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Cheap flights from Canada to Chicago Midway Airport from C$ 166

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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
28 Apr — 5 May1
1 adult

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 23 April 2025.

Round-trip from

C$ 264

One-way from

C$ 166

Popular in

December

Cheapest in

March

Average price

C$ 348

Good round-trip deal

C$ 267 or less

Good one-way deal

C$ 165 or less
Porter Airlines
  • Porter Airlines
  • 6/6-13/6
  • Nonstop
  • 3h 31m total
  • Canada to Chicago
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Porter Airlines
  • Porter Airlines
  • 4/6
  • 1 total stop
  • 4h 44m total
  • Canada to Chicago
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Highest demand for flights based on searches. 4% potential increase in price (C$ 26 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 6 potential savings vs. average RT price).
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Average for round-trip flights in April 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 23 April 2025.

Fri 6/63:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Fri 13/65:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/4C$ 264
Sun 11/57:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Thu 15/59:40 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 22/4C$ 268
Thu 22/56:30 a.m.YYZ - MDW
1 stop7h 45mDelta
Mon 26/59:16 a.m.MDW - YYZ
1 stop6h 59mDelta
Deal found 22/4C$ 293
Thu 8/57:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sat 10/59:40 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 21/4C$ 312
Thu 8/510:45 a.m.YUL - MDW
1 stop6h 39mPorter Airlines
Mon 12/59:40 a.m.MDW - YUL
1 stop5h 20mPorter Airlines
Deal found 22/4C$ 315
Thu 5/66:00 a.m.YUL - MDW
1 stop3h 40mDelta
Fri 6/64:15 p.m.MDW - YUL
1 stop6h 39mDelta
Deal found 22/4C$ 329
Tue 3/66:30 a.m.YYC - MDW
1 stop10h 15mDelta
Tue 10/61:47 p.m.MDW - YYC
1 stop8h 08mDelta
Deal found 22/4C$ 346
Tue 3/69:25 a.m.YEG - MDW
1 stop7h 20mDelta
Tue 24/69:21 a.m.MDW - YEG
1 stop7h 37mDelta
Deal found 21/4C$ 357
Wed 7/512:25 p.m.YOW - MDW
1 stop4h 59mPorter Airlines
Mon 12/59:15 a.m.MDW - YOW
1 stop6h 19mPorter Airlines
Deal found 22/4C$ 359
Wed 21/512:30 p.m.YYZ - MDW
1 stop6h 15mWestJet
Wed 28/512:48 p.m.MDW - YYZ
1 stop8h 08mWestJet
Deal found 21/4C$ 391
Thu 22/51:10 p.m.YUL - MDW
1 stop4h 14mMultiple Airlines
Thu 29/512:48 p.m.MDW - YUL
2 stops10h 49mMultiple Airlines
Deal found 22/4C$ 400
Thu 5/69:35 a.m.YEG - MDW
1 stop12h 43mMultiple Airlines
Tue 24/611:39 a.m.MDW - YEG
1 stop9h 09mMultiple Airlines
Deal found 21/4C$ 422

Cheapflights Fare Finder

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

Fly from

Canada

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 6/6

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Fri 13/6

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 264

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 11/5

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Thu 15/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 268

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 22/5

3:50 p.m.-6:45 p.m.

1 stop3h 55m

Chicago Midway

Sun 1/6

1:55 p.m.-11:14 p.m.

1 stop8h 19m

C$ 293

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 8/5

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Sat 10/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 312

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 8/5

10:45 a.m.-4:24 p.m.

1 stop6h 39m

Chicago Midway

Mon 12/5

9:40 a.m.-4:00 p.m.

1 stop5h 20m

C$ 315

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 5/6

6:00 a.m.-8:40 a.m.

1 stop3h 40m

Chicago Midway

Fri 6/6

4:15 p.m.-11:54 p.m.

1 stop6h 39m

C$ 329

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 3/6

6:30 a.m.-5:45 p.m.

1 stop10h 15m

Chicago Midway

Tue 10/6

1:47 p.m.-8:55 p.m.

1 stop8h 08m

C$ 346

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Tue 3/6

9:25 a.m.-5:45 p.m.

1 stop7h 20m

Chicago Midway

Tue 24/6

9:21 a.m.-3:58 p.m.

1 stop7h 37m

C$ 357

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 7/5

12:25 p.m.-4:24 p.m.

1 stop4h 59m

Chicago Midway

Mon 12/5

9:15 a.m.-4:34 p.m.

1 stop6h 19m

C$ 359

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 21/5

12:30 p.m.-5:45 p.m.

1 stop6h 15m

Chicago Midway

Wed 28/5

12:48 p.m.-9:56 p.m.

1 stop8h 08m

C$ 391

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/4

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.

Cheapflights Insights

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

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 23 April 2025.

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 23 April 2025.
Read through reviews of airlines operating flights from Canada to Chicago, such as Porter Airlines, Delta and Air Transat. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
284 reviews
Check prices

Crew

8.8

Food

7.6

Overall

8.0

Entertainment

7.0

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
284 reviews
Porter Airlines
8.0
Very good
284 reviews
Check prices

Crew

8.8

Food

7.6

Overall

8.0

Entertainment

7.0

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,920 reviews
Porter Airlines
8.0
Very good
284 reviews
Check prices

Crew

8.8

Food

7.6

Overall

8.0

Entertainment

7.0

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Transat
7.8
Good
385 reviews
Porter Airlines
8.0
Very good
284 reviews
Check prices

Crew

8.8

Food

7.6

Overall

8.0

Entertainment

7.0

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,815 reviews
Porter Airlines
8.0
Very good
284 reviews
Check prices

Crew

8.8

Food

7.6

Overall

8.0

Entertainment

7.0

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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$ 166 on Porter Airlines. Other airlines that offer cheap prices include Delta from C$ 185 and Air Transat from C$ 188 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

Browse thousands of different options on Cheapflights for your next trip

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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
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Pierre Elliott Trudeau Intl to O'Hare Intl flights
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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 23 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 260AverageC$ 453FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 476AverageC$ 677FlexibilityNo 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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