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Midway

$121+ Cheap flights from Canada to Midway (MDW)

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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Canada to Midway

Keep the following information in mind while searching for Canada to Midway flight deals. Data was last updated September 15, 2025.

Round-trip from

$172
(Booking.com)

One-way from

$121
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$254

Good round-trip deal

$188 or less

Good one-way deal

$153 or less
From Canada to Chicago Midway
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One-way flight from Canada to Chicago Midway
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Highest demand for flights based on searches. 8% potential increase in price ($22 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 September 2025
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Price to beat on a round-trip flight from Canada to Chicago Midway.
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Price to beat on a one-way flight from Canada to Chicago Midway.
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Find flight deals from Canada to Midway

Cheapest flights from Canada to Midway
Explore the most affordable flight options available from Canada to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Booking.com deal was found by Cheapflights users on 9/14. 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.
Fri 10/311:00 amYQB - MDW
1 stop6h 24mPorter Airlines
Tue 10/79:35 amMDW - YQB
1 stop5h 20mPorter Airlines
Deal found 9/14$172
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/2911:00 pmYVR - MDW
1 stop17h 39mMultiple Airlines
Wed 11/52:06 pmMDW - YVR
1 stop23h 06mMultiple Airlines
Deal found 9/14$200
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/208:30 pmYVR - MDW
2 stops15h 08mMultiple Airlines
Wed 10/228:05 amMDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 9/14$202
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/29:30 amYVR - MDW
1 stop12h 11mMultiple Airlines
Mon 10/66:20 amMDW - YVR
1 stop16h 28mMultiple Airlines
Deal found 9/13$204
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/49:30 amYVR - MDW
1 stop12h 11mMultiple Airlines
Tue 10/78:05 amMDW - YVR
1 stop14h 43mMultiple Airlines
Deal found 9/13$206
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/179:00 amYWG - MDW
1 stop14h 46mMultiple Airlines
Wed 10/292:06 pmMDW - YWG
2 stops34h 35mMultiple Airlines
Deal found 9/14$213
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/1711:00 amYQB - MDW
1 stop6h 24mPorter Airlines
Sun 10/199:35 amMDW - YQB
1 stop5h 20mPorter Airlines
Deal found 9/14$216
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:00 pmYWG - MDW
2 stops21h 39mMultiple Airlines
Thu 11/61:37 pmMDW - YWG
1 stop25h 30mMultiple Airlines
Deal found 9/15$218
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 11/38:35 pmYEG - MDW
2 stops14h 03mMultiple Airlines
Sat 11/81:37 pmMDW - YEG
1 stop23h 34mMultiple Airlines
Deal found 9/12$218
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 11/16:00 amYEG - MDW
2 stops11h 39mMultiple Airlines
Sat 11/81:37 pmMDW - YEG
1 stop23h 34mMultiple Airlines
Deal found 9/12$220
This Booking.com deal was found by Cheapflights users on 9/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/229:15 amYHZ - MDW
2 stops9h 09mPorter Airlines
Wed 10/2911:00 amMDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 9/15$220
This Trip.com deal was found by Cheapflights users on 9/15. 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.
Sun 11/98:30 amYHZ - MDW
1 stop8h 50mPorter Airlines
Thu 11/2011:00 amMDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 9/15$229

Cheapflights Fare Finder

 
Customize your flight search to find flights from Canada to Midway 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 September 15, 2025.
Use the filters below to find and compare flights from Canada to Chicago Midway Airport that are best for you.

Fly from

Canada

Fly to

Midway

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 10/2

9:30 am-11:41 pm

1 stop12h 11m

Chicago Midway

Mon 10/6

5:33 pm-1:36 pm

2 stops22h 03m

$205

Québec CityChicago

YQB - MDW

YQBMDW

Québec City

Fri 10/17

11:00 am-4:24 pm

1 stop6h 24m

Chicago Midway

Sun 10/19

9:35 am-3:55 pm

1 stop5h 20m

$216

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/30

9:00 pm-6:39 pm

2 stops21h 39m

Chicago Midway

Thu 11/6

1:37 pm-3:07 pm

1 stop25h 30m

$218

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Mon 11/3

8:35 pm-11:38 am

2 stops14h 03m

Chicago Midway

Sat 11/8

1:37 pm-12:11 pm

1 stop23h 34m

$218

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Fri 10/31

12:45 am-6:39 pm

1 stop16h 54m

Chicago Midway

Sat 11/8

1:37 pm-12:11 pm

1 stop23h 34m

$222

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 10/14

7:30 pm-11:25 pm

1 stop4h 55m

Chicago Midway

Thu 10/23

9:35 am-12:17 pm

Nonstop1h 42m

$234

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 10/22

9:15 am-4:24 pm

2 stops9h 09m

Chicago Midway

Wed 10/29

11:00 am-8:05 pm

1 stop7h 05m

$235

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 10/16

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

Sun 10/19

5:20 pm-10:15 pm

1 stop3h 55m

$236

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 10/15

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Sun 10/19

5:20 pm-10:15 pm

1 stop3h 55m

$238

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/17

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Mon 10/20

5:20 pm-10:15 pm

1 stop3h 55m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 60 results
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Best time to book a flight from Canada to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Canada 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 Canada to Chicago Midway Airport

What is the cheapest month to book a flight from Canada to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of $160). Flying from Canada to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 CA to MDW?

Find hourly flight availability from Canada to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Canada to Chicago Midway Airport as you normally would.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated September 15, 2025.
Read through reviews of airlines operating flights from Canada to Chicago Midway Airport, 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
363 reviews

Crew

8.6

Comfort

7.9

Overall

7.9

Entertainment

7.0

Boarding

8.1

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews

Crew

8.6

Comfort

7.9

Overall

7.9

Entertainment

7.0

Boarding

8.1

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

Related info for your journey

Find useful and relevant information for your journey from Canada to Midway. 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 Canada to Chicago Midway Airport?

    Airlines like Porter Airlines, Delta, and WestJet fly from Canada to Chicago Midway Airport in about 5h 10m. The time it takes to get you to your destination can typically vary by up to 4h 48m. The distance from Canada to Chicago Midway Airport is about 432 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 Canada to Chicago Midway Airport one-way?

    The cheapest airlines for a one-way flight from Canada to Chicago Midway Airport are Porter Airlines ($136), Delta ($138), and WestJet ($159).

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

    The most popular route from Canada to Chicago Midway Airport is Toronto Island - Chicago Midway. You may also consider Toronto Pearson Intl - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago Midway.

  • Can I find deals for flights from Canada to Midway that include hotel bookings?

    Yes. In addition to deals on Canada to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Canada to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Canada to Midway.

  • Can I find deals for business class flights from Canada to Midway?

    Yes. Cheapflights offers flight deals from Canada to Midway 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 Canada to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of $160). Flying from Canada to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top airline flying from Canada to Midway

Discover the top airline that operate flights from Canada to Midway. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$289FlexibilityNo cancel feeOn-time52%

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