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Midway

$133+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
dic. 23 — dic. 301
lun. 12/23
lun. 12/30
1 adult, Economy
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Cheap flight deals from Canada to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Canada (CA0) to Midway (MDW). 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 diciembre 18, 2024.

Round-trip from

$217
(Delta)

One-way from

$133
(Kiwi.com)
From Canada to Chicago Midway
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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 diciembre 18, 2024.

This Trip.com deal was found by Cheapflights users on 12/17. 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.
lun. 12/303:50 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
lun. 1/131:05 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/17$287
This oojo deal was found by Cheapflights users on 12/17. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/317:00 amYOW - MDW
1 stop4h 20mPorter Airlines
vie. 1/35:35 pmMDW - YOW
1 stop3h 51mPorter Airlines
Deal found 12/17$310
This deal was found by Cheapflights users on 12/16. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/316:50 amYUL - MDW
1 stop4h 30mPorter Airlines
mié. 1/81:05 pmMDW - YUL
1 stop3h 55mPorter Airlines
Deal found 12/16$326
This Gotogate deal was found by Cheapflights users on 12/18. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/289:40 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
jue. 1/25:35 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 12/18$402
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
mar. 12/317:10 amYYZ - MDW
1 stop11h 44mMultiple Airlines
mié. 1/810:57 amMDW - YYZ
1 stop5h 03mMultiple Airlines
Deal found 12/17$416
This Trip.com deal was found by Cheapflights users on 12/17. 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.
mié. 12/256:30 amYYZ - MDW
1 stop5h 38mWestJet
lun. 2/31:26 pmMDW - YYZ
1 stop8h 41mWestJet
Deal found 12/17$453
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/1912:35 pmYYZ - MDW
1 stop6h 09mDelta
dom. 2/22:08 pmMDW - YYZ
1 stop7h 44mDelta
Deal found 12/18$456
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
mar. 12/3112:45 amYEG - MDW
1 stop11h 39mMultiple Airlines
mar. 1/75:24 pmMDW - YEG
2 stops24h 26mMultiple Airlines
Deal found 12/17$479
This Mytrip deal was found by Cheapflights users on 12/16. 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.
lun. 12/305:00 amYWG - MDW
1 stop11h 40mPorter Airlines
dom. 2/21:05 pmMDW - YWG
1 stop10h 35mPorter Airlines
Deal found 12/16$517
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
lun. 12/303:55 pmYVR - MDW
1 stop11h 38mMultiple Airlines
lun. 1/610:04 pmMDW - YVR
2 stops19h 39mMultiple Airlines
Deal found 12/17$558
This WestJet deal was found by Cheapflights users on 12/17. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3112:05 amYEG - MDW
2 stops15h 05mWestJet
mar. 1/72:08 pmMDW - YEG
2 stops11h 26mWestJet
Deal found 12/17$560
This Mytrip deal was found by Cheapflights users on 12/16. 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.
lun. 12/307:00 pmYWG - MDW
1 stop15h 20mMultiple Airlines
dom. 2/21:26 pmMDW - YWG
2 stops21h 19mMultiple Airlines
Deal found 12/16$563

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 diciembre 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

mié. 1/15

6:35 am-5:47 pm

1 stop10h 12m

Chicago Midway

mié. 1/22

1:26 pm-8:53 pm

1 stop8h 27m

$217

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 1/9

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

dom. 1/12

1:05 pm-3:47 pm

Nonstop1h 42m

$234

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

vie. 2/14

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

lun. 2/17

1:05 pm-3:47 pm

Nonstop1h 42m

$236

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

mar. 1/14

12:45 am-5:57 pm

1 stop16h 12m

Chicago Midway

lun. 1/20

6:15 am-10:50 pm

2 stops17h 35m

$244

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

mar. 1/7

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

lun. 2/3

6:28 pm-10:49 pm

1 stop3h 21m

$246

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

dom. 1/12

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

vie. 1/17

5:30 am-4:48 pm

2 stops10h 18m

$250

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

jue. 1/9

6:30 am-12:10 pm

2 stops7h 40m

Chicago Midway

mié. 1/15

1:05 pm-10:25 pm

2 stops7h 20m

$260

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

jue. 1/9

12:30 am-11:51 am

1 stop10h 21m

Chicago Midway

lun. 1/13

7:15 am-10:55 pm

2 stops16h 40m

$264

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

jue. 1/9

12:20 pm-10:12 am

1 stop22h 52m

Chicago Midway

dom. 1/12

10:19 am-11:11 pm

1 stop11h 52m

$274

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

vie. 1/31

11:00 pm-11:29 pm

1 stop22h 29m

Chicago Midway

vie. 2/7

6:40 am-11:14 am

1 stop30h 34m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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 October is currently the most expensive (average of $232). 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 diciembre 18, 2024.

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 diciembre 18, 2024.
Peruse reviews from past customers who have flown with Air Transat, WestJet and Delta 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
8,604 reviews

Crew

8.6

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

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

Delta
8.0
Very good
8,604 reviews
Delta
8.0
Very good
8,604 reviews

Crew

8.6

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

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

Porter Airlines
7.9
Good
283 reviews
Delta
8.0
Very good
8,604 reviews

Crew

8.6

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

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

KLM
7.8
Good
1,349 reviews
Delta
8.0
Very good
8,604 reviews

Crew

8.6

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

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

Air Transat
7.8
Good
389 reviews
Delta
8.0
Very good
8,604 reviews

Crew

8.6

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

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

WestJet
7.3
Good
2,818 reviews
Delta
8.0
Very good
8,604 reviews

Crew

8.6

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

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 Delta ($134), Porter Airlines ($140), and WestJet ($166).

  • 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 October is currently the most expensive (average of $232). 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.

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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 diciembre 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$206Average$336FlexibilityNo cancel feeOn-time52%
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