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Cheap flights from Chicago to Calgary from C$ 139

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 27/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYC
21 Apr — 28 Apr1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Chicago to Calgary are usually found in January or October, booked 23 days in advance, depart on a Thursday or Wednesday 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 22 March 2026.

Wed 27/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Sat 30/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 21/3C$ 307
Sat 2/53:50 p.m.
ORD
-
YYC
1 stop8h 08m
Air Canada
Fri 8/512:50 a.m.
YYC
-
ORD
1 stop8h 28m
Air Canada
Deal found 18/3C$ 329
Tue 5/59:55 a.m.
ORD
-
YYC
1 stop9h 48m
Air Canada
Mon 11/512:50 a.m.
YYC
-
ORD
1 stop8h 28m
Air Canada
Deal found 21/3C$ 333
Sat 18/42:00 p.m.
ORD
-
YYC
1 stop7h 28m
Air Canada
Sat 25/45:45 a.m.
YYC
-
ORD
1 stop8h 30m
Air Canada
Deal found 19/3C$ 343
Sat 18/42:00 p.m.
ORD
-
YYC
1 stop7h 28m
Air Canada
Fri 24/45:45 a.m.
YYC
-
ORD
1 stop8h 30m
Air Canada
Deal found 19/3C$ 348
Mon 25/57:42 p.m.
ORD
-
YYC
Nonstop3h 55m
United Airlines
Fri 29/58:30 a.m.
YYC
-
ORD
Nonstop3h 37m
United Airlines
Deal found 17/3C$ 364
Tue 28/48:42 a.m.
ORD
-
YYC
Nonstop3h 50m
United Airlines
Thu 7/512:34 p.m.
YYC
-
ORD
Nonstop3h 27m
United Airlines
Deal found 19/3C$ 368
Sat 18/48:42 a.m.
ORD
-
YYC
Nonstop3h 50m
United Airlines
Fri 24/412:34 p.m.
YYC
-
ORD
Nonstop3h 27m
United Airlines
Deal found 19/3C$ 373
Wed 27/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Tue 2/612:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 19/3C$ 375
Wed 22/49:29 a.m.
MDW
-
YYC
2 stops14h 31m
Delta
Tue 28/46:40 a.m.
YYC
-
MDW
1 stop5h 52m
Delta
Deal found 19/3C$ 416
Wed 22/49:29 a.m.
MDW
-
YYC
2 stops14h 31m
Delta
Sat 25/46:40 a.m.
YYC
-
MDW
1 stop5h 52m
Delta
Deal found 19/3C$ 421
Sat 6/69:23 a.m.
MDW
-
YYC
2 stops14h 34m
Delta
Tue 23/66:35 a.m.
YYC
-
MDW
1 stop5h 36m
Delta
Deal found 18/3C$ 432

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 22 March 2026.

Round-trip from

C$ 307

One-way from

C$ 139

Popular in

December

Cheapest in

January

Average price

C$ 477

Good round-trip deal

C$ 182 or less

Good one-way deal

C$ 161 or less
WestJet
  • WestJet
  • 27/5-30/5
  • Nonstop
  • 7h 35m total
  • Chicago to Calgary
Search Deals
WestJet
  • WestJet
  • 27/5
  • Nonstop
  • 3h 55m total
  • Chicago to Calgary
Search Deals
High demand for flights, 4% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 22 March 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
Quickest round-trip

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 18/4

8:42 a.m.-11:32 a.m.

Nonstop3h 50m

Calgary

Fri 24/4

12:34 p.m.-5:01 p.m.

Nonstop3h 27m

C$ 373

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 20/4

12:14 p.m.-11:00 p.m.

2 stops11h 46m

Calgary

Wed 29/4

7:40 a.m.-9:38 p.m.

2 stops12h 58m

C$ 449

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 25/7

6:00 a.m.-9:48 p.m.

1 stop16h 48m

Calgary

Sat 1/8

7:15 p.m.-9:42 a.m.

1 stop13h 27m

C$ 466

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 12/8

1:55 p.m.-11:06 p.m.

1 stop10h 11m

Calgary

Wed 19/8

6:35 a.m.-4:48 p.m.

1 stop9h 13m

C$ 466

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 21/7

1:18 p.m.-9:48 p.m.

1 stop9h 30m

Calgary

Tue 28/7

6:00 a.m.-10:49 p.m.

1 stop15h 49m

C$ 466

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 18/7

5:00 a.m.-6:13 p.m.

1 stop14h 13m

Calgary

Sat 25/7

6:00 a.m.-8:25 p.m.

1 stop13h 25m

C$ 466

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sun 19/4

9:29 a.m.-11:00 p.m.

2 stops14h 31m

Calgary

Tue 28/4

6:40 a.m.-1:32 p.m.

1 stop5h 52m

C$ 476

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 10/6

1:55 p.m.-11:06 p.m.

1 stop10h 11m

Calgary

Sun 14/6

6:35 a.m.-4:48 p.m.

1 stop9h 13m

C$ 477

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 14/9

1:55 p.m.-11:06 p.m.

1 stop10h 11m

Calgary

Mon 21/9

6:35 a.m.-4:48 p.m.

1 stop9h 13m

C$ 495

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 2/5

2:12 p.m.-8:40 p.m.

1 stop7h 28m

Calgary

Sat 9/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

C$ 531

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/3

Showing 1-10 of 44 resultsSorted by cheapest first
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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 13 March 2026.

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$ 108). Flying from Chicago to Calgary in December is currently the most expensive (average of C$ 221). 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 22 March 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 37% 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 22 March 2026.

The most flights from CHI to YYC are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 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 30% 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, American Airlines has had the lowest number of delays on this route, with just 26% 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 22 March 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
9,455 reviews
Check prices

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,455 reviews
United Airlines
7.4
Good
9,455 reviews
Check prices

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
WestJet
7.2
Good
3,300 reviews
United Airlines
7.4
Good
9,455 reviews
Check prices

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 3 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$ 373. 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$ 221 on this airline. WestJet is currently priced 45% 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 United Airlines and American Airlines, with prices starting from C$ 87 and C$ 182, respectively.

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

    Consider Air Canada (62%), United Airlines (62%) or American Airlines (54%) 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$ 240, our data shows the cheapest flight currently is C$ 85. When looking at the most popular route, (Chicago O'Hare Intl - Calgary), you can expect to pay C$ 364 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$ 108). Flying from Chicago to Calgary in December is currently the most expensive (average of C$ 221). 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 22 March 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 221AverageC$ 390FlexibilityNo 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!

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