Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Chicago to Calgary from C$ 187

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 14/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYC
20 Jul — 27 Jul1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Chicago to Calgary are usually found in January or October, booked 35 days in advance, depart on a Friday or Monday 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 20 June 2026.

Tue 15/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Fri 16/1012:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 17/6C$ 418
Mon 14/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Fri 18/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 18/6C$ 423
Sun 27/95:35 p.m.
ORD
-
YYC
1 stop8h 42m
Air Canada
Sat 3/106:30 a.m.
YYC
-
ORD
1 stop7h 25m
Air Canada
Deal found 17/6C$ 425
Wed 9/93:45 p.m.
ORD
-
YYC
1 stop8h 12m
Air Canada
Wed 16/96:30 a.m.
YYC
-
ORD
1 stop7h 25m
Air Canada
Deal found 15/6C$ 427
Mon 21/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Mon 28/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 18/6C$ 429
Sun 6/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Thu 10/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 17/6C$ 430
Thu 10/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Mon 14/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 17/6C$ 432
Tue 15/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Thu 17/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 18/6C$ 433
Tue 11/87:45 p.m.
ORD
-
YYC
Nonstop3h 51m
Multiple Airlines
Tue 11/81:00 a.m.
YYC
-
ORD
1 stop8h 16m
Multiple Airlines
Deal found 17/6C$ 435
Sun 6/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Tue 15/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 18/6C$ 436
Fri 11/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Fri 18/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 18/6C$ 437
Sun 6/95:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Sun 13/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 17/6C$ 439

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 20 June 2026.

Round-trip from

C$ 418

One-way from

C$ 187

Popular in

July

Cheapest in

January

Average price

C$ 504

Good round-trip deal

C$ 246 or less

Good one-way deal

C$ 225 or less
WestJet
  • WestJet
  • 15/9-16/10
  • Nonstop
  • 7h 35m total
  • Chicago to Calgary
Search Deals
WestJet
  • WestJet
  • 14/12
  • Nonstop
  • 4h 55m total
  • Chicago to Calgary
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 118 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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 20 June 2026.
Use the filters below to find and compare flights from Chicago to Calgary that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 16/10

8:40 a.m.-11:28 a.m.

Nonstop3h 48m

Calgary

Wed 21/10

7:30 a.m.-4:58 p.m.

1 stop8h 28m

C$ 481

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 11/9

7:45 p.m.-10:36 p.m.

Nonstop3h 51m

Calgary

Sun 20/9

6:30 a.m.-2:55 p.m.

1 stop7h 25m

C$ 483

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 6/9

7:45 p.m.-10:36 p.m.

Nonstop3h 51m

Calgary

Thu 10/9

12:55 a.m.-9:00 a.m.

1 stop7h 05m

C$ 483

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 29/9

8:40 a.m.-11:28 a.m.

Nonstop3h 48m

Calgary

Thu 1/10

6:00 a.m.-11:59 p.m.

1 stop16h 59m

C$ 484

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 8/9

2:05 p.m.-11:06 p.m.

1 stop10h 01m

Calgary

Sun 13/9

7:15 a.m.-6:01 p.m.

1 stop9h 46m

C$ 525

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 30/6

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

1 stop8h 53m

Calgary

Fri 3/7

6:00 a.m.-6:46 p.m.

1 stop11h 46m

C$ 545

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 8/9

2:00 p.m.-8:42 p.m.

1 stop7h 42m

Calgary

Sun 13/9

6:35 a.m.-1:11 p.m.

1 stop5h 36m

C$ 576

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 13/8

8:28 a.m.-11:04 p.m.

2 stops15h 36m

Calgary

Thu 20/8

7:45 a.m.-6:19 p.m.

1 stop9h 34m

C$ 606

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 29/7

6:30 a.m.-1:14 p.m.

1 stop7h 44m

Calgary

Fri 7/8

6:45 a.m.-4:59 p.m.

1 stop9h 14m

C$ 619

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 19/9

1:14 p.m.-8:15 p.m.

1 stop8h 01m

Calgary

Sat 26/9

7:00 a.m.-6:11 p.m.

2 stops10h 11m

C$ 644

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/6

Showing 1-10 of 39 resultsSorted by cheapest first
1
2
3
4

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

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

Currently, November is the cheapest month in which you can book a flight from Chicago to Calgary (average of C$ 85). Flying from Chicago to Calgary in September is currently the most expensive (average of C$ 875). 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 20 June 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 38% on flights from Chicago to Calgary by exploring options for tickets at noon.

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 20 June 2026.

The most flights from CHI to YYC are scheduled on a Monday (13 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 on average).

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

How often are flights from Chicago to Calgary delayed?

About 31% of weekly flights between Chicago and Calgary have experienced delays in the past year, with the average delay time being 142 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?

Thursday tends to have the lowest number of delays on this route, whereas Friday 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 27% of flights being delayed.

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

Booking 62 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.

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 20 June 2026.
Get a feel of what it's like to fly with United Airlines and 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.
United Airlines
7.4
Good
9,865 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Food

6.6

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,865 reviews
United Airlines
7.4
Good
9,865 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Food

6.6

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
WestJet
7.2
Good
3,375 reviews
United Airlines
7.4
Good
9,865 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Food

6.6

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 12 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 55m. WestJet provides one of the quickest options available for as low as C$ 418. 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$ 261 on this airline. WestJet is currently priced 40% below the average price you’ll pay for this route.

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

    C$ 80 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 American Airlines, with prices starting from C$ 89 and C$ 189, respectively.

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

    Consider Envoy Air (94%), Air Canada (83%) or United Airlines (83%) 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$ 427, our data shows the cheapest flight currently is C$ 147. When looking at the most popular route, (Chicago O'Hare Intl - Calgary), you can expect to pay C$ 419 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, November is the cheapest month in which you can book a flight from Chicago to Calgary (average of C$ 85). Flying from Chicago to Calgary in September is currently the most expensive (average of C$ 875). 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
Kananaskis
Airdrie
Drumheller

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 20 June 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 261AverageC$ 413FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.