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$100+ 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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$189
(Kiwi.com)

One-way from

$100
(Delta)

Popular in

November

Cheapest in

July

Average price

$335

Good round-trip deal

$223 or less

Good one-way deal

$133 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. 4% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Thu 5/85:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 5/114:05 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 4/17$189
This Mytrip deal was found by Cheapflights users on 4/16. 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.
Sun 5/119:40 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Tue 5/203:35 pmYTZ - MDW
Nonstop1h 49mMultiple Airlines
Deal found 4/16$215
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Sun 6/229:40 amMDW - YUL
1 stop5h 20mPorter Airlines
Thu 6/2610:45 amYUL - MDW
1 stop6h 39mPorter Airlines
Deal found 4/17$236
This Delta deal was found by Cheapflights users on 4/16. 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.
Sat 5/31:16 pmMDW - YYC
1 stop8h 31mDelta
Tue 5/66:45 amYYC - MDW
1 stop9h 34mDelta
Deal found 4/16$251
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 4/305:35 pmMDW - YOW
1 stop3h 54mPorter Airlines
Thu 5/812:35 pmYOW - MDW
1 stop4h 49mPorter Airlines
Deal found 4/16$259
This Trip.com deal was found by Cheapflights users on 4/16. 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.
Fri 8/155:20 pmMDW - YTZ
Nonstop1h 42mAir Transat
Mon 8/183:35 pmYTZ - MDW
Nonstop1h 49mAir Transat
Deal found 4/16$265
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/79:16 amMDW - YYZ
1 stop4h 44mDelta
Thu 5/83:50 pmYYZ - MDW
1 stop3h 55mDelta
Deal found 4/17$267
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Sun 5/116:15 amMDW - YVR
1 stop12h 03mMultiple Airlines
Sun 5/1811:00 pmYVR - MDW
1 stop22h 47mMultiple Airlines
Deal found 4/16$279
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 6/46:40 amMDW - YYC
1 stop14h 25mMultiple Airlines
Tue 6/109:15 pmYYC - MDW
2 stops14h 40mMultiple Airlines
Deal found 4/16$280
This Trip.com deal was found by Cheapflights users on 4/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/19:40 amMDW - YUL
1 stop5h 20mMultiple Airlines
Sun 6/87:00 amYUL - MDW
1 stop15h 45mMultiple Airlines
Deal found 4/17$290
This Delta deal was found by Cheapflights users on 4/16. 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.
Sat 5/3112:48 pmMDW - YUL
1 stop10h 06mDelta
Sat 6/76:00 amYUL - MDW
1 stop3h 40mDelta
Deal found 4/16$298
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/59:20 amMDW - YEG
1 stop7h 39mDelta
Fri 9/129:25 amYEG - MDW
1 stop7h 42mDelta
Deal found 4/17$301

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 April 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

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 5/8

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Sun 5/11

4:05 pm-4:54 pm

Nonstop1h 49m

$189

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 5/11

9:40 am-12:22 pm

Nonstop1h 42m

Toronto Island

Tue 5/20

3:35 pm-4:24 pm

Nonstop1h 49m

$215

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sun 6/22

9:40 am-4:00 pm

1 stop5h 20m

Montreal Pierre Elliott Trudeau Intl

Thu 6/26

10:45 am-4:24 pm

1 stop6h 39m

$236

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 5/3

1:16 pm-8:47 pm

1 stop8h 31m

Calgary

Tue 5/6

6:45 am-5:19 pm

1 stop9h 34m

$251

ChicagoOttawa

MDW - YOW

MDWYOW

Chicago Midway

Wed 4/30

5:35 pm-10:29 pm

1 stop3h 54m

Ottawa

Thu 5/8

12:35 pm-4:24 pm

1 stop4h 49m

$259

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 5/7

9:16 am-3:00 pm

1 stop4h 44m

Toronto Pearson Intl

Thu 5/8

3:50 pm-6:45 pm

1 stop3h 55m

$267

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 7/3

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Mon 7/7

7:55 am-8:45 am

Nonstop1h 50m

$276

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Sun 5/11

6:15 am-4:18 pm

1 stop12h 03m

Vancouver Intl

Sun 5/18

11:00 pm-11:47 pm

1 stop22h 47m

$279

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 6/4

6:40 am-8:05 pm

1 stop14h 25m

Calgary

Tue 6/10

9:15 pm-12:55 pm

2 stops14h 40m

$280

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sun 6/1

9:40 am-4:00 pm

1 stop5h 20m

Montreal Pierre Elliott Trudeau Intl

Sun 6/8

7:00 am-9:45 pm

1 stop15h 45m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

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 July is currently the most expensive (average of $359). 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 April 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.

Rainfall in Canada by month

Plan your trip to Canada by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Canada ranges from 2.0 - 3.3 inches per month. June is typically the wettest month, when rainfall can reach 3.3 in. February is typically the driest time to visit Canada when rainfall is around 2.0 in.

Temperature in Canada by month

Plan your trip to Canada by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Canada, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

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 April 17, 2025.
Read reviews from past customers who have flown Porter Airlines, Delta and Air Transat from Chicago to Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
281 reviews

Entertainment

7.0

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
281 reviews
Porter Airlines
8.0
Very good
281 reviews

Entertainment

7.0

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,916 reviews
Porter Airlines
8.0
Very good
281 reviews

Entertainment

7.0

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Transat
7.8
Good
385 reviews
Porter Airlines
8.0
Very good
281 reviews

Entertainment

7.0

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,809 reviews
Porter Airlines
8.0
Very good
281 reviews

Entertainment

7.0

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Frontier
6.0
Okay
3,281 reviews
Porter Airlines
8.0
Very good
281 reviews

Entertainment

7.0

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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.

  • 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 $100 on Delta. Other airlines that offer cheap prices include Porter Airlines from $105 and Air Transat from $112 one-way.

  • What are the most popular routes from Chicago Midway Airport to Canada?

    Most travelers choose Chicago Midway - Vancouver Intl, Chicago Midway - Montreal Pierre Elliott Trudeau Intl or Chicago Midway - Calgary 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 July is currently the most expensive (average of $359). 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

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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 Orlando 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$218Average$377FlexibilityNo cancel feeOn-time52%

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