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Cheap flights from Calgary to Chicago Midway Airport from C$ 198

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 29/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
22 Jan — 29 Jan1
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 17 January 2025.

Round-trip from

C$ 325

One-way from

C$ 198
Delta
  • Delta
  • 21/2-25/2
  • 3 total stops
  • 22h 28m total
  • Calgary to Chicago
Search Deals
Delta
  • Delta
  • 29/1
  • 1 total stop
  • 5h 11m total
  • Calgary to Chicago
Search Deals

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 17 January 2025.

Fri 21/26:35 a.m.YYC - MDW
1 stop10h 08mDelta
Tue 25/29:33 a.m.MDW - YYC
2 stops12h 20mDelta
Deal found 14/1C$ 325
Thu 20/26:35 a.m.YYC - MDW
1 stop10h 08mMultiple Airlines
Thu 27/25:10 a.m.MDW - YYC
2 stops17h 42mMultiple Airlines
Deal found 16/1C$ 451
Thu 10/47:44 a.m.YYC - MDW
1 stop9h 34mWestJet
Sat 12/411:22 a.m.MDW - YYC
2 stops9h 18mWestJet
Deal found 16/1C$ 719
Thu 10/47:40 a.m.YYC - MDW
2 stops25h 40mPorter Airlines
Sat 12/412:55 p.m.MDW - YYC
2 stops9h 36mPorter Airlines
Deal found 15/1C$ 753

Find flights from Calgary to Midway within your budget

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 17 January 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 21/2

6:35 a.m.-5:43 p.m.

1 stop10h 08m

Chicago Midway

Tue 25/2

9:33 a.m.-8:53 p.m.

2 stops12h 20m

C$ 325

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 20/2

6:35 a.m.-5:43 p.m.

1 stop10h 08m

Chicago Midway

Thu 27/2

5:10 a.m.-9:52 p.m.

2 stops17h 42m

C$ 451

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 10/4

7:44 a.m.-6:18 p.m.

1 stop9h 34m

Chicago Midway

Sat 12/4

11:22 a.m.-7:40 p.m.

2 stops9h 18m

C$ 719

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 10/4

7:40 a.m.-10:20 a.m.

2 stops25h 40m

Chicago Midway

Sat 12/4

12:55 p.m.-9:31 p.m.

2 stops9h 36m

C$ 753

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 29/1

6:35 a.m.-12:46 p.m.

1 stop5h 11m

C$ 198

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 29/1

9:20 a.m.-12:17 a.m.

2 stops13h 57m

C$ 237

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 6/3

6:35 a.m.-5:43 p.m.

1 stop10h 08m

C$ 404

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 31/3

7:40 a.m.-10:20 a.m.

2 stops25h 40m

C$ 433

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/1

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.

Travel insights for flights from Calgary to Midway

Get recent, data-driven insights about flights from Calgary to Midway including ideal travel times, pricing trends, and more.

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 17 January 2025.
To help decide which airline to fly from Calgary to Chicago, see what other customers have to say about Delta 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
8,511 reviews
Check prices

Entertainment

7.9

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,511 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Entertainment

7.9

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines
7.9
Good
276 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Entertainment

7.9

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

WestJet
7.2
Good
2,824 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Entertainment

7.9

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

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$ 325. Other airlines that can offer you cheap pricing are WestJet, from C$ 730, and Porter Airlines, from C$ 753.

  • 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$ 198. However, be on the lookout for offers from WestJet and Porter Airlines, 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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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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