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Midway

$116+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This FlightHub deal was found by Cheapflights users on 12/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 2/311:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$270
This FlightHub deal was found by Cheapflights users on 12/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 2/311:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$291
This FlightHub deal was found by Cheapflights users on 12/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Mon 2/2311:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 12/16$302
This FlightHub deal was found by Cheapflights users on 12/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Sat 1/34:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Deal found 12/16$334
This Trip.com deal was found by Cheapflights users on 12/15. 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.
Sat 12/276:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Fri 1/24:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Deal found 12/15$345
This Super.com deal was found by Cheapflights users on 12/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/292:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 1/611:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/16$347
This oojo deal was found by Cheapflights users on 12/15. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 2/211:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$355
This Mytrip deal was found by Cheapflights users on 12/16. 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.
Mon 12/299:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 1/2111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/16$362
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/3112:09 pmYYZ - MDW
1 stop6h 17mWestJet
Fri 1/26:08 pmMDW - YYZ
1 stop13h 50mWestJet
Deal found 12/17$365
This Trip.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 1/14:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/16$366
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/3112:09 pmYYZ - MDW
1 stop6h 17mWestJet
Mon 1/56:14 pmMDW - YYZ
1 stop3h 27mWestJet
Deal found 12/16$366
This Trip.com deal was found by Cheapflights users on 12/16. 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.
Sun 12/289:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 1/1012:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/16$368

Find flight deals from Canada to Midway

Keep the following information in mind while searching for Canada to Midway flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$183
(Trip.com)

One-way from

$116
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$321

Good round-trip deal

$210 or less

Good one-way deal

$117 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
Search Deals
From Canada to Chicago Midway
Search Deals
One-way flight from Canada to Chicago Midway
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Canada to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Canada to Chicago Midway.
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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 December 18, 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

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 1/25

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Mon 1/26

11:00 am-1:42 pm

Nonstop1h 42m

$186

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 2/9

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Tue 2/10

11:00 am-1:42 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/16

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Fri 1/23

11:05 am-1:47 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 2/20

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Mon 2/23

11:00 am-1:42 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 1/24

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Thu 1/29

11:00 am-1:42 pm

Nonstop1h 42m

$188

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 2/19

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Mon 2/23

11:00 am-5:45 pm

1 stop5h 45m

$196

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 2/15

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Sun 2/15

4:15 pm-10:45 pm

1 stop5h 30m

$197

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 2/13

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Fri 2/13

4:15 pm-10:45 pm

1 stop5h 30m

$197

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 1/14

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Thu 1/15

11:00 am-1:42 pm

Nonstop1h 42m

$205

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 1/14

12:55 pm-11:47 am

2 stops22h 52m

Chicago Midway

Mon 1/19

12:57 pm-12:43 am

1 stop11h 46m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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, June is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of $83). Flying from Canada to Chicago Midway Airport in December is currently the most expensive (average of $207). 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 December 18, 2025.

One of the essential ways to save on airfare from Canada to Chicago Midway Airport is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 30% on airfare.

How often are flights from Canada to Chicago delayed?

About 14% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 107 minutes.

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

Wednesday 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 Canada to Chicago flights?

Over the last year, Porter Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.

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 December 18, 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
8.0
Very good
399 reviews

Comfort

7.9

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.6

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
8.0
Very good
399 reviews
Porter Airlines
8.0
Very good
399 reviews

Comfort

7.9

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.6

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 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 and Delta fly from Canada to Chicago Midway Airport in about 1h 50m. The time it takes to get you to your destination can typically vary by up to 2h 02m. The distance from Canada to Chicago Midway Airport 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 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, June is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of $83). Flying from Canada to Chicago Midway Airport in December is currently the most expensive (average of $207). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$279FlexibilityNo cancel feeOn-time52%

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