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Midway

$103+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$149
(SmartFares)

One-way from

$103
(SmartFares)

Popular in

December

Cheapest in

June

Average price

$270

Good round-trip deal

$170 or less

Good one-way deal

$101 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. 7% potential increase in price ($21 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 July 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 julio 31, 2025.

This SmartFares deal was found by Cheapflights users on 7/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/163:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
lun. 9/225:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/29$149
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
lun. 9/19:00 amYTZ - MDW
Nonstop1h 50mAir Transat
mié. 9/39:35 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 7/29$166
This Mytrip deal was found by Cheapflights users on 7/29. 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.
jue. 9/257:50 amYTZ - MDW
Nonstop1h 49mMultiple Airlines
lun. 9/295:20 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 7/29$196
This Flightnetwork deal was found by Cheapflights users on 7/29. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/310:45 amYUL - MDW
1 stop6h 39mPorter Airlines
dom. 10/55:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Deal found 7/29$198
This Delta deal was found by Cheapflights users on 7/29. 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.
sáb. 9/1312:14 pmYYZ - MDW
1 stop7h 21mDelta
sáb. 9/201:43 pmMDW - YYZ
1 stop8h 37mDelta
Deal found 7/29$212
This Delta deal was found by Cheapflights users on 7/30. 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.
mié. 9/36:00 amYUL - MDW
1 stop3h 35mDelta
sáb. 9/66:00 amMDW - YUL
1 stop6h 38mDelta
Deal found 7/30$215
This Delta deal was found by Cheapflights users on 7/31. 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.
mié. 9/109:25 amYEG - MDW
1 stop7h 12mDelta
sáb. 9/139:20 amMDW - YEG
1 stop7h 39mDelta
Deal found 7/31$243
This Delta deal was found by Cheapflights users on 7/30. 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.
mié. 9/106:40 amYYC - MDW
1 stop5h 23mDelta
sáb. 9/139:20 amMDW - YYC
2 stops14h 42mDelta
Deal found 7/30$244
This FlightHub deal was found by Cheapflights users on 7/31. 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.
vie. 10/1711:52 amYYZ - MDW
1 stop11h 22mWestJet
mar. 10/2112:48 pmMDW - YYZ
1 stop8h 07mWestJet
Deal found 7/31$268
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
vie. 10/39:30 amYVR - MDW
1 stop11h 50mMultiple Airlines
mié. 10/88:00 amMDW - YVR
1 stop14h 48mMultiple Airlines
Deal found 7/29$290
This Delta deal was found by Cheapflights users on 7/29. 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.
vie. 8/296:15 amYVR - MDW
1 stop9h 22mDelta
mié. 9/31:43 pmMDW - YVR
2 stops11h 15mDelta
Deal found 7/29$308
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
jue. 8/2112:35 pmYOW - MDW
1 stop4h 49mPorter Airlines
mar. 8/269:40 amMDW - YOW
1 stop6h 23mPorter Airlines
Deal found 7/28$324

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 julio 31, 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

mar. 9/16

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

lun. 9/22

5:20 pm-8:02 pm

Nonstop1h 42m

$149

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

lun. 9/1

9:00 am-9:50 am

Nonstop1h 50m

Chicago Midway

mié. 9/3

9:35 am-12:17 pm

Nonstop1h 42m

$166

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 9/25

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

lun. 9/29

5:20 pm-8:02 pm

Nonstop1h 42m

$196

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

vie. 10/3

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

dom. 10/5

5:20 pm-10:15 pm

1 stop3h 55m

$198

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

sáb. 9/13

12:14 pm-6:35 pm

1 stop7h 21m

Chicago Midway

sáb. 9/20

6:15 pm-10:56 pm

1 stop3h 41m

$212

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

mié. 9/3

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

sáb. 9/6

6:00 am-1:38 pm

1 stop6h 38m

$215

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

mié. 9/10

9:25 am-5:37 pm

1 stop7h 12m

Chicago Midway

sáb. 9/13

9:20 am-3:59 pm

1 stop7h 39m

$243

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

mié. 9/10

6:40 am-1:03 pm

1 stop5h 23m

Chicago Midway

sáb. 9/13

9:20 am-11:02 pm

2 stops14h 42m

$244

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

vie. 10/17

11:52 am-10:14 pm

1 stop11h 22m

Chicago Midway

mar. 10/21

12:48 pm-9:55 pm

1 stop8h 07m

$268

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

vie. 10/3

9:30 am-11:20 pm

1 stop11h 50m

Chicago Midway

mié. 10/8

8:00 am-8:48 pm

1 stop14h 48m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 julio 31, 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 julio 31, 2025.
Read through reviews of airlines operating flights from Canada to Chicago Midway Airport, such as Porter Airlines, Delta, and Air Transat. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,981 reviews
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Transat
7.7
Good
424 reviews
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,978 reviews
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

  • 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 ($103), Air Transat ($106), and Delta ($134).

  • 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
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$291FlexibilityNo cancel feeOn-time52%

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