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Cheap flights from Calgary to Chicago Midway Airport from C$ 193

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 26/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
30 Mar — 6 Apr1
1 adult

Cheap flight deals from Calgary to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) 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 25 March 2025.

Round-trip from

C$ 335

One-way from

C$ 193

Popular in

December

Cheapest in

February

Average price

C$ 382
Delta
  • Delta
  • 15/4-22/4
  • 3 total stops
  • 22h 01m total
  • Calgary to Chicago
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Delta
  • Delta
  • 26/4
  • 2 total stops
  • 10h 35m total
  • Calgary to Chicago
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Highest demand for flights based on searches. 16% potential increase in price (C$ 122 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 30 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Find flight deals from Calgary to Midway

Cheapest flights from Calgary to Midway
Explore the most affordable flight options available from Calgary to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 25 March 2025.

Tue 15/46:45 a.m.YYC - MDW
1 stop9h 34mDelta
Tue 22/49:20 a.m.MDW - YYC
2 stops12h 27mDelta
Deal found 24/3C$ 335
Fri 2/512:30 a.m.YYC - MDW
1 stop8h 03mMultiple Airlines
Fri 9/58:30 a.m.MDW - YYC
2 stops12h 10mMultiple Airlines
Deal found 24/3C$ 569
Sun 11/57:00 a.m.YYC - MDW
2 stops32h 54mPorter Airlines
Tue 13/59:40 a.m.MDW - YYC
2 stops12h 30mPorter Airlines
Deal found 24/3C$ 752
Tue 15/46:45 a.m.YYC - MDW
1 stop9h 34mWestJet
Tue 22/41:16 p.m.MDW - YYC
1 stop8h 31mWestJet
Deal found 24/3C$ 844

Cheapflights Fare Finder

Customize your flight search to find flights from Calgary 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 25 March 2025.
Use the filters below to find and compare flights from Calgary to Chicago Midway Airport that are best for you.

Fly from

Calgary

Fly to

Midway

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 15/4

6:45 a.m.-5:19 p.m.

1 stop9h 34m

Chicago Midway

Tue 22/4

9:20 a.m.-8:47 p.m.

2 stops12h 27m

C$ 335

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 2/5

12:30 a.m.-9:33 a.m.

1 stop8h 03m

Chicago Midway

Fri 9/5

8:30 a.m.-7:40 p.m.

2 stops12h 10m

C$ 569

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 11/5

7:00 a.m.-4:54 p.m.

2 stops32h 54m

Chicago Midway

Tue 13/5

9:40 a.m.-9:10 p.m.

2 stops12h 30m

C$ 752

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 15/4

6:45 a.m.-5:19 p.m.

1 stop9h 34m

Chicago Midway

Tue 22/4

1:16 p.m.-8:47 p.m.

1 stop8h 31m

C$ 844

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 26/4

6:45 a.m.-6:20 p.m.

2 stops10h 35m

C$ 193

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 9/5

12:30 a.m.-9:33 a.m.

1 stop8h 03m

C$ 231

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 1/6

7:00 a.m.-4:54 p.m.

2 stops32h 54m

C$ 434

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 9/5

1:00 a.m.-9:14 p.m.

2 stops19h 14m

C$ 436

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/3

Best time to book a flight from Calgary to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Calgary 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 Calgary to Chicago Midway Airport

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 25 March 2025.
To help decide which airline to fly from Calgary to Chicago, see what other customers have to say about Delta, Porter Airlines and WestJet. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,890 reviews
Check prices

Overall

8.0

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

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
7,890 reviews
Delta
8.0
Very good
7,890 reviews
Check prices

Overall

8.0

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

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
275 reviews
Delta
8.0
Very good
7,890 reviews
Check prices

Overall

8.0

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

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
2,785 reviews
Delta
8.0
Very good
7,890 reviews
Check prices

Overall

8.0

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

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 Calgary to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Calgary to Chicago Midway?

    Calgary (YYC), located 9.3 km from the city centre, is the airport you fly out of when you book flights from Calgary to Chicago Midway. 0 airlines have flights from Calgary to Chicago Midway on a regular basis. Booking flights from Calgary to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

  • What are the cheapest airlines flying from Calgary to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Calgary to Chicago Midway Airport round-trip from C$ 335. Other airlines that can offer you cheap pricing are Porter Airlines, from C$ 752, and WestJet, from C$ 844.

  • What are the cheapest airlines to fly from Calgary to Chicago Midway Airport one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as C$ 193. However, be on the lookout for offers from Porter Airlines and WestJet, as they are both options that can get you from Calgary to Chicago Midway Airport for a low price.

  • Can I find deals for flights from Calgary to Midway that include hotel bookings?

    Yes. In addition to deals on Calgary to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Calgary to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Calgary to Midway.

  • Can I find deals for business class flights from Calgary to Midway?

    Yes. Cheapflights offers flight deals from Calgary 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 Calgary to Chicago Midway Airport?

    Currently, January is the cheapest month in which you can book a flight from Calgary to Chicago Midway Airport (average of C$ 243). Flying from Calgary 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.

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Why should you use Cheapflights to find cheap flight tickets from Calgary 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 Calgary.

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

Yes, we can. To see specific flights from Calgary 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 Calgary to Midway become cheaper?

Yes, Cheapflights offers price alerts on Calgary to Midway flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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