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Cheap flights from Canada to Chicago Midway Airport from C$ 178

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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
24 Dec — 31 Dec1
1 adult

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 19 December 2024.

Round-trip from

C$ 311

One-way from

C$ 178
Delta
  • Delta
  • 30/1-3/2
  • 2 total stops
  • 13h 38m total
  • Canada to Chicago
Search Deals
7/1
  • 7/1
  • 1 total stop
  • 8h 44m total
  • Canada to Chicago
Search Deals

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 19 December 2024.

Wed 25/123:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 27/11:05 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/12C$ 426
Tue 31/127:00 a.m.YOW - MDW
1 stop4h 20mPorter Airlines
Fri 3/15:35 p.m.MDW - YOW
1 stop3h 51mPorter Airlines
Deal found 17/12C$ 445
Tue 31/126:50 a.m.YUL - MDW
1 stop4h 30mPorter Airlines
Fri 3/15:35 p.m.MDW - YUL
1 stop4h 10mPorter Airlines
Deal found 17/12C$ 472
Sat 28/129:40 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Thu 2/112:05 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 18/12C$ 539
Sat 28/129:40 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Thu 2/15:35 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 18/12C$ 577
Tue 31/127:10 a.m.YYZ - MDW
1 stop11h 44mMultiple Airlines
Wed 8/110:57 a.m.MDW - YYZ
1 stop5h 03mMultiple Airlines
Deal found 17/12C$ 597
Thu 19/1212:35 p.m.YYZ - MDW
1 stop6h 09mDelta
Sun 2/22:08 p.m.MDW - YYZ
1 stop7h 44mDelta
Deal found 18/12C$ 654
Wed 25/126:30 a.m.YYZ - MDW
1 stop11h 41mWestJet
Mon 30/1211:48 a.m.MDW - YYZ
2 stops19h 51mWestJet
Deal found 18/12C$ 670
Tue 31/1212:45 a.m.YEG - MDW
1 stop11h 39mMultiple Airlines
Tue 7/15:24 p.m.MDW - YEG
2 stops24h 26mMultiple Airlines
Deal found 17/12C$ 687
Mon 30/123:55 p.m.YVR - MDW
1 stop11h 38mMultiple Airlines
Mon 6/110:04 p.m.MDW - YVR
2 stops19h 39mMultiple Airlines
Deal found 17/12C$ 800
Tue 31/1212:05 a.m.YEG - MDW
2 stops15h 05mWestJet
Tue 7/12:08 p.m.MDW - YEG
2 stops11h 26mWestJet
Deal found 17/12C$ 803
Mon 23/129:20 a.m.YOW - MDW
2 stops15h 00mMultiple Airlines
Mon 30/126:00 a.m.MDW - YOW
1 stop7h 20mMultiple Airlines
Deal found 18/12C$ 901

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 629,999 searches. Data last updated 19 December 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 30/1

6:35 a.m.-12:46 p.m.

1 stop5h 11m

Chicago Midway

Mon 3/2

9:33 a.m.-8:53 p.m.

2 stops12h 20m

C$ 311

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 1/2

11:20 a.m.-12:10 p.m.

Nonstop1h 50m

Chicago Midway

Sat 8/2

1:05 p.m.-3:47 p.m.

Nonstop1h 42m

C$ 336

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 17/1

6:30 a.m.-12:10 p.m.

2 stops7h 40m

Chicago Midway

Fri 24/1

1:05 p.m.-10:25 p.m.

2 stops7h 20m

C$ 337

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Mon 13/1

12:45 a.m.-4:14 p.m.

1 stop14h 29m

Chicago Midway

Thu 30/1

7:21 p.m.-3:39 p.m.

2 stops21h 18m

C$ 350

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 16/1

10:10 a.m.-1:08 p.m.

1 stop3h 58m

Chicago Midway

Thu 23/1

9:34 a.m.-7:09 p.m.

1 stop8h 35m

C$ 357

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 12/1

11:20 a.m.-12:10 p.m.

Nonstop1h 50m

Chicago Midway

Fri 17/1

5:30 a.m.-4:48 p.m.

2 stops10h 18m

C$ 359

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 9/1

12:30 a.m.-11:51 a.m.

1 stop10h 21m

Chicago Midway

Mon 13/1

7:15 a.m.-10:55 p.m.

2 stops16h 40m

C$ 379

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 15/1

6:30 a.m.-5:47 p.m.

1 stop12h 17m

Chicago Midway

Fri 17/1

1:26 p.m.-11:11 p.m.

1 stop8h 45m

C$ 404

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 20/3

10:45 a.m.-4:40 p.m.

1 stop6h 55m

Chicago Midway

Sun 23/3

11:15 a.m.-4:50 p.m.

1 stop4h 35m

C$ 410

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 19/1

7:30 a.m.-9:32 p.m.

1 stop14h 02m

Chicago Midway

Fri 24/1

6:40 a.m.-3:10 p.m.

1 stop8h 30m

C$ 410

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/12

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, January is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 243). Flying from Canada to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 19 December 2024.

When flying from Canada to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 43.0 mm.

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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 19 December 2024.
Read through reviews of airlines operating flights from Canada to Chicago, such as Porter Airlines, WestJet and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,600 reviews
Check prices

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.0

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
8,600 reviews
Delta
8.0
Very good
8,600 reviews
Check prices

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.0

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
8,600 reviews
Check prices

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.0

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
388 reviews
Delta
8.0
Very good
8,600 reviews
Check prices

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.0

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
2,819 reviews
Delta
8.0
Very good
8,600 reviews
Check prices

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.0

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?

    One-way options have recently been found by users for as low as C$ 192 on Delta. Other airlines that offer cheap prices include Porter Airlines from C$ 202 and WestJet from C$ 237 one-way.

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

    While some choose either Toronto Pearson Intl - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago Midway, Toronto Island - Chicago Midway is the most popular route from Canada to Chicago Midway Airport.

  • 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, January is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 243). Flying from Canada to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 Canada to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pearson Intl to Midway flights
Vancouver Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Toronto Island to O'Hare Intl flights
Calgary to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Vancouver Intl to Midway flights
Winnipeg to O'Hare Intl flights
Calgary to Midway flights
Ottawa to Midway flights
Québec City to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights
Edmonton to Midway flights
Detroit to O'Hare Intl flights
Buffalo to O'Hare Intl flights
Québec City to Midway flights
Halifax to O'Hare Intl flights
Regina to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Halifax to Midway flights
Kelowna to O'Hare Intl flights
Saskatoon to Midway flights
Victoria to O'Hare Intl flights
London to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Kelowna to Midway flights
Victoria to Midway flights
Los Angeles to O'Hare Intl flights
St. John's to O'Hare Intl flights
Moncton to O'Hare Intl flights
Fort McMurray to O'Hare Intl flights
Seattle to O'Hare Intl flights
Mexico City to O'Hare Intl flights

Top 2 airlines flying from Canada to Midway

Discover the top 2 airlines 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 629,999 searches. Data last updated 19 December 2024.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 278AverageC$ 458FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 455AverageC$ 712FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Canada to Midway?

Cheapflights helps you search for flights from Canada to Midway via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Canada to Midway?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Canada.

Can Cheapflights find flights from Canada to Midway with no change fees?

Yes, we can. To see specific flights from Canada to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Canada to Midway become cheaper?

Yes! Start tracking prices for Canada to Midway flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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