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 January 20, 2026.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$191
(FlightHub)

One-way from

$62
(Trip.com)

Popular in

January

Cheapest in

September

Average price

$309

Good round-trip deal

$235 or less

Good one-way deal

$270 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. 12% 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 January 2026
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 January 20, 2026.
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

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Mon 2/9

11:05 am-5:45 pm

1 stop5h 40m

Montreal Pierre Elliott Trudeau Intl

Sat 2/14

8:55 am-11:55 am

1 stop4h 00m

$197

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 2/23

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Wed 2/25

9:20 am-10:10 am

Nonstop1h 50m

$200

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 2/12

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Sun 2/15

2:30 pm-3:20 pm

Nonstop1h 50m

$201

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 2/26

11:05 am-5:45 pm

1 stop5h 40m

Montreal Pierre Elliott Trudeau Intl

Wed 3/4

6:45 am-10:05 am

1 stop4h 20m

$212

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 2/12

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Tue 2/17

9:20 am-10:10 am

Nonstop1h 50m

$215

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 2/22

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Fri 2/27

9:20 am-10:10 am

Nonstop1h 50m

$230

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 2/22

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Tue 2/24

9:20 am-10:10 am

Nonstop1h 50m

$230

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 2/22

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Wed 2/25

9:20 am-10:10 am

Nonstop1h 50m

$230

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 2/23

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Sat 2/28

11:05 am-11:55 am

Nonstop1h 50m

$232

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 2/6

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Sun 2/8

2:30 pm-3:20 pm

Nonstop1h 50m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 60 results
1
2
3
...
6

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 November is currently the most expensive (average of $289). 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 January 20, 2026.

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.

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 119 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 at night tend to experience delays more often.

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

Thursday 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 January 20, 2026.
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
412 reviews

Crew

8.6

Food

7.5

Comfort

7.9

Entertainment

6.9

Overall

7.9

Boarding

8.2

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
7.9
Good
412 reviews
Porter Airlines
7.9
Good
412 reviews

Crew

8.6

Food

7.5

Comfort

7.9

Entertainment

6.9

Overall

7.9

Boarding

8.2

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 $197, Porter Airlines can have you in Canada from Chicago Midway Airport in 5h 40m. The distance between Chicago Midway Airport and Canada is about 743 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 - Vancouver Intl, Chicago Midway - Toronto Pearson Intl or Chicago Midway - Toronto Island 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 November is currently the most expensive (average of $289). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Canada

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Orlando flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Seattle flights
O'Hare Intl to Denver flights
O'Hare Intl to Tampa flights
O'Hare Intl to San Francisco flights
Midway to Cancún flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to West Palm Beach flights
Midway to Miami flights
O'Hare Intl to Newark flights
Midway to Las Vegas flights
O'Hare Intl to Santa Ana flights
Midway to Orlando flights
Midway to Sky Harbor Intl flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Honolulu flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Ontario flights
O'Hare Intl to Cozumel flights
Midway to Fort Lauderdale flights
O'Hare Intl to Sarasota flights
Midway to Los Angeles flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Austin flights
O'Hare Intl to Baltimore flights
O'Hare Intl to San Diego flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Charleston flights
O'Hare Intl to San José del Cabo flights
Midway to Mexico City flights
O'Hare Intl to George Bush Intcntl flights
Midway to Tampa flights
Midway to Fort Myers flights
O'Hare Intl to Key West flights
Midway to Newark flights
O'Hare Intl to Vancouver Intl flights
O'Hare Intl to Hobby flights
Midway to John F Kennedy Intl flights

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 January 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$172Average$288FlexibilityNo cancel feeOn-time52%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.