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Cheap flights from Chicago to Calgary from C$ 69

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 19/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYC
17 Jan — 24 Jan1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Chicago to Calgary are usually found in May or October, booked 23 days in advance, depart on a Wednesday or Tuesday and return on a Friday

Cheap flight deals from Chicago to Calgary

Enter your travel dates to find the best prices.

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 18 December 2025.

Thu 18/121:35 p.m.ORD - YYC
1 stop10h 38mDelta
Wed 24/127:30 a.m.YYC - ORD
2 stops15h 32mDelta
Deal found 17/12C$ 584
Tue 23/1211:48 a.m.MDW - YYC
1 stop10h 18mDelta
Thu 8/16:30 a.m.YYC - MDW
1 stop5h 39mDelta
Deal found 16/12C$ 586
Thu 18/121:50 p.m.MDW - YYC
1 stop8h 07mDelta
Wed 24/126:30 a.m.YYC - MDW
1 stop9h 49mDelta
Deal found 17/12C$ 682
Fri 19/121:35 p.m.ORD - YYC
1 stop10h 38mDelta
Wed 24/127:30 a.m.YYC - ORD
2 stops15h 32mDelta
Deal found 17/12C$ 704
Tue 23/128:30 p.m.ORD - YYC
1 stop13h 13mMultiple Airlines
Thu 8/112:37 p.m.YYC - ORD
Nonstop3h 31mMultiple Airlines
Deal found 16/12C$ 729
Tue 23/121:59 p.m.ORD - YYC
1 stop10h 16mDelta
Thu 8/16:30 a.m.YYC - ORD
2 stops13h 35mDelta
Deal found 16/12C$ 737
Tue 23/128:30 p.m.ORD - YYC
1 stop13h 13mAir Canada
Thu 8/18:25 a.m.YYC - ORD
2 stops10h 20mAir Canada
Deal found 16/12C$ 778
Thu 18/121:14 p.m.MDW - YYC
2 stops8h 43mDelta
Thu 25/126:30 a.m.YYC - MDW
1 stop9h 49mDelta
Deal found 17/12C$ 823
Sat 20/121:59 p.m.ORD - YYC
1 stop10h 16mDelta
Tue 23/126:30 a.m.YYC - ORD
1 stop10h 17mDelta
Deal found 16/12C$ 823
Sat 20/121:59 p.m.ORD - YYC
1 stop10h 16mDelta
Mon 22/126:30 a.m.YYC - ORD
1 stop10h 17mDelta
Deal found 17/12C$ 836
Wed 24/1211:48 a.m.MDW - YYC
1 stop10h 18mDelta
Thu 1/16:30 a.m.YYC - MDW
1 stop9h 49mDelta
Deal found 16/12C$ 896
Wed 31/126:00 a.m.MDW - YYC
2 stops18h 15mDelta
Sun 4/17:35 p.m.YYC - MDW
2 stops16h 13mDelta
Deal found 17/12C$ 904

Find 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 18 December 2025.

Round-trip from

C$ 219

One-way from

C$ 69

Popular in

December

Cheapest in

May

Average price

C$ 558

Good round-trip deal

C$ 215 or less

Good one-way deal

C$ 121 or less
WestJet
  • WestJet
  • 17/5-2/6
  • Nonstop
  • 7h 17m total
  • Chicago to Calgary
Search Deals
WestJet
  • WestJet
  • 19/1
  • Nonstop
  • 3h 55m total
  • Chicago to Calgary
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Calgary.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Calgary.
Search Deals

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 18 December 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

Sat 16/5

9:45 p.m.-1:56 p.m.

1 stop17h 11m

Calgary

Sat 23/5

8:30 a.m.-12:50 p.m.

Nonstop3h 20m

C$ 255

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 3/2

5:40 a.m.-1:08 p.m.

1 stop8h 28m

Calgary

Wed 11/2

6:15 a.m.-11:59 p.m.

1 stop16h 44m

C$ 269

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 11/5

7:41 a.m.-6:15 p.m.

1 stop11h 34m

Calgary

Tue 19/5

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

Nonstop3h 28m

C$ 311

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 12/5

7:41 a.m.-6:15 p.m.

1 stop11h 34m

Calgary

Sun 17/5

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

Nonstop3h 28m

C$ 313

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 9/5

7:41 a.m.-6:15 p.m.

1 stop11h 34m

Calgary

Thu 14/5

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

Nonstop3h 28m

C$ 316

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 9/5

7:41 a.m.-6:15 p.m.

1 stop11h 34m

Calgary

Mon 18/5

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

Nonstop3h 28m

C$ 316

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 9/5

7:41 a.m.-6:15 p.m.

1 stop11h 34m

Calgary

Sun 17/5

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

Nonstop3h 28m

C$ 316

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 13/5

7:41 a.m.-6:15 p.m.

1 stop11h 34m

Calgary

Mon 18/5

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

Nonstop3h 28m

C$ 316

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 13/5

7:41 a.m.-6:15 p.m.

1 stop11h 34m

Calgary

Sun 17/5

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

Nonstop3h 28m

C$ 316

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 7/5

7:41 a.m.-6:15 p.m.

1 stop11h 34m

Calgary

Mon 18/5

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

Nonstop3h 28m

C$ 329

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/12

Showing 1-10 of 37 results
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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 12 December 2025.

Booking 23 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, April is the cheapest month in which you can book a flight from Chicago to Calgary (average of C$ 110). Flying from Chicago to Calgary in December is currently the most expensive (average of C$ 222). 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 18 December 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 38% 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 18 December 2025.

The most flights from CHI to YYC are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

How often are flights from Chicago to Calgary delayed?

About 27% of weekly flights between Chicago and Calgary have experienced delays in the past year, with the average delay time being 143 minutes.

What is the most punctual flight time for Chicago to Calgary flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Calgary flights?

Over the past year, United Airlines has had the lowest number of delays on this route, with just 21% of flights being delayed.

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 18 December 2025.
Get a feel of what it's like to fly with WestJet 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.
WestJet
7.2
Good
3,204 reviews
Check prices

Overall

7.2

Entertainment

6.1

Comfort

7.1

Food

6.2

Crew

7.9

Boarding

7.4

Reviews

1 / 20
6.0
Good

Anne,Dec 2025

HUX - YYC

Travel on airplanes sucks now. My legs are cramped because i cant stretch them out, if i drop anything theres not enough room to bend and reach to pick it up, the trays if down crowd my middle, the pocket on the seat in front is so small i cant even put my water bottle in it, because the seats are so close, the recline function is pretty irrelevant, but the staff are great and doing their best.
WestJet
7.2
Good
3,204 reviews
WestJet
7.2
Good
3,204 reviews
Check prices

Overall

7.2

Entertainment

6.1

Comfort

7.1

Food

6.2

Crew

7.9

Boarding

7.4

Reviews

1 / 20
6.0
Good

Anne,Dec 2025

HUX - YYC

Travel on airplanes sucks now. My legs are cramped because i cant stretch them out, if i drop anything theres not enough room to bend and reach to pick it up, the trays if down crowd my middle, the pocket on the seat in front is so small i cant even put my water bottle in it, because the seats are so close, the recline function is pretty irrelevant, but the staff are great and doing their best.

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 2 inbound flights from Chicago per day. 1 airline has flights to Calgary from Chicago on a regular basis.

  • How long is the flight from Chicago to Calgary?

    A quick flight from Chicago to Calgary can take about 12h 17m. United Airlines provides one of the quickest options available for as low as C$ 360. The distance from Chicago to Calgary is about 2247 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What is the cheapest airline to fly 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$ 159 on this airline. WestJet is currently priced 59% below the average price you’ll pay for this route.

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

    C$ 78 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on Air Canada and United Airlines, with prices starting from C$ 87 and C$ 87, respectively.

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

    Consider American Airlines (81%), Qatar Airways (81%) or British Airways (81%) 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$ 189, our data shows the cheapest flight currently is C$ 84. When looking at the most popular route, (Chicago O'Hare Intl - Calgary), you can expect to pay C$ 226 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, April is the cheapest month in which you can book a flight from Chicago to Calgary (average of C$ 110). Flying from Chicago to Calgary in December is currently the most expensive (average of C$ 222). 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
Radium Hot Springs
Airdrie
Kananaskis
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
St. Louis to Calgary flights
O'Hare Intl to Edmonton flights
St. Louis to Edmonton flights
Moline to Edmonton flights

Top airline flying from Chicago to Calgary

Discover the top airline 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 18 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 211AverageC$ 392FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Calgary from Chicago today with Cheapflights!

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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