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$106+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
Sep 1 — Sep 81
Tue 9/1
Tue 9/8
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 August 2, 2026.

This oojo deal was found by Cheapflights users on 7/28. 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.
Wed 9/211:45 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sat 9/51:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/28$236
This Super.com deal was found by Cheapflights users on 7/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/33:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Tue 9/81:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/28$238
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 10/511:45 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sat 10/101:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 8/1$241
This Super.com deal was found by Cheapflights users on 7/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Fri 8/288:55 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/29$242
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Sun 8/2310:20 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Thu 9/31:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 8/2$243
This Trip.com deal was found by Cheapflights users on 7/30. 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 8/193:15 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Thu 8/278:55 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/30$244
This Porter Airlines deal was found by Cheapflights users on 7/29. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:45 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sat 9/1910:10 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/29$245
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 8/2210:20 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Wed 9/210:10 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 8/2$246
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 9/33:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Fri 9/1110:10 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/28$247
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Tue 8/258:55 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/31$248
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/3110:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Mon 9/710:10 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/28$249
This Trip.com deal was found by Cheapflights users on 7/29. 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 8/263:15 pm
MDW
-
YTZ
Nonstop1h 40m
Multiple Airlines
Wed 9/21:45 pm
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 7/29$250

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 August 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$236
(oojo)

One-way from

$106
(Porter Airlines)

Popular in

August

Cheapest in

March

Average price

$311

Good round-trip deal

$238 or less

Good one-way deal

$147 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. 3% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 August 2, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Canada that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 9/12

11:45 am-2:25 pm

Nonstop1h 40m

Toronto Island

Sat 9/19

10:10 am-11:00 am

Nonstop1h 50m

$245

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 9/12

11:45 am-2:25 pm

Nonstop1h 40m

Toronto Island

Tue 9/15

1:45 pm-2:35 pm

Nonstop1h 50m

$245

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 8/22

10:20 am-1:00 pm

Nonstop1h 40m

Toronto Island

Tue 8/25

1:45 pm-2:35 pm

Nonstop1h 50m

$261

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 10/9

9:29 am-5:19 pm

1 stop6h 50m

Toronto Pearson Intl

Mon 10/12

6:00 am-12:47 pm

1 stop7h 47m

$266

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 9/11

9:29 am-5:20 pm

1 stop6h 51m

Toronto Pearson Intl

Fri 9/18

12:08 pm-6:33 pm

1 stop7h 25m

$266

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 9/3

1:25 pm-11:03 pm

1 stop8h 38m

Toronto Pearson Intl

Tue 9/8

12:08 pm-4:57 pm

1 stop5h 49m

$266

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 9/8

9:29 am-5:20 pm

1 stop6h 51m

Toronto Pearson Intl

Wed 9/16

6:00 am-12:39 pm

1 stop7h 39m

$266

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 10/24

6:44 pm-10:56 pm

1 stop3h 12m

Toronto Pearson Intl

Tue 10/27

6:00 am-12:47 pm

1 stop7h 47m

$266

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 10/10

6:44 pm-10:56 pm

1 stop3h 12m

Toronto Pearson Intl

Mon 10/12

6:00 am-12:47 pm

1 stop7h 47m

$266

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 8/24

6:42 pm-11:03 pm

1 stop3h 21m

Toronto Pearson Intl

Fri 8/28

12:09 pm-6:33 pm

1 stop7h 24m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 60 resultsSorted by cheapest first
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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 $205). Flying from Chicago Midway Airport to Canada in February is currently the most expensive (average of $656). 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 2, 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 16% of weekly flights between Chicago and Canada have experienced delays in the past year, with the average delay time being 114 minutes.

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

Historically, flights departing in the evening 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?

Saturday 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 15% 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 August 2, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Canada, such as Porter Airlines and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
449 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

6.9

Food

7.5

Comfort

8.0

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Porter Airlines
8.0
Very good
449 reviews
Porter Airlines
8.0
Very good
449 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

6.9

Food

7.5

Comfort

8.0

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Delta
7.8
Good
8,494 reviews
Porter Airlines
8.0
Very good
449 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

6.9

Food

7.5

Comfort

8.0

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

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 $245, Porter Airlines can have you in Canada from Chicago Midway Airport in 1h 40m. 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Canada (average of $205). Flying from Chicago Midway Airport to Canada in February is currently the most expensive (average of $656). 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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Midway to San Francisco flights

Top 2 airlines flying from Midway to Canada

Discover the top 2 airlines 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 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$88Average$359FlexibilityNo cancel feeOn-timeN/A
Porter AirlinesCheapest$174Average$292FlexibilityNo cancel feeOn-time52%

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