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$131+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$200
(Kiwi.com)

One-way from

$131
(Mytrip)

Popular in

December

Cheapest in

April

Average price

$285

Good round-trip deal

$228 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. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/20. 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 4/23:55 pmYVR - MDW
1 stop11h 28mMultiple Airlines
Tue 4/88:50 pmMDW - YVR
1 stop27h 40mMultiple Airlines
Deal found 2/20$200
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/203:50 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 3/245:35 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/19$204
This Delta deal was found by Cheapflights users on 2/20. 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.
Mon 3/36:35 amYYC - MDW
1 stop10h 08mDelta
Wed 3/51:26 pmMDW - YYC
1 stop8h 27mDelta
Deal found 2/20$220
This Trip.com deal was found by Cheapflights users on 2/18. 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 3/203:50 pmYTZ - MDW
Nonstop1h 50mAir Transat
Thu 3/275:35 pmMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 2/18$223
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 4/189:30 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Sat 4/1912:55 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 2/20$244
This CheapTicketsDeal deal was found by Cheapflights users on 2/20. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/126:30 amYYZ - MDW
1 stop13h 03mWestJet
Sun 4/2010:20 amMDW - YYZ
1 stop24h 14mWestJet
Deal found 2/20$244
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 4/1812:15 pmYYZ - MDW
1 stop7h 05mDelta
Tue 4/223:02 pmMDW - YYZ
1 stop6h 53mDelta
Deal found 2/20$246
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Tue 4/86:40 amYEG - MDW
1 stop8h 01mMultiple Airlines
Tue 4/1510:13 amMDW - YEG
2 stops13h 34mMultiple Airlines
Deal found 2/19$249
This Trip.com deal was found by Cheapflights users on 2/20. 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 4/66:50 amYUL - MDW
1 stop4h 30mPorter Airlines
Sun 4/1311:15 amMDW - YUL
1 stop4h 37mPorter Airlines
Deal found 2/20$259
This Booking.com deal was found by Cheapflights users on 2/20. 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 4/28:25 amYHZ - MDW
2 stops10h 15mPorter Airlines
Sat 4/1212:55 pmMDW - YHZ
1 stop5h 50mPorter Airlines
Deal found 2/20$269
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 4/2512:50 pmYUL - MDW
1 stop6h 30mDelta
Tue 4/2912:48 pmMDW - YUL
1 stop10h 11mDelta
Deal found 2/20$276
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/153:45 pmYYC - MDW
1 stop12h 45mMultiple Airlines
Wed 3/199:25 amMDW - YYC
1 stop8h 37mMultiple Airlines
Deal found 2/19$291

Find flights from Canada to Midway within your budget

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 February 20, 2025.

Fly from

Canada

Fly to

Midway

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 4/2

3:55 pm-5:23 am

1 stop11h 28m

Chicago Midway

Tue 4/8

8:50 pm-10:30 pm

1 stop27h 40m

$200

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 3/20

3:50 pm-4:40 pm

Nonstop1h 50m

Chicago Midway

Mon 3/24

5:35 pm-8:17 pm

Nonstop1h 42m

$204

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 3/3

6:35 am-5:43 pm

1 stop10h 08m

Chicago Midway

Wed 3/5

1:26 pm-8:53 pm

1 stop8h 27m

$220

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 3/17

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Thu 3/20

5:35 pm-8:17 pm

Nonstop1h 42m

$229

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/12

6:30 am-6:33 pm

1 stop13h 03m

Chicago Midway

Mon 4/21

1:16 pm-11:34 am

1 stop21h 18m

$244

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 4/18

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Sat 4/19

12:55 pm-3:37 pm

Nonstop1h 42m

$244

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 3/20

10:20 am-12:36 pm

1 stop3h 16m

Chicago Midway

Mon 3/24

2:55 pm-10:38 pm

1 stop6h 43m

$247

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Tue 4/8

6:40 am-3:41 pm

1 stop8h 01m

Chicago Midway

Tue 4/15

10:13 am-10:47 pm

2 stops13h 34m

$249

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 4/6

6:50 am-10:20 am

1 stop4h 30m

Chicago Midway

Sun 4/13

11:15 am-4:52 pm

1 stop4h 37m

$259

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 4/2

8:25 am-4:40 pm

2 stops10h 15m

Chicago Midway

Sat 4/12

12:55 pm-8:45 pm

1 stop5h 50m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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.

Travel insights for flights from Canada to Midway

Get recent, data-driven insights about flights from Canada to Midway including ideal travel times, pricing trends, and more.

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 February 20, 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 February 20, 2025.
Peruse reviews from past customers who have flown with Delta, Porter Airlines and KLM 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
8,220 reviews

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

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
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

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
276 reviews
Delta
8.0
Very good
8,220 reviews

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

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

KLM
7.8
Good
1,333 reviews
Delta
8.0
Very good
8,220 reviews

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

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
380 reviews
Delta
8.0
Very good
8,220 reviews

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

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
2,801 reviews
Delta
8.0
Very good
8,220 reviews

Comfort

8.0

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

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 ($131), Delta ($136), and Air Transat ($137).

  • 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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Nashville to O'Hare Intl flights

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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$209Average$340FlexibilityNo cancel feeOn-time52%
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