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Midway

$126+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
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 May 10, 2026.

This Kissandfly.com deal was found by Cheapflights users on 5/7. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:55 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/3110:30 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 5/7$204
This FlightHub deal was found by Cheapflights users on 5/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/128:45 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 6/1610:15 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 5/9$207
This FlightHub deal was found by Cheapflights users on 5/6. 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.
Thu 5/288:55 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 5/3010:30 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 5/6$208
This FlightHub deal was found by Cheapflights users on 5/5. 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.
Thu 5/288:55 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 6/110:15 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 5/5$209
This Trip.com deal was found by Cheapflights users on 5/7. 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.
Thu 6/48:45 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 6/1110:15 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 5/7$211
This Cheapflightsfares deal was found by Cheapflights users on 5/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/221:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/2410:30 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 5/8$212
This Cheapflightsfares deal was found by Cheapflights users on 5/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/241:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 5/2610:30 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 5/8$213
This Super.com deal was found by Cheapflights users on 5/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/221:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 5/2510:30 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 5/8$214
This Trip.com deal was found by Cheapflights users on 5/5. 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 5/291:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/3110:30 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 5/5$215
This Delta deal was found by Cheapflights users on 5/6. 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.
Thu 5/284:04 pm
YYZ
-
MDW
1 stop3h 29m
Delta
Sun 5/319:22 am
MDW
-
YYZ
1 stop3h 08m
Delta
Deal found 5/6$259
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 6/1110:35 am
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Sun 6/1410:15 am
MDW
-
YUL
1 stop6h 00m
Porter Airlines
Deal found 5/7$268
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 6/46:30 am
YUL
-
MDW
1 stop4h 05m
Porter Airlines
Tue 6/910:15 am
MDW
-
YUL
1 stop6h 00m
Porter Airlines
Deal found 5/7$269

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 May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$203
(Kissandfly.com)

One-way from

$126
(Mytrip)

Popular in

May

Cheapest in

July

Average price

$279

Good round-trip deal

$201 or less

Good one-way deal

$156 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. 4% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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.
Search Deals

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 May 10, 2026.
Use the filters below to find and compare flights from Canada to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 5/28

8:55 am-9:45 am

Nonstop1h 50m

Chicago Midway

Fri 5/29

10:30 am-1:10 pm

Nonstop1h 40m

$207

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 6/25

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Thu 7/2

3:20 pm-6:00 pm

Nonstop1h 40m

$209

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 6/12

8:45 am-9:35 am

Nonstop1h 50m

Chicago Midway

Sun 6/14

10:15 am-12:55 pm

Nonstop1h 40m

$211

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 6/8

8:45 am-9:35 am

Nonstop1h 50m

Chicago Midway

Mon 6/15

10:15 am-12:55 pm

Nonstop1h 40m

$221

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 6/15

8:45 am-9:35 am

Nonstop1h 50m

Chicago Midway

Fri 6/19

3:20 pm-6:00 pm

Nonstop1h 40m

$223

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 6/1

8:45 am-9:35 am

Nonstop1h 50m

Chicago Midway

Sun 6/7

10:15 am-12:55 pm

Nonstop1h 40m

$225

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 7/14

8:50 am-9:40 am

Nonstop1h 50m

Chicago Midway

Tue 8/11

10:25 am-1:05 pm

Nonstop1h 40m

$231

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 6/15

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Tue 6/16

10:15 am-12:55 pm

Nonstop1h 40m

$233

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 5/27

8:55 am-9:45 am

Nonstop1h 50m

Chicago Midway

Thu 5/28

10:30 am-1:10 pm

Nonstop1h 40m

$233

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 7/25

8:50 am-9:40 am

Nonstop1h 50m

Chicago Midway

Wed 7/29

3:20 pm-6:00 pm

Nonstop1h 40m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/9

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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 $80). Flying from Canada to Chicago Midway Airport in December is currently the most expensive (average of $194). 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 May 10, 2026.

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 in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 29% on airfare.

How often are flights from Canada to Chicago delayed?

About 16% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 110 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?

Thursday 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 15% 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 May 10, 2026.
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
437 reviews

Entertainment

7.0

Comfort

8.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
437 reviews
Porter Airlines
8.0
Very good
437 reviews

Entertainment

7.0

Comfort

8.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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 1h 39m. 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 $80). Flying from Canada to Chicago Midway Airport in December is currently the most expensive (average of $194). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Canada to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$80Average$297FlexibilityNo cancel feeOn-time52%

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