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Cheap flights from Calgary to Chicago Midway Airport from C$ 191

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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
3 Aug — 10 Aug1
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 29 July 2025.

Round-trip from

C$ 398

One-way from

C$ 191

Popular in

December

Cheapest in

April

Average price

C$ 498
Delta
  • Delta
  • 10/12-15/12
  • 3 total stops
  • 30h 01m total
  • Calgary to Chicago
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Delta
  • Delta
  • 10/9
  • 1 total stop
  • 5h 23m total
  • Calgary to Chicago
Search Deals
Highest demand for flights based on searches. 23% potential increase in price (C$ 162 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 32 potential savings vs. average RT price).
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Average for round-trip flights in July 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 29 July 2025.

Wed 10/128:55 a.m.YYC - MDW
1 stop11h 49mDelta
Mon 15/126:00 a.m.MDW - YYC
2 stops18h 12mDelta
Deal found 27/7C$ 398
Wed 10/912:30 a.m.YYC - MDW
1 stop14h 28mMultiple Airlines
Wed 17/99:00 a.m.MDW - YYC
1 stop12h 00mMultiple Airlines
Deal found 27/7C$ 451
Wed 10/98:00 a.m.YYC - MDW
2 stops23h 39mPorter Airlines
Mon 15/99:35 a.m.MDW - YYC
2 stops13h 53mPorter Airlines
Deal found 27/7C$ 506
Sat 6/97:00 a.m.YYC - MDW
2 stops13h 12mWestJet
Mon 8/910:31 a.m.MDW - YYC
2 stops11h 21mWestJet
Deal found 29/7C$ 834

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 29 July 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 10/12

8:55 a.m.-9:44 p.m.

1 stop11h 49m

Chicago Midway

Mon 15/12

6:00 a.m.-11:12 p.m.

2 stops18h 12m

C$ 398

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 10/9

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

1 stop14h 28m

Chicago Midway

Wed 17/9

9:00 a.m.-8:00 p.m.

1 stop12h 00m

C$ 451

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 10/9

8:00 a.m.-8:39 a.m.

2 stops23h 39m

Chicago Midway

Mon 15/9

9:35 a.m.-10:28 p.m.

2 stops13h 53m

C$ 506

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 6/9

7:00 a.m.-9:12 p.m.

2 stops13h 12m

Chicago Midway

Mon 8/9

10:31 a.m.-8:52 p.m.

2 stops11h 21m

C$ 834

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 10/9

6:40 a.m.-1:03 p.m.

1 stop5h 23m

C$ 191

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 20/9

12:45 a.m.-4:24 p.m.

1 stop14h 39m

C$ 207

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 10/9

8:00 a.m.-8:39 a.m.

2 stops23h 39m

C$ 235

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/9

1:00 a.m.-5:37 p.m.

2 stops15h 37m

C$ 396

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/7

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$ 281.

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: 2h 45m.

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.

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 29 July 2025.
Read through reviews of airlines operating flights from Calgary to Chicago Midway Airport, such as Porter Airlines,Delta, andWestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
317 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
317 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,977 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,973 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Food

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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$ 398. Other airlines that can offer you cheap pricing are Porter Airlines, from C$ 506, and WestJet, from C$ 834.

  • 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$ 191. 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, June is the cheapest month in which you can book a flight from Calgary to Chicago Midway Airport (average of C$ 233). 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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