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Cheap flights from Chicago to Calgary from C$ 107

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 26/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYC
4 May — 11 May1
1 adult

Cheapflights Tip: The best prices from Chicago to Calgary are usually found in May or September, booked 22 days in advance, depart on a Wednesday or Monday and return on a Thursday

Cheap flight deals from Chicago to Calgary

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Calgary (YYC). 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 April 2025.

Round-trip from

C$ 229

One-way from

C$ 107

Popular in

December

Cheapest in

May

Average price

C$ 438

Good round-trip deal

C$ 150 or less

Good one-way deal

C$ 101 or less
Air Canada
  • Air Canada
  • 29/5-29/5
  • 2 total stops
  • 18h 51m total
  • Chicago to Calgary
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United Airlines
  • United Airlines
  • 26/5
  • 1 total stop
  • 12h 11m total
  • Chicago to Calgary
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Highest demand for flights based on searches. 22% potential increase in price (C$ 176 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease (C$ 49 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Calgary.
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Price to beat on a one-way flight from Chicago (CHI) to Calgary.
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Find flight deals from Chicago to Calgary

Cheapest flights from Chicago to Calgary
Explore the most affordable flight options available from Chicago to Calgary. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 29 April 2025.

Thu 29/52:16 p.m.ORD - YYC
1 stop9h 22mAir Canada
Thu 29/512:55 a.m.YYC - ORD
1 stop9h 29mAir Canada
Deal found 28/4C$ 229
Tue 27/58:45 a.m.ORD - YYC
1 stop14h 03mUnited Airlines
Tue 3/612:38 p.m.YYC - ORD
Nonstop3h 32mUnited Airlines
Deal found 28/4C$ 263
Sun 25/55:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Tue 3/612:15 p.m.YYC - ORD
Nonstop3h 29mWestJet
Deal found 28/4C$ 267
Fri 9/58:45 a.m.ORD - YYC
Nonstop3h 56mMultiple Airlines
Mon 12/511:55 p.m.YYC - ORD
1 stop7h 55mMultiple Airlines
Deal found 27/4C$ 305
Wed 13/81:55 p.m.ORD - YYC
1 stop10h 08mDelta
Fri 29/86:35 a.m.YYC - ORD
1 stop9h 15mDelta
Deal found 28/4C$ 348
Sun 25/59:20 a.m.MDW - YYC
2 stops14h 41mDelta
Tue 27/56:30 a.m.YYC - MDW
1 stop5h 45mDelta
Deal found 27/4C$ 362
Thu 14/88:34 p.m.ORD - YYC
Nonstop3h 55mAmerican Airlines
Wed 20/81:29 p.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
Deal found 28/4C$ 366
Tue 13/59:34 a.m.MDW - YYC
1 stop11h 31mMultiple Airlines
Tue 20/55:30 p.m.YYC - MDW
1 stop18h 47mMultiple Airlines
Deal found 28/4C$ 450
Wed 28/59:40 a.m.MDW - YYC
2 stops12h 35mPorter Airlines
Mon 2/611:55 p.m.YYC - MDW
1 stop15h 29mPorter Airlines
Deal found 28/4C$ 495

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Calgary 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 April 2025.
Use the filters below to find and compare flights from Chicago to Calgary that are best for you.

Fly from

Chicago

Fly to

Calgary

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 29/5

2:16 p.m.-10:38 p.m.

1 stop9h 22m

Calgary

Thu 29/5

12:55 a.m.-11:24 a.m.

1 stop9h 29m

C$ 229

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 27/5

8:45 a.m.-9:48 p.m.

1 stop14h 03m

Calgary

Tue 3/6

12:38 p.m.-5:10 p.m.

Nonstop3h 32m

C$ 263

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 25/5

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

Calgary

Tue 3/6

12:15 p.m.-4:44 p.m.

Nonstop3h 29m

C$ 267

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 9/5

8:45 a.m.-11:41 a.m.

Nonstop3h 56m

Calgary

Mon 12/5

11:55 p.m.-8:50 a.m.

1 stop7h 55m

C$ 305

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 13/8

1:55 p.m.-11:03 p.m.

1 stop10h 08m

Calgary

Tue 26/8

6:35 a.m.-2:59 p.m.

1 stop7h 24m

C$ 348

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sun 25/5

9:20 a.m.-11:01 p.m.

2 stops14h 41m

Calgary

Tue 27/5

6:30 a.m.-1:15 p.m.

1 stop5h 45m

C$ 362

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 14/8

8:34 p.m.-11:29 p.m.

Nonstop3h 55m

Calgary

Wed 20/8

1:29 p.m.-5:54 p.m.

Nonstop3h 25m

C$ 366

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 13/5

9:34 a.m.-8:05 p.m.

1 stop11h 31m

Calgary

Tue 20/5

5:30 p.m.-1:17 p.m.

1 stop18h 47m

C$ 450

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 28/5

9:40 a.m.-9:15 p.m.

2 stops12h 35m

Calgary

Mon 2/6

11:55 p.m.-4:24 p.m.

1 stop15h 29m

C$ 495

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 26/5

7:10 a.m.-6:21 p.m.

1 stop12h 11m

C$ 107

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/4

Showing 1-10 of 20 results
1
2

Best time to book a flight from Chicago to Calgary

Have a flexible travel schedule? Discover the best time to fly to Calgary from Chicago 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 Chicago to Calgary

How far ahead should I book a flight from Chicago to Calgary?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Calgary. Price data was last updated on 25 April 2025.

Booking 22 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Calgary. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Calgary?

Currently, January is the cheapest month in which you can book a flight from Chicago to Calgary (average of C$ 139). Flying from Chicago to Calgary in July is currently the most expensive (average of C$ 263). 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.

What is the cheapest time of day to fly from CHI to YYC?

Find hourly flight availability from Chicago to Calgary. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 29 April 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 40% on flights from Chicago to Calgary by exploring options for tickets in the afternoon.

Weekly flight availability from Chicago to Calgary

Explore weekly flight availability from Chicago to Calgary. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 29 April 2025.

The most flights from CHI to YYC are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

Rainfall in Calgary by month

Plan your trip to Calgary by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Calgary ranges from 9.0 - 94.0 mm per month. June is typically the wettest month, when rainfall can reach 94.0 mm. January is typically the driest time to visit Calgary when rainfall is around 9.0 mm.

Temperature in Calgary by month

Plan your trip to Calgary by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Calgary, 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 17.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -7.0 C).

Reviews of airlines servicing Calgary

Get insights into the airlines that provide service to Calgary. 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 Calgary. Reviews last updated 29 April 2025.
Read through reviews of airlines operating flights from Chicago to Calgary, such as Alaska Airlines, Porter Airlines and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,949 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Porter Airlines
8.0
Very good
285 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,929 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,949 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Calgary. 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 into for flights to Calgary from Chicago?

    For a flight from Chicago to Calgary, you will be flying into Calgary. Calgary (YYC) is just 9.3 km from the centre of the city. Calgary is the only Calgary airport and it handles 5 inbound flights from Chicago per day. 3 airlines have flights to Calgary from Chicago on a regular basis.

  • What are the cheapest airlines flying from Chicago to Calgary round-trip?

    Our cheapest airline available from Chicago to Calgary is Air Canada. Our recent data shows that you can find tickets from as low as C$ 229 on this airline. Additional options worth looking into are United Airlines and WestJet, starting at C$ 263 and C$ 267 round-trip. Air Canada is currently priced 48% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Chicago to Calgary one-way?

    C$ 107 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on WestJet and Air Canada, with prices starting from C$ 111 and C$ 116, respectively.

  • What are the most reliable airlines from Chicago to Calgary?

    Consider Air Canada (79%), United Airlines (79%) or American Airlines (78%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Calgary.

  • What are the cheapest flights from Chicago to Calgary?

    While on average a flight from Chicago to Calgary is generally C$ 180, our data shows the cheapest flight currently is C$ 95. When looking at the most popular route, (Chicago O'Hare Intl - Calgary), you can expect to pay C$ 251 for that flight.

  • Can I find deals for flights from Chicago to Calgary that include hotel bookings?

    Yes. In addition to deals on Chicago to Calgary flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Calgary?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Calgary.

  • Can I find deals for business class flights from Chicago to Calgary?

    Yes. Cheapflights offers flight deals from Chicago to Calgary 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 Chicago to Calgary?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Calgary (average of C$ 139). Flying from Chicago to Calgary in July is currently the most expensive (average of C$ 263). 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

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Canmore
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Radium Hot Springs
Drumheller
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Alternative routes for Chicago to Calgary

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Calgary flights
O'Hare Intl to Edmonton flights
St. Louis to Calgary flights
St. Louis to Edmonton flights
Moline to Edmonton flights

Top 3 airlines flying from Chicago to Calgary

Discover the top 3 airlines that operate flights from Chicago to Calgary. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 29 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 128AverageC$ 657FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 144AverageC$ 288FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 195AverageC$ 600FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

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

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Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Chicago to Calgary for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Chicago to Calgary with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago to Calgary, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Chicago to Calgary become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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