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Cheap flights from Calgary to Chicago Midway Airport from C$ 190

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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Calgary to Midway

Enter your travel dates to find the best prices.

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 12 December 2025.

Mon 29/127:35 p.m.YYC - MDW
1 stop13h 44mMultiple Airlines
Wed 31/122:16 p.m.MDW - YYC
2 stops23h 04mMultiple Airlines
Deal found 10/12C$ 1,066
Mon 29/1211:40 p.m.YYC - MDW
2 stops16h 39mWestJet
Wed 31/129:50 a.m.MDW - YYC
2 stops31h 10mWestJet
Deal found 10/12C$ 1,121
Thu 11/126:35 a.m.YYC - MDW
1 stop10h 43mWestJet
Mon 15/1210:49 a.m.MDW - YYC
1 stop9h 20mWestJet
Deal found 10/12C$ 1,241
Mon 15/126:35 a.m.YYC - MDW
1 stop5h 35mWestJet
Wed 17/1210:49 a.m.MDW - YYC
1 stop9h 20mWestJet
Deal found 10/12C$ 1,382
Thu 11/124:30 p.m.YYC - MDW
1 stop16h 35mMultiple Airlines
Mon 15/1211:00 a.m.MDW - YYC
1 stop9h 35mMultiple Airlines
Deal found 11/12C$ 2,226

Find 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 12 December 2025.

Round-trip from

C$ 308

One-way from

C$ 190

Popular in

July

Cheapest in

April

Average price

C$ 393
Delta
  • Delta
  • 14/1-18/1
  • 3 total stops
  • 19h 51m total
  • Calgary to Chicago
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Delta
  • Delta
  • 10/1
  • 1 total stop
  • 8h 46m total
  • Calgary to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 12 December 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

Wed 14/1

6:30 a.m.-1:09 p.m.

1 stop5h 39m

Chicago Midway

Sun 18/1

9:50 a.m.-11:02 p.m.

2 stops14h 12m

C$ 308

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 24/1

6:30 a.m.-4:16 p.m.

1 stop8h 46m

Chicago Midway

Sat 31/1

11:45 a.m.-8:54 p.m.

1 stop10h 09m

C$ 335

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 25/1

6:30 a.m.-1:09 p.m.

1 stop5h 39m

Chicago Midway

Sun 1/2

1:51 p.m.-8:54 p.m.

1 stop8h 03m

C$ 356

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 26/5

9:15 a.m.-6:31 p.m.

1 stop8h 16m

Chicago Midway

Sat 30/5

9:20 a.m.-6:40 p.m.

2 stops10h 20m

C$ 371

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 22/1

12:30 a.m.-11:45 a.m.

1 stop10h 15m

Chicago Midway

Fri 30/1

5:01 p.m.-4:15 p.m.

2 stops24h 14m

C$ 408

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 24/1

12:30 a.m.-11:45 a.m.

1 stop10h 15m

Chicago Midway

Sun 1/2

5:01 p.m.-4:15 p.m.

2 stops24h 14m

C$ 412

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 15/1

8:55 a.m.-10:07 p.m.

1 stop12h 12m

Chicago Midway

Wed 21/1

9:32 a.m.-8:54 p.m.

2 stops12h 22m

C$ 452

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 10/1

6:30 a.m.-4:16 p.m.

1 stop8h 46m

C$ 190

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 27/2

6:30 a.m.-1:07 p.m.

1 stop5h 37m

C$ 190

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 15/1

7:35 p.m.-11:47 a.m.

1 stop15h 12m

C$ 210

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 14 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 cheapest layover airport for flights from Calgary to Chicago Midway Airport?

Average round-trip fare for 1-stop flights from Calgary to Chicago Midway Airport, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of C$ 283.

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 39m. 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.

See more FAQs

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

Deals for Calgary to Midway flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

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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