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$79+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
Dec 10 — Dec 171
Wed 12/10
Wed 12/17
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 November 10, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$187
(Kiwi.com)

One-way from

$79
(Trip.com)

Popular in

November

Cheapest in

September

Average price

$348

Good round-trip deal

$287 or less

Good one-way deal

$210 or less
Provider with most accurate pricing for Chicago (CHI)-Toronto (YTO) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Toronto (YTO) flights.
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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. 9% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 10, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/8. 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 11/234:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 12/29:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/8$187
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 11/284:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 12/12:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$192
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 12/92:49 pmMDW - YWG
1 stop24h 18mMultiple Airlines
Sun 12/147:30 amYWG - MDW
1 stop26h 22mMultiple Airlines
Deal found 11/8$192
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 11/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 11/279:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$196
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 11/2511:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 11/282:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/8$202
This Trip.com deal was found by Cheapflights users on 11/8. 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 11/2212:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 11/239:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/8$203
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 12/88:42 pmMDW - YWG
2 stops21h 24mMultiple Airlines
Fri 12/127:30 amYWG - MDW
1 stop14h 42mMultiple Airlines
Deal found 11/8$203
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 11/234:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 12/42:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$204
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 1/69:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$205
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 1/59:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$207
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/254:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 1/69:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$208
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/3111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 1/59:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$209

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 November 10, 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

Tue 12/2

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 12/7

9:15 am-10:05 am

Nonstop1h 50m

$192

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 12/31

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Mon 1/5

9:15 am-10:05 am

Nonstop1h 50m

$209

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 12/31

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Tue 1/6

9:15 am-10:05 am

Nonstop1h 50m

$209

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 1/16

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Fri 1/30

9:15 am-10:05 am

Nonstop1h 50m

$210

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 11/25

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Fri 11/28

2:30 pm-3:20 pm

Nonstop1h 50m

$210

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 12/2

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Thu 12/4

2:30 pm-3:20 pm

Nonstop1h 50m

$214

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 12/5

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Sun 12/7

9:15 am-10:05 am

Nonstop1h 50m

$219

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Thu 12/4

6:15 am-10:45 pm

2 stops18h 30m

Vancouver Intl

Sun 12/7

11:00 pm-8:46 am

1 stop31h 46m

$220

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 12/4

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 12/7

9:15 am-10:05 am

Nonstop1h 50m

$220

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 12/12

6:15 am-3:07 pm

1 stop8h 52m

Winnipeg

Sun 12/14

7:30 am-9:52 am

1 stop26h 22m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/8

Showing 1-10 of 60 results
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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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Canada (average of $135). Flying from Chicago Midway Airport to Canada in March is currently the most expensive (average of $473). 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 November 10, 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.

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 November 10, 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
388 reviews

Overall

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
388 reviews
Porter Airlines
8.0
Very good
388 reviews

Overall

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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 $192, 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 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 $86 on Porter Airlines. Other airlines that offer cheap prices include Delta from $89 and Air Transat from $110 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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Canada (average of $135). Flying from Chicago Midway Airport to Canada in March is currently the most expensive (average of $473). 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 November 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$185Average$348FlexibilityNo cancel feeOn-time52%

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