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Cheap flights from Calgary to Chicago Midway Airport from C$ 180

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 24/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
11 Oct — 18 Oct1
1 adult
1 adult, Economy

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 11 September 2025.

Round-trip from

C$ 309

One-way from

C$ 180

Popular in

December

Cheapest in

April

Average price

C$ 319
Delta
  • Delta
  • 25/10-1/11
  • 2 total stops
  • 10h 57m total
  • Calgary to Chicago
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24/10
  • 24/10
  • 2 total stops
  • 15h 46m total
  • Calgary to Chicago
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Highest demand for flights based on searches. 23% potential increase in price (C$ 166 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease (C$ 33 potential savings vs. average RT price).
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Average for round-trip flights in September 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 11 September 2025.

Sat 25/106:45 a.m.YYC - MDW
1 stop5h 23mDelta
Sat 1/119:20 a.m.MDW - YYC
1 stop5h 34mDelta
Deal found 10/9C$ 309
Wed 19/116:20 a.m.YYC - MDW
1 stop5h 47mDelta
Wed 7/12:00 p.m.MDW - YYC
1 stop7h 58mDelta
Deal found 11/9C$ 321
Wed 19/116:20 a.m.YYC - MDW
1 stop5h 47mDelta
Mon 12/12:00 p.m.MDW - YYC
1 stop7h 58mDelta
Deal found 11/9C$ 345
Wed 1/106:40 a.m.YYC - MDW
1 stop9h 55mDelta
Tue 4/119:35 a.m.MDW - YYC
2 stops12h 12mDelta
Deal found 11/9C$ 352
Tue 30/97:00 a.m.YYC - MDW
2 stops31h 58mMultiple Airlines
Tue 7/108:05 a.m.MDW - YYC
1 stop12h 55mMultiple Airlines
Deal found 10/9C$ 363
Mon 27/106:45 a.m.YYC - MDW
1 stop9h 58mDelta
Thu 30/109:20 a.m.MDW - YYC
1 stop5h 34mDelta
Deal found 10/9C$ 380
Wed 1/1012:30 a.m.YYC - MDW
1 stop14h 28mMultiple Airlines
Sun 5/106:30 a.m.MDW - YYC
1 stop12h 51mMultiple Airlines
Deal found 10/9C$ 400
Mon 27/106:30 a.m.YYC - MDW
2 stops14h 16mMultiple Airlines
Thu 30/108:30 a.m.MDW - YYC
1 stop15h 22mMultiple Airlines
Deal found 10/9C$ 406
Thu 2/1012:30 a.m.YYC - MDW
1 stop22h 11mMultiple Airlines
Thu 9/106:24 p.m.MDW - YYC
2 stops23h 07mMultiple Airlines
Deal found 9/9C$ 409

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 11 September 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

Sat 25/10

6:45 a.m.-1:08 p.m.

1 stop5h 23m

Chicago Midway

Sat 1/11

9:20 a.m.-1:54 p.m.

1 stop5h 34m

C$ 309

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 26/10

6:45 a.m.-1:08 p.m.

1 stop5h 23m

Chicago Midway

Sat 1/11

10:40 a.m.-11:02 p.m.

2 stops13h 22m

C$ 309

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 19/11

6:20 a.m.-1:07 p.m.

1 stop5h 47m

Chicago Midway

Wed 7/1

2:00 p.m.-8:58 p.m.

1 stop7h 58m

C$ 321

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 23/11

6:20 a.m.-1:07 p.m.

1 stop5h 47m

Chicago Midway

Wed 7/1

2:00 p.m.-8:58 p.m.

1 stop7h 58m

C$ 321

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 23/11

6:20 a.m.-1:07 p.m.

1 stop5h 47m

Chicago Midway

Mon 12/1

2:00 p.m.-8:58 p.m.

1 stop7h 58m

C$ 345

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 19/11

6:20 a.m.-1:07 p.m.

1 stop5h 47m

Chicago Midway

Mon 12/1

2:00 p.m.-8:58 p.m.

1 stop7h 58m

C$ 345

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 30/9

7:00 a.m.-3:58 p.m.

2 stops31h 58m

Chicago Midway

Tue 7/10

8:05 a.m.-8:00 p.m.

1 stop12h 55m

C$ 363

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 27/10

6:45 a.m.-5:43 p.m.

1 stop9h 58m

Chicago Midway

Thu 30/10

9:20 a.m.-1:54 p.m.

1 stop5h 34m

C$ 380

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 1/10

12:30 a.m.-3:58 p.m.

1 stop14h 28m

Chicago Midway

Sun 5/10

6:30 a.m.-6:21 p.m.

1 stop12h 51m

C$ 400

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 25/10

10:00 a.m.-10:47 p.m.

1 stop11h 47m

C$ 188

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 18 results
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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

What’s the top layover airport for flights from Calgary to Chicago Midway Airport?

Share of one-stop round-trip flights from Calgary to Chicago Midway Airport chosen by Cheapflights users in the past 12 months, using the same layover each way.

Minneapolis (MSP) – chosen by Cheapflights users on 67% of one-stop itineraries from Calgary to Chicago Midway Airport on Cheapflights.

What’s the fastest layover option from Calgary to Chicago Midway Airport?

Shortest average travel time for 1-stop one-way flights from Calgary to Chicago Midway Airport, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 5h 31m.

What’s the fastest layover option from Calgary to Chicago Midway Airport?

Shortest average travel time for 1-stop one-way flights from Calgary to Chicago Midway Airport, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 5h 31m.

Which airport typically offers the quickest layover for flights from Calgary to Chicago Midway Airport?

Average layover duration for 1-stop one-way flights from Calgary to Chicago Midway Airport, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 1h 33m.

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.

  • How long is the flight from Calgary to Chicago Midway Airport?

    There are many flights that can get you from Calgary to Chicago Midway Airport in 5h 23m. Fly via Delta to get the fastest option. There are 2247 km between Calgary and Chicago Midway Airport.

  • 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, September is the cheapest month in which you can book a flight from Calgary to Chicago Midway Airport (average of C$ 209). 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.

See more FAQs

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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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