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$124+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$199
(Trip.com)

One-way from

$124
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$279

Good round-trip deal

$170 or less

Good one-way deal

$119 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
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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. 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 ($3 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 31, 2025.

This Trip.com deal was found by Cheapflights users on 3/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/239:30 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 4/3011:15 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 3/31$199
This Delta deal was found by Cheapflights users on 3/31. 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.
Sun 5/116:30 amYYC - MDW
1 stop5h 45mDelta
Tue 5/131:55 pmMDW - YYC
1 stop7h 45mDelta
Deal found 3/31$218
This FlightHub deal was found by Cheapflights users on 3/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2110:45 amYUL - MDW
1 stop6h 55mPorter Airlines
Tue 4/295:35 pmMDW - YUL
1 stop4h 12mPorter Airlines
Deal found 3/29$240
This Gotogate deal was found by Cheapflights users on 3/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/144:05 pmYTZ - MDW
Nonstop1h 49mAir Transat
Wed 5/219:40 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 3/30$243
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/211:00 pmYVR - MDW
1 stop8h 33mMultiple Airlines
Tue 5/69:34 amMDW - YVR
1 stop13h 18mMultiple Airlines
Deal found 3/30$246
This Trip.com deal was found by Cheapflights users on 3/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/13:35 pmYTZ - MDW
Nonstop1h 49mMultiple Airlines
Sun 5/49:40 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 3/30$248
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1012:30 amYYC - MDW
1 stop12h 04mMultiple Airlines
Tue 5/139:34 amMDW - YYC
1 stop11h 31mMultiple Airlines
Deal found 3/31$252
This Delta deal was found by Cheapflights users on 3/31. 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.
Thu 4/246:00 amYYZ - MDW
1 stop3h 40mDelta
Sun 4/279:20 amMDW - YYZ
1 stop6h 58mDelta
Deal found 3/31$259
This Delta deal was found by Cheapflights users on 3/29. 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.
Sun 4/206:10 amYUL - MDW
1 stop9h 12mDelta
Tue 4/296:04 amMDW - YUL
1 stop9h 48mDelta
Deal found 3/29$268
This Trip.com deal was found by Cheapflights users on 3/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/19:35 amYEG - MDW
1 stop13h 04mMultiple Airlines
Thu 5/88:30 amMDW - YEG
1 stop12h 18mMultiple Airlines
Deal found 3/30$274
This FlightHub deal was found by Cheapflights users on 3/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/11:27 pmYYZ - MDW
1 stop9h 55mWestJet
Sat 5/31:16 pmMDW - YYZ
1 stop21h 43mWestJet
Deal found 3/30$293
This Delta deal was found by Cheapflights users on 3/31. 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.
Sat 5/319:25 amYEG - MDW
1 stop7h 22mDelta
Mon 6/29:20 amMDW - YEG
1 stop7h 38mDelta
Deal found 3/31$300

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 March 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

Wed 4/23

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Wed 4/30

11:15 am-1:57 pm

Nonstop1h 42m

$199

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 5/11

6:30 am-1:15 pm

1 stop5h 45m

Chicago Midway

Tue 5/13

1:55 pm-8:40 pm

1 stop7h 45m

$218

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 4/21

10:45 am-4:40 pm

1 stop6h 55m

Chicago Midway

Tue 4/29

5:35 pm-10:47 pm

1 stop4h 12m

$240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 5/14

4:05 pm-4:54 pm

Nonstop1h 49m

Chicago Midway

Wed 5/21

9:40 am-12:22 pm

Nonstop1h 42m

$243

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 5/2

11:00 pm-9:33 am

1 stop8h 33m

Chicago Midway

Tue 5/6

9:34 am-8:52 pm

1 stop13h 18m

$246

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 5/1

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Sun 5/4

9:40 am-12:22 pm

Nonstop1h 42m

$248

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 5/10

12:30 am-1:34 pm

1 stop12h 04m

Chicago Midway

Tue 5/13

9:34 am-8:05 pm

1 stop11h 31m

$252

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 4/24

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Sun 4/27

9:20 am-5:18 pm

1 stop6h 58m

$259

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 4/20

6:10 am-2:22 pm

1 stop9h 12m

Chicago Midway

Tue 4/29

6:04 am-4:52 pm

1 stop9h 48m

$268

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Thu 5/1

9:35 am-11:39 pm

1 stop13h 04m

Chicago Midway

Thu 5/8

8:30 am-7:48 pm

1 stop12h 18m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

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 March 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.

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 March 31, 2025.
Peruse reviews from past customers who have flown with Delta, Porter Airlines and Air Transat from Canada to Chicago to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,899 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Porter Airlines
7.9
Good
277 reviews
Delta
8.0
Very good
7,899 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Transat
7.8
Good
381 reviews
Delta
8.0
Very good
7,899 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,789 reviews
Delta
8.0
Very good
7,899 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 ($124), Delta ($135), and Air Transat ($147).

  • 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 Canada?

Book flights to Canada if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$170Average$339FlexibilityNo cancel feeOn-time52%
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