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$100+ Cheap flights from Midway (MDW) to Canada

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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Midway to Canada

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Canada (CA0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$197
(flugladen.de)

One-way from

$100
(Delta)

Good round-trip deal

$293 or less

Good one-way deal

$191 or less
From Chicago Midway to Canada
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One-way flight from Chicago Midway to Canada
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Price to beat on a round-trip flight from Chicago Midway to Canada.
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Price to beat on a one-way flight from Chicago Midway to Canada.
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Find flight deals from Midway to Canada

Cheapest flights from Midway to Canada
Explore the most affordable flight options available from Midway to Canada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.

This Trip.com deal was found by Cheapflights users on 1/21. 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.
Tue 2/251:05 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 2/2711:20 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 1/21$200
This Mytrip deal was found by Cheapflights users on 1/21. 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.
Thu 2/131:05 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Sun 2/1611:20 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 1/21$218
This Trip.com deal was found by Cheapflights users on 1/20. 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.
Thu 4/311:15 amMDW - YTZ
Nonstop1h 42mAir Transat
Mon 4/73:50 pmYTZ - MDW
Nonstop1h 50mAir Transat
Deal found 1/20$240
This Trip.com deal was found by Cheapflights users on 1/20. 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.
Fri 2/281:05 pmMDW - YUL
1 stop5h 20mPorter Airlines
Sun 3/26:50 amYUL - MDW
1 stop4h 30mPorter Airlines
Deal found 1/20$247
This Delta deal was found by Cheapflights users on 1/20. 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 2/101:26 pmMDW - YYC
1 stop8h 27mDelta
Sun 2/166:35 amYYC - MDW
1 stop10h 08mDelta
Deal found 1/20$250
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 3/47:05 amMDW - YVR
2 stops17h 25mMultiple Airlines
Mon 3/105:30 pmYVR - MDW
1 stop10h 01mMultiple Airlines
Deal found 1/21$261
This Flightnetwork deal was found by Cheapflights users on 1/21. 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.
Thu 2/61:05 pmMDW - YHZ
1 stop5h 40mPorter Airlines
Wed 2/128:35 amYHZ - MDW
1 stop5h 35mPorter Airlines
Deal found 1/21$287
This Flightnetwork deal was found by Cheapflights users on 1/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/611:15 amMDW - YOW
1 stop4h 54mPorter Airlines
Thu 3/137:00 amYOW - MDW
1 stop4h 20mPorter Airlines
Deal found 1/20$294
This Kissandfly.com deal was found by Cheapflights users on 1/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/131:26 pmMDW - YYZ
1 stop8h 41mKLM
Sun 2/166:30 amYYZ - MDW
1 stop5h 17mKLM
Deal found 1/20$300
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Mon 1/2711:33 amMDW - YOW
1 stop7h 44mMultiple Airlines
Mon 2/39:30 amYOW - MDW
1 stop3h 40mMultiple Airlines
Deal found 1/20$310
This Mytrip deal was found by Cheapflights users on 1/21. 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.
Thu 2/271:05 pmMDW - YUL
1 stop10h 34mMultiple Airlines
Sun 3/26:50 amYUL - MDW
1 stop4h 30mMultiple Airlines
Deal found 1/21$320
This Delta deal was found by Cheapflights users on 1/21. 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 3/61:26 pmMDW - YYZ
1 stop8h 41mDelta
Mon 3/106:00 amYYZ - MDW
1 stop7h 36mDelta
Deal found 1/21$322

Find flights from Midway to Canada within your budget

Customize your flight search to find flights from Midway to Canada 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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 2/13

1:05 pm-3:47 pm

Nonstop1h 42m

Toronto Island

Sun 2/16

11:20 am-12:10 pm

Nonstop1h 50m

$197

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 3/6

11:15 am-1:57 pm

Nonstop1h 42m

Toronto Island

Thu 3/13

3:50 pm-4:40 pm

Nonstop1h 50m

$212

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 3/22

12:55 pm-3:37 pm

Nonstop1h 42m

Toronto Island

Wed 3/26

9:30 am-10:20 am

Nonstop1h 50m

$240

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 2/28

1:05 pm-7:25 pm

1 stop5h 20m

Montreal Pierre Elliott Trudeau Intl

Sun 3/2

6:50 am-10:20 am

1 stop4h 30m

$247

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 2/10

1:26 pm-8:53 pm

1 stop8h 27m

Calgary

Sun 2/16

6:35 am-5:43 pm

1 stop10h 08m

$250

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Tue 3/4

7:05 am-10:30 pm

2 stops17h 25m

Vancouver Intl

Mon 3/10

5:30 pm-5:31 am

1 stop10h 01m

$261

ChicagoHalifax

MDW - YHZ

MDWYHZ

Chicago Midway

Thu 2/6

1:05 pm-8:45 pm

1 stop5h 40m

Halifax Intl

Wed 2/12

8:35 am-12:10 pm

1 stop5h 35m

$287

ChicagoOttawa

MDW - YOW

MDWYOW

Chicago Midway

Thu 3/6

11:15 am-5:09 pm

1 stop4h 54m

Ottawa

Thu 3/13

7:00 am-10:20 am

1 stop4h 20m

$294

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 2/13

1:26 pm-11:07 pm

1 stop8h 41m

Toronto Pearson Intl

Sun 2/16

6:30 am-10:47 am

1 stop5h 17m

$300

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 3/6

9:33 am-4:09 pm

1 stop5h 36m

Toronto Pearson Intl

Thu 3/13

2:45 pm-6:18 pm

1 stop4h 33m

$322

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 60 results
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Best time to book a flight from Midway to Canada

Have a flexible travel schedule? Discover the best time to fly to Canada from Midway 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 Midway to Canada

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

What is the cheapest month to book a flight from Chicago Midway Airport to Canada?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Canada (average of $243). Flying from Chicago Midway Airport to Canada in July is currently the most expensive (average of $359). 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 MDW to CA?

Find hourly flight availability from Midway to Canada. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 21, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Canada as you normally would.

Rainfall in Canada by month

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

In terms of precipitation, rainfall in Canada ranges from 2.0 - 3.3 inches per month. June is typically the wettest month, when rainfall can reach 3.3 in. February is typically the driest time to visit Canada when rainfall is around 2.0 in.

Temperature in Canada by month

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

If weather is an important factor for your trip to Canada, 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 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

Reviews of airlines servicing Canada

Get insights into the airlines that provide service to Canada. 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 Canada. Reviews last updated January 21, 2025.
Read reviews from past customers who have flown WestJet, Delta and KLM from Chicago to Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Porter Airlines
7.9
Good
277 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

KLM
7.8
Good
1,341 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Air Transat
7.8
Good
381 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

WestJet
7.2
Good
2,829 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Midway to Canada. 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 Chicago Midway Airport to Canada one-way?

    One-way options have recently been found by users for as low as $100 on Delta. Other airlines that offer cheap prices include Porter Airlines from $111 and KLM from $124 one-way.

  • What are the most popular routes from Chicago Midway Airport to Canada?

    Most travelers choose Chicago Midway - Vancouver Intl, Chicago Midway - Calgary or Chicago Midway - Toronto Island when deciding on the best route from Chicago Midway Airport to Canada.

  • Can I find deals for flights from Midway to Canada that include hotel bookings?

    Yes. In addition to deals on Midway to Canada flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Canada?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Canada.

  • Can I find deals for business class flights from Midway to Canada?

    Yes. Cheapflights offers flight deals from Midway to Canada 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 Chicago Midway Airport to Canada?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Canada (average of $243). Flying from Chicago Midway Airport to Canada in July is currently the most expensive (average of $359). 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

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Alternative routes for Midway to Canada

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Midway to Canada

Discover the top airline that operate flights from Midway to Canada. 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$233Average$396FlexibilityNo cancel feeOn-time52%
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