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Cheap flights from Chicago to Calgary from C$ 100

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 26/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYC
3 Aug — 10 Aug1
1 adult

Cheapflights Tip: The best prices from Chicago to Calgary are usually found in May or October, booked 35 days in advance, depart on a Wednesday or Tuesday and return on a Friday

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 July 2025.

Round-trip from

C$ 214

One-way from

C$ 100

Popular in

December

Cheapest in

May

Average price

C$ 462

Good round-trip deal

C$ 250 or less

Good one-way deal

C$ 138 or less
WestJet
  • WestJet
  • 15/9-24/9
  • Nonstop
  • 7h 17m total
  • Chicago to Calgary
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WestJet
  • WestJet
  • 26/9
  • Nonstop
  • 3h 49m total
  • Chicago to Calgary
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Highest demand for flights based on searches. 21% potential increase in price (C$ 156 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease (C$ 51 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 2025.

Mon 15/95:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Wed 24/912:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 29/7C$ 214
Mon 15/93:50 p.m.ORD - YYC
1 stop8h 32mMultiple Airlines
Wed 24/912:15 p.m.YYC - ORD
Nonstop3h 28mMultiple Airlines
Deal found 29/7C$ 217
Mon 15/96:20 p.m.ORD - YYC
1 stop7h 52mAir Canada
Tue 23/91:10 a.m.YYC - ORD
1 stop7h 41mAir Canada
Deal found 29/7C$ 220
Tue 14/108:47 a.m.ORD - YYC
Nonstop3h 51mUnited Airlines
Fri 17/1012:38 p.m.YYC - ORD
Nonstop3h 32mUnited Airlines
Deal found 29/7C$ 259
Sat 27/91:43 p.m.MDW - YYC
1 stop7h 59mDelta
Sat 4/106:40 a.m.YYC - MDW
1 stop9h 55mDelta
Deal found 29/7C$ 346
Wed 17/99:00 a.m.MDW - YYC
1 stop12h 00mMultiple Airlines
Mon 22/912:30 a.m.YYC - MDW
1 stop14h 28mMultiple Airlines
Deal found 26/7C$ 391

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 July 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

Mon 15/9

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

Nonstop3h 49m

Calgary

Wed 24/9

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

C$ 214

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 15/9

3:50 p.m.-11:22 p.m.

1 stop8h 32m

Calgary

Wed 24/9

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

C$ 217

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 15/9

6:20 p.m.-1:12 a.m.

1 stop7h 52m

Calgary

Tue 23/9

1:10 a.m.-9:51 a.m.

1 stop7h 41m

C$ 220

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 14/10

8:47 a.m.-11:38 a.m.

Nonstop3h 51m

Calgary

Fri 17/10

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

Nonstop3h 32m

C$ 259

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 27/9

1:43 p.m.-8:42 p.m.

1 stop7h 59m

Calgary

Sat 4/10

6:40 a.m.-5:35 p.m.

1 stop9h 55m

C$ 346

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 17/9

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

1 stop12h 00m

Calgary

Mon 22/9

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

1 stop14h 28m

C$ 391

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 26/9

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

Nonstop3h 49m

C$ 100

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 15/9

8:30 p.m.-11:19 p.m.

Nonstop3h 49m

C$ 103

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 16/9

3:35 p.m.-11:16 p.m.

1 stop8h 41m

C$ 110

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 9/9

8:08 p.m.-10:53 p.m.

Nonstop3h 45m

C$ 112

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/7

Showing 1-10 of 16 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 July 2025.

Booking 35 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 July 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 46% on flights from Chicago to Calgary by exploring options for tickets in the evening.

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 July 2025.

The most flights from CHI to YYC are scheduled on a Monday (15 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (7 on average).

How much does it cost to fly round-trip from Chicago to Calgary?

What’s the top layover airport for flights from Chicago to Calgary?

Share of one-stop round-trip flights from Chicago to Calgary chosen by Cheapflights users in the past 12 months, using the same layover each way.

Toronto (YYZ) – chosen by Cheapflights users on 67% of one-stop itineraries from Chicago to Calgary on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Calgary?

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

Ottawa (YOW) is the most affordable 1-stop option, with an average round-trip price of C$ 317.

What’s the fastest layover option from Chicago to Calgary?

Shortest average travel time for 1-stop one-way flights from Chicago to Calgary, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Ottawa (YOW) have the shortest average one-way travel time for 1-stop routes: 5h 48m.

Which airport typically offers the quickest layover for flights from Chicago to Calgary?

Average layover duration for 1-stop one-way flights from Chicago to Calgary, 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 22m.

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 July 2025.
Get a feel of what it's like to fly with Porter Airlines,Delta, andUnited Airlines from Chicago to Calgary by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
317 reviews
Check prices

Overall

8.0

Comfort

8.0

Crew

8.7

Food

7.6

Entertainment

7.0

Boarding

8.2

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

Overall

8.0

Comfort

8.0

Crew

8.7

Food

7.6

Entertainment

7.0

Boarding

8.2

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
7,979 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Overall

8.0

Comfort

8.0

Crew

8.7

Food

7.6

Entertainment

7.0

Boarding

8.2

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
United Airlines
7.4
Good
8,896 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Overall

8.0

Comfort

8.0

Crew

8.7

Food

7.6

Entertainment

7.0

Boarding

8.2

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
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Overall

8.0

Comfort

8.0

Crew

8.7

Food

7.6

Entertainment

7.0

Boarding

8.2

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
2,972 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Overall

8.0

Comfort

8.0

Crew

8.7

Food

7.6

Entertainment

7.0

Boarding

8.2

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 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 11 inbound flights from Chicago per day. 2 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 WestJet. Our recent data shows that you can find tickets from as low as C$ 214 on this airline. Additional options worth looking into are Air Canada and United Airlines, starting at C$ 220 and C$ 259 round-trip. WestJet is currently priced 49% below the average price you’ll pay for this route.

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

    C$ 100 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on American Airlines and Air Canada, with prices starting from C$ 103 and C$ 110, respectively.

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

    Consider Envoy Air (80%), Air Canada (68%) or United Airlines (68%) 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$ 314, our data shows the cheapest flight currently is C$ 87. When looking at the most popular route, (Chicago O'Hare Intl - Calgary), you can expect to pay C$ 237 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 Calgary?

Book flights to Calgary if you plan to visit one of these locations
Canmore
Airdrie
Radium Hot Springs
Drumheller
Kananaskis

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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
St. Louis to Calgary flights
O'Hare Intl to Edmonton flights
St. Louis to Edmonton flights
Moline to Edmonton flights

Top 2 airlines flying from Chicago to Calgary

Discover the top 2 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 July 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 210AverageC$ 390FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 262AverageC$ 433FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

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

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Why should you use Cheapflights to find cheap flight tickets from Chicago to Calgary?

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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