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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 21/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
6 Apr — 13 Apr1
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 1 April 2025.

Round-trip from

C$ 286

One-way from

C$ 178

Popular in

December

Cheapest in

April

Average price

C$ 336

Good round-trip deal

C$ 276 or less

Good one-way deal

C$ 172 or less
Porter Airlines
  • Porter Airlines
  • 23/4-30/4
  • Nonstop
  • 3h 32m total
  • Canada to Chicago
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Porter Airlines
  • Porter Airlines
  • 21/4
  • Nonstop
  • 1h 50m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 25 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 1 April 2025.

Wed 23/49:30 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 30/411:15 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 31/3C$ 286
Sun 11/56:30 a.m.YYC - MDW
1 stop5h 45mDelta
Tue 13/51:55 p.m.MDW - YYC
1 stop7h 45mDelta
Deal found 31/3C$ 313
Thu 8/510:45 a.m.YUL - MDW
1 stop6h 39mPorter Airlines
Sun 11/59:40 a.m.MDW - YUL
1 stop5h 20mPorter Airlines
Deal found 31/3C$ 343
Wed 14/54:05 p.m.YTZ - MDW
Nonstop1h 49mAir Transat
Wed 21/59:40 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 30/3C$ 349
Fri 2/511:00 p.m.YVR - MDW
1 stop8h 33mMultiple Airlines
Tue 6/59:34 a.m.MDW - YVR
1 stop13h 18mMultiple Airlines
Deal found 30/3C$ 353
Thu 1/53:35 p.m.YTZ - MDW
Nonstop1h 49mMultiple Airlines
Sun 4/59:40 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 30/3C$ 356
Thu 24/43:59 p.m.YYZ - MDW
1 stop3h 21mDelta
Sun 27/49:20 a.m.MDW - YYZ
1 stop4h 49mDelta
Deal found 31/3C$ 359
Sat 10/512:30 a.m.YYC - MDW
1 stop12h 04mMultiple Airlines
Tue 13/59:34 a.m.MDW - YYC
1 stop11h 31mMultiple Airlines
Deal found 31/3C$ 362
Thu 22/59:15 a.m.YHZ - MDW
2 stops9h 09mPorter Airlines
Tue 27/59:40 a.m.MDW - YHZ
2 stops11h 44mPorter Airlines
Deal found 31/3C$ 383
Wed 7/56:00 a.m.YUL - MDW
1 stop3h 40mDelta
Sat 10/55:25 p.m.MDW - YUL
1 stop4h 51mDelta
Deal found 31/3C$ 393
Thu 1/59:35 a.m.YEG - MDW
1 stop13h 04mMultiple Airlines
Thu 8/58:30 a.m.MDW - YEG
1 stop12h 18mMultiple Airlines
Deal found 30/3C$ 393
Sat 24/58:00 p.m.YYZ - MDW
2 stops14h 40mWestJet
Tue 27/59:20 a.m.MDW - YYZ
1 stop8h 11mWestJet
Deal found 31/3C$ 418

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 1 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

Wed 23/4

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

Chicago Midway

Wed 30/4

11:15 a.m.-1:57 p.m.

Nonstop1h 42m

C$ 286

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 11/5

6:30 a.m.-1:15 p.m.

1 stop5h 45m

Chicago Midway

Tue 13/5

1:55 p.m.-8:40 p.m.

1 stop7h 45m

C$ 313

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

Sun 11/5

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

1 stop5h 20m

C$ 343

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 14/5

4:05 p.m.-4:54 p.m.

Nonstop1h 49m

Chicago Midway

Wed 21/5

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

Nonstop1h 42m

C$ 349

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 2/5

11:00 p.m.-9:33 a.m.

1 stop8h 33m

Chicago Midway

Tue 6/5

9:34 a.m.-8:52 p.m.

1 stop13h 18m

C$ 353

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/5

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

Nonstop1h 49m

Chicago Midway

Sun 4/5

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

Nonstop1h 42m

C$ 356

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 24/4

3:59 p.m.-6:20 p.m.

1 stop3h 21m

Chicago Midway

Sun 27/4

9:20 a.m.-3:09 p.m.

1 stop4h 49m

C$ 359

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 10/5

12:30 a.m.-1:34 p.m.

1 stop12h 04m

Chicago Midway

Tue 13/5

9:34 a.m.-8:05 p.m.

1 stop11h 31m

C$ 362

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 22/5

9:15 a.m.-4:24 p.m.

2 stops9h 09m

Chicago Midway

Tue 27/5

9:40 a.m.-11:24 p.m.

2 stops11h 44m

C$ 383

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 7/5

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

1 stop3h 40m

Chicago Midway

Sat 10/5

5:25 p.m.-11:16 p.m.

1 stop4h 51m

C$ 393

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/3

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 1 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 1 April 2025.
Read through reviews of airlines operating flights from Canada to Chicago, such as Delta, Porter Airlines and Air Transat. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,899 reviews
Check prices

Food

7.3

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,899 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Food

7.3

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Porter Airlines
7.9
Good
277 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Food

7.3

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Transat
7.8
Good
381 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Food

7.3

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,789 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Food

7.3

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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$ 178 on Porter Airlines. Other airlines that offer cheap prices include Delta from C$ 194 and Air Transat from C$ 211 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
Vancouver 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
Pierre Elliott Trudeau Intl to Midway flights
Calgary to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
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Region of Waterloo Intl to O'Hare Intl flights
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Halifax to Midway flights
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Victoria to Midway flights
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Comox to O'Hare Intl flights
Saskatoon to Midway 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 1 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 270AverageC$ 478FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 495AverageC$ 703FlexibilityNo 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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