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Cheap flights from Calgary to Chicago Midway Airport from C$ 173

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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
27 Nov — 4 Dec1
1 adult
1 adult, Economy, 0 bags

Find 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 28 October 2025.

Wed 24/126:30 a.m.YYC - MDW
1 stop9h 49mDelta
Wed 31/1211:48 a.m.MDW - YYC
1 stop10h 18mDelta
Deal found 27/10C$ 310
Wed 24/126:30 a.m.YYC - MDW
1 stop9h 49mDelta
Tue 30/126:00 a.m.MDW - YYC
2 stops16h 06mDelta
Deal found 27/10C$ 359
Tue 28/106:45 a.m.YYC - MDW
1 stop5h 23mDelta
Wed 29/101:08 p.m.MDW - YYC
2 stops10h 54mDelta
Deal found 27/10C$ 373
Sat 1/1112:30 a.m.YYC - MDW
1 stop9h 15mDelta
Sun 9/119:34 a.m.MDW - YYC
2 stops12h 19mDelta
Deal found 28/10C$ 420
Sat 1/116:45 a.m.YYC - MDW
1 stop5h 23mDelta
Mon 3/111:48 p.m.MDW - YYC
1 stop7h 59mDelta
Deal found 28/10C$ 442
Thu 20/1112:30 a.m.YYC - MDW
1 stop8h 22mDelta
Mon 24/111:47 p.m.MDW - YYC
1 stop8h 06mDelta
Deal found 27/10C$ 526
Fri 28/1112:15 a.m.YYC - MDW
1 stop10h 35mMultiple Airlines
Tue 2/122:49 p.m.MDW - YYC
1 stop21h 55mMultiple Airlines
Deal found 28/10C$ 559
Fri 12/128:55 a.m.YYC - MDW
1 stop9h 47mMultiple Airlines
Fri 19/126:12 a.m.MDW - YYC
2 stops15h 04mMultiple Airlines
Deal found 28/10C$ 568
Thu 13/118:55 a.m.YYC - MDW
1 stop8h 44mMultiple Airlines
Sun 16/116:06 p.m.MDW - YYC
2 stops42h 38mMultiple Airlines
Deal found 27/10C$ 611
Fri 14/1112:20 p.m.YYC - MDW
1 stop23h 17mMultiple Airlines
Sun 16/116:06 p.m.MDW - YYC
2 stops26h 03mMultiple Airlines
Deal found 27/10C$ 614

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 28 October 2025.

Round-trip from

C$ 310

One-way from

C$ 173

Popular in

December

Cheapest in

April

Average price

C$ 452
Delta
  • Delta
  • 24/12-31/12
  • 2 total stops
  • 20h 07m total
  • Calgary to Chicago
Search Deals
12/12
  • 12/12
  • 2 total stops
  • 22h 37m total
  • Calgary to Chicago
Search Deals
Highest demand for flights based on searches. 23% potential increase in price (C$ 166 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 28 October 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 24/12

6:30 a.m.-5:19 p.m.

1 stop9h 49m

Chicago Midway

Tue 30/12

11:48 a.m.-9:06 p.m.

1 stop10h 18m

C$ 310

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/1

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

1 stop5h 39m

Chicago Midway

Sat 28/2

10:35 a.m.-11:15 p.m.

2 stops13h 40m

C$ 310

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 31/1

10:00 a.m.-11:25 p.m.

2 stops12h 25m

Chicago Midway

Sat 28/2

6:00 a.m.-7:09 p.m.

1 stop14h 09m

C$ 502

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 28/11

12:15 a.m.-11:50 a.m.

1 stop10h 35m

Chicago Midway

Tue 2/12

2:49 p.m.-11:44 a.m.

1 stop21h 55m

C$ 559

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 12/12

8:55 a.m.-7:42 p.m.

1 stop9h 47m

Chicago Midway

Fri 19/12

6:12 a.m.-8:16 p.m.

2 stops15h 04m

C$ 568

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 20/11

12:30 a.m.-9:52 a.m.

1 stop8h 22m

Chicago Midway

Mon 24/11

1:47 p.m.-8:53 p.m.

1 stop8h 06m

C$ 578

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 31/1

6:30 a.m.-10:26 p.m.

2 stops14h 56m

Chicago Midway

Mon 2/3

10:35 a.m.-7:09 p.m.

1 stop9h 34m

C$ 594

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 11/12

8:55 a.m.-6:08 p.m.

1 stop8h 13m

C$ 185

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 18/11

12:30 a.m.-12:41 p.m.

1 stop11h 11m

C$ 185

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 20/11

6:35 a.m.-1:07 p.m.

1 stop5h 32m

C$ 192

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/10

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 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 9h 49m. 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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