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Cheap flights from Chicago to Calgary from C$ 98

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 26/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYC
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

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

Find 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 30 October 2025.

Fri 5/122:20 p.m.ORD - YYC
Nonstop3h 55mWestJet
Mon 8/129:00 a.m.YYC - ORD
Nonstop3h 35mWestJet
Deal found 29/10C$ 276
Sat 13/121:24 p.m.ORD - YYC
2 stops26h 46mMultiple Airlines
Fri 9/19:00 a.m.YYC - ORD
Nonstop3h 35mMultiple Airlines
Deal found 28/10C$ 283
Mon 15/128:45 a.m.ORD - YYC
Nonstop3h 50mLufthansa
Wed 24/1212:37 p.m.YYC - ORD
Nonstop3h 31mLufthansa
Deal found 29/10C$ 288
Wed 10/128:45 a.m.ORD - YYC
Nonstop3h 50mUnited Airlines
Sat 13/1212:37 p.m.YYC - ORD
Nonstop3h 33mUnited Airlines
Deal found 30/10C$ 300
Sun 9/118:45 a.m.ORD - YYC
Nonstop3h 50mUnited Airlines
Wed 12/1112:37 p.m.YYC - ORD
Nonstop3h 33mUnited Airlines
Deal found 30/10C$ 303
Sat 6/126:11 a.m.ORD - YYC
1 stop13h 58mMultiple Airlines
Tue 9/128:55 a.m.YYC - ORD
1 stop8h 51mMultiple Airlines
Deal found 27/10C$ 306
Fri 7/112:20 p.m.ORD - YYC
Nonstop3h 55mMultiple Airlines
Mon 10/1112:30 a.m.YYC - ORD
1 stop9h 44mMultiple Airlines
Deal found 29/10C$ 314
Mon 8/122:20 p.m.ORD - YYC
Nonstop3h 55mMultiple Airlines
Wed 10/128:55 a.m.YYC - ORD
1 stop8h 51mMultiple Airlines
Deal found 29/10C$ 316
Mon 15/128:42 p.m.MDW - YYC
1 stop16h 02mMultiple Airlines
Wed 24/129:45 p.m.YYC - MDW
2 stops18h 53mMultiple Airlines
Deal found 29/10C$ 341
Wed 10/121:50 p.m.MDW - YYC
1 stop8h 07mDelta
Sat 13/126:35 a.m.YYC - MDW
1 stop5h 35mDelta
Deal found 29/10C$ 350
Thu 6/116:30 a.m.MDW - YYC
1 stop11h 36mMultiple Airlines
Mon 10/1112:30 a.m.YYC - MDW
1 stop10h 08mMultiple Airlines
Deal found 29/10C$ 376
Thu 27/116:05 a.m.MDW - YYC
1 stop14h 04mMultiple Airlines
Thu 4/127:30 a.m.YYC - MDW
2 stops13h 42mMultiple Airlines
Deal found 28/10C$ 383

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 30 October 2025.

Round-trip from

C$ 242

One-way from

C$ 98

Popular in

December

Cheapest in

October

Average price

C$ 297

Good round-trip deal

C$ 266 or less

Good one-way deal

C$ 165 or less
WestJet
  • WestJet
  • 2/2-6/2
  • Nonstop
  • 7h 30m total
  • Chicago to Calgary
Search Deals
WestJet
  • WestJet
  • 26/4
  • Nonstop
  • 3h 49m total
  • Chicago to Calgary
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 135 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 47 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 30 October 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 2/3

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

Calgary

Wed 11/3

12:30 p.m.-4:50 p.m.

Nonstop3h 20m

C$ 297

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 9/11

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

Calgary

Wed 12/11

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

C$ 303

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 2/12

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

Calgary

Sat 6/12

5:35 a.m.-2:55 p.m.

1 stop8h 20m

C$ 311

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 16/12

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

Calgary

Wed 17/12

5:35 a.m.-3:10 p.m.

1 stop8h 35m

C$ 318

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 3/3

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

Calgary

Wed 11/3

6:20 a.m.-5:00 p.m.

1 stop9h 40m

C$ 318

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 6/1

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

Calgary

Thu 8/1

12:37 p.m.-5:08 p.m.

Nonstop3h 31m

C$ 328

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 2/12

1:50 p.m.-8:57 p.m.

1 stop8h 07m

Calgary

Sat 6/12

6:35 a.m.-1:10 p.m.

1 stop5h 35m

C$ 350

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 10/12

1:50 p.m.-8:57 p.m.

1 stop8h 07m

Calgary

Sat 13/12

6:35 a.m.-1:10 p.m.

1 stop5h 35m

C$ 350

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 6/1

1:49 p.m.-8:56 p.m.

1 stop8h 07m

Calgary

Wed 14/1

6:30 a.m.-1:09 p.m.

1 stop5h 39m

C$ 350

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 17/11

6:00 a.m.-1:53 p.m.

1 stop8h 53m

Calgary

Mon 24/11

6:35 a.m.-4:52 p.m.

1 stop9h 17m

C$ 350

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/10

Showing 1-10 of 40 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 24 October 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$ 112). Flying from Chicago to Calgary in December is currently the most expensive (average of C$ 225). 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 30 October 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.

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.

Ottawa (YOW) – chosen by Cheapflights users on 50% 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$ 323.

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 Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 7h 50m.

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 30 October 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
3,152 reviews
Check prices

Overall

7.2

Boarding

7.4

Comfort

7.1

Crew

7.9

Food

6.2

Entertainment

6.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Oct 2025

PVR - YYC

Both departure flight and return flight were delayed causing a missed connection due to crew not showing up. Had to spend an extra 2 nights in hotels as a result. Westjet said they would provide food vouchers but we only received half the amount they said we would and then they didn’t even work. All in all flying with west jet caused me over $1500 in damages. Dealing with customer support has thus far been futile.
WestJet
7.2
Good
3,152 reviews
WestJet
7.2
Good
3,152 reviews
Check prices

Overall

7.2

Boarding

7.4

Comfort

7.1

Crew

7.9

Food

6.2

Entertainment

6.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Oct 2025

PVR - YYC

Both departure flight and return flight were delayed causing a missed connection due to crew not showing up. Had to spend an extra 2 nights in hotels as a result. Westjet said they would provide food vouchers but we only received half the amount they said we would and then they didn’t even work. All in all flying with west jet caused me over $1500 in damages. Dealing with customer support has thus far been futile.

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 3h 50m. United Airlines provides one of the quickest options available for as low as C$ 297. The distance from Chicago to Calgary is about 2223 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$ 213 on this airline. 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$ 117 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from C$ 117 and C$ 140, respectively.

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

    Consider Air Canada (74%), United Airlines (74%) or British Airways (73%) 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$ 248, our data shows the cheapest flight currently is C$ 123. When looking at the most popular route, (Chicago O'Hare Intl - Calgary), you can expect to pay C$ 260 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$ 112). Flying from Chicago to Calgary in December is currently the most expensive (average of C$ 225). 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
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
O'Hare Intl to Edmonton flights
St. Louis to Calgary 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 30 October 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 213AverageC$ 351FlexibilityNo cancel feeOn-time60%
Search WestJet 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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