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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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
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Cheap flight deals from Midway to Canada

Keep the following information in mind while searching for Midway to Canada flight deals. Data was last updated March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$220
(Trip.com)

One-way from

$100
(Delta)

Popular in

March

Cheapest in

April

Average price

$400

Good round-trip deal

$224 or less

Good one-way deal

$139 or less
Provider with most accurate pricing for Chicago (CHI)-Toronto (YTO) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Toronto (YTO) flights.
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From Chicago Midway to Canada
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One-way flight from Chicago Midway to Canada
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Highest demand for flights based on searches. 5% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 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 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 March 28, 2025.

This Trip.com deal was found by Cheapflights users on 3/27. 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 4/2411:15 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 5/17:55 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 3/27$220
This Flightnetwork deal was found by Cheapflights users on 3/27. 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.
Fri 4/1811:15 amMDW - YUL
1 stop4h 32mPorter Airlines
Mon 4/216:50 amYUL - MDW
1 stop4h 30mPorter Airlines
Deal found 3/27$233
This Flightnetwork deal was found by Cheapflights users on 3/27. 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.
Sat 5/39:40 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Sat 5/107:55 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 3/27$234
This Delta deal was found by Cheapflights users on 3/27. 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.
Tue 5/131:55 pmMDW - YYC
1 stop7h 45mDelta
Sun 5/256:30 amYYC - MDW
1 stop5h 45mDelta
Deal found 3/27$250
This Delta deal was found by Cheapflights users on 3/26. 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.
Tue 5/139:20 amMDW - YYZ
1 stop8h 11mDelta
Wed 6/113:31 pmYYZ - MDW
1 stop4h 14mDelta
Deal found 3/26$255
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 4/2511:15 amMDW - YTZ
Nonstop1h 42mAir Transat
Mon 4/289:30 amYTZ - MDW
Nonstop1h 50mAir Transat
Deal found 3/27$263
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 5/18:03 pmMDW - YYC
1 stop19h 42mMultiple Airlines
Sun 5/412:30 amYYC - MDW
1 stop12h 04mMultiple Airlines
Deal found 3/27$270
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 5/69:34 amMDW - YVR
1 stop13h 18mMultiple Airlines
Wed 5/711:00 pmYVR - MDW
1 stop22h 39mMultiple Airlines
Deal found 3/27$285
This Gotogate deal was found by Cheapflights users on 3/27. 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.
Sun 6/159:40 amMDW - YUL
1 stop6h 40mMultiple Airlines
Thu 6/191:10 pmYUL - MDW
1 stop4h 14mMultiple Airlines
Deal found 3/27$299
This Delta deal was found by Cheapflights users on 3/27. 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.
Tue 8/129:20 amMDW - YEG
1 stop7h 38mDelta
Tue 8/269:25 amYEG - MDW
1 stop7h 38mDelta
Deal found 3/27$310
This Kiwi.com deal was found by Cheapflights users on 3/26. 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 6/27:05 amMDW - YWG
1 stop9h 23mMultiple Airlines
Fri 6/69:00 amYWG - MDW
1 stop14h 22mMultiple Airlines
Deal found 3/26$326
This Delta deal was found by Cheapflights users on 3/26. 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 5/116:25 pmMDW - YUL
1 stop3h 51mDelta
Sun 5/186:00 amYUL - MDW
1 stop3h 40mDelta
Deal found 3/26$329

Cheapflights Fare Finder

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 March 28, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Canada that are best for you.

Fly from

Midway

Fly to

Canada

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 4/24

11:15 am-1:57 pm

Nonstop1h 42m

Toronto Island

Thu 5/1

7:55 am-8:45 am

Nonstop1h 50m

$220

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 4/18

11:15 am-4:47 pm

1 stop4h 32m

Montreal Pierre Elliott Trudeau Intl

Mon 4/21

6:50 am-10:20 am

1 stop4h 30m

$233

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 5/3

9:40 am-12:22 pm

Nonstop1h 42m

Toronto Island

Sat 5/10

7:55 am-8:45 am

Nonstop1h 50m

$234

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 5/13

1:55 pm-8:40 pm

1 stop7h 45m

Calgary

Sun 5/25

6:30 am-1:15 pm

1 stop5h 45m

$250

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 5/13

9:20 am-6:31 pm

1 stop8h 11m

Toronto Pearson Intl

Wed 6/11

3:31 pm-6:45 pm

1 stop4h 14m

$255

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 4/25

11:15 am-1:57 pm

Nonstop1h 42m

Toronto Island

Mon 4/28

9:30 am-10:20 am

Nonstop1h 50m

$263

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 5/1

8:03 pm-2:45 pm

1 stop19h 42m

Calgary

Sun 5/4

12:30 am-1:34 pm

1 stop12h 04m

$270

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Tue 5/6

9:34 am-8:52 pm

1 stop13h 18m

Vancouver Intl

Wed 5/7

11:00 pm-11:39 pm

1 stop22h 39m

$285

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sun 6/15

9:40 am-5:20 pm

1 stop6h 40m

Montreal Pierre Elliott Trudeau Intl

Thu 6/19

1:10 pm-4:24 pm

1 stop4h 14m

$299

ChicagoEdmonton

MDW - YEG

MDWYEG

Chicago Midway

Tue 8/12

9:20 am-3:58 pm

1 stop7h 38m

Edmonton

Tue 8/26

9:25 am-6:03 pm

1 stop7h 38m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Canada

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 March 28, 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 March 28, 2025.
Read reviews from past customers who have flown Delta, Porter Airlines and Air Transat 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
7,896 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,896 reviews
Delta
8.0
Very good
7,896 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Porter Airlines
7.9
Good
276 reviews
Delta
8.0
Very good
7,896 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

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
7,896 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
WestJet
7.2
Good
2,785 reviews
Delta
8.0
Very good
7,896 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

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 $104 and Air Transat from $116 one-way.

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

    Most travelers choose Chicago Midway - Vancouver Intl, Chicago Midway - Toronto Pearson Intl 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$223Average$380FlexibilityNo cancel feeOn-time52%
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