This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 27/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYC
31 Oct — 7 Nov1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Chicago to Calgary are usually found in January or February, booked 64 days in advance, depart on a Monday or Sunday and return on a Friday
Cheap flight deals from Chicago to Calgary
Enter your travel dates to find the best prices.
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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 1 October 2026.
Wed 2/129:00 a.m. -
1 stop12h 37m
Sun 6/128:07 a.m. -
1 stop8h 42m
Deal found 27/9C$ 392
Tue 8/126:00 a.m. -
1 stop16h 37m
Fri 11/129:07 a.m. -
1 stop7h 42m
Deal found 29/9C$ 429
Thu 15/105:30 p.m. -
Nonstop3h 55m
Thu 22/1012:00 p.m. -
Nonstop3h 40m
Deal found 27/9C$ 433
Thu 22/105:30 p.m. -
Nonstop3h 55m
Wed 28/106:00 a.m. -
1 stop8h 38m
Deal found 26/9C$ 440
Thu 15/105:30 p.m. -
Nonstop3h 55m
Tue 20/107:00 p.m. -
1 stop9h 40m
Deal found 27/9C$ 443
Sun 29/118:40 a.m. -
Nonstop4h 55m
Thu 3/121:37 p.m. -
Nonstop2h 33m
Deal found 27/9C$ 454
Fri 11/129:00 a.m. -
1 stop13h 37m
Tue 15/128:07 a.m. -
1 stop8h 42m
Deal found 30/9C$ 456
Tue 8/1212:29 p.m. -
1 stop11h 24m
Fri 11/121:37 p.m. -
Nonstop2h 33m
Deal found 29/9C$ 467
Fri 27/118:40 a.m. -
Nonstop4h 55m
Fri 4/127:00 a.m. -
1 stop7h 38m
Deal found 27/9C$ 473
Best flights from Chicago to Calgary
Discover carefully curated flight deals from Chicago to Calgary that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 1 October 2026.
Tue 8/123:19 p.m. -
1 stop31h 18m
Fri 11/129:07 a.m. -
2 stops27h 03m
Deal found 30/9C$ 504
Sat 7/114:00 p.m. -
1 stop9h 12m
Wed 11/117:25 a.m. -
1 stop9h 40m
Deal found 28/9C$ 511
Thu 17/128:40 a.m. -
1 stop11h 18m
Sun 20/121:37 p.m. -
Nonstop2h 33m
Deal found 27/9C$ 511
Thu 5/118:40 a.m. -
Nonstop4h 55m
Sat 7/116:50 p.m. -
1 stop13h 33m
Deal found 26/9C$ 592
Fri 23/102:03 p.m. -
1 stop10h 07m
Tue 27/107:45 a.m. -
1 stop5h 51m
Deal found 30/9C$ 524
Sat 12/128:40 a.m. -
Nonstop4h 55m
Wed 16/121:37 p.m. -
Nonstop2h 33m
Deal found 30/9C$ 561
Mon 11/11:55 p.m. -
1 stop11h 23m
Sun 17/17:15 a.m. -
2 stops12h 22m
Deal found 30/9C$ 525
Thu 22/108:40 a.m. -
Nonstop3h 48m
Sat 24/1012:25 a.m. -
1 stop7h 58m
Deal found 30/9C$ 613
Thu 24/1210:00 p.m. -
1 stop18h 21m
Tue 29/127:00 a.m. -
1 stop11h 30m
Deal found 28/9C$ 575
Fri 23/108:40 a.m. -
Nonstop3h 48m
Mon 26/106:00 a.m. -
1 stop14h 30m
Deal found 30/9C$ 616
Mon 7/128:40 a.m. -
Nonstop4h 55m
Sun 13/121:37 p.m. -
Nonstop2h 33m
Deal found 28/9C$ 673
Direct flights from Chicago to Calgary
Explore direct flight options from Chicago to Calgary based on user searches, and compare prices and availability for your desired travel dates. Data last updated 1 October 2026.
Thu 15/105:30 p.m. -
Nonstop3h 55m
Thu 22/1012:00 p.m. -
Nonstop3h 40m
Deal found 27/9C$ 433
Sun 29/118:40 a.m. -
Nonstop4h 55m
Wed 2/121:37 p.m. -
Nonstop2h 33m
Deal found 27/9C$ 454
Fri 30/108:40 a.m. -
Nonstop3h 55m
Sat 31/1012:37 p.m. -
Nonstop3h 33m
Deal found 28/9C$ 476
Thu 22/1010:00 a.m. -
Nonstop3h 51m
Sat 31/101:59 p.m. -
Nonstop3h 45m
Deal found 29/9C$ 481
Thu 22/1010:00 a.m. -
Nonstop3h 51m
Thu 29/101:51 p.m. -
Nonstop3h 45m
Deal found 30/9C$ 487
Thu 15/108:40 a.m. -
Nonstop3h 48m
Tue 20/1012:30 p.m. -
Nonstop3h 35m
Deal found 28/9C$ 494
Thu 15/1010:00 a.m. -
Nonstop3h 51m
Tue 20/101:51 p.m. -
Nonstop3h 45m
Deal found 30/9C$ 500
Fri 30/108:40 a.m. -
Nonstop3h 55m
Tue 3/111:37 p.m. -
Nonstop2h 33m
Deal found 28/9C$ 507
Sat 6/29:50 a.m. -
Nonstop5h 04m
Thu 11/21:30 p.m. -
Nonstop2h 40m
Deal found 28/9C$ 540
Fri 23/1010:00 a.m. -
Nonstop3h 51m
Tue 27/101:51 p.m. -
Nonstop3h 45m
Deal found 30/9C$ 547
Sun 14/29:00 a.m. -
Nonstop4h 54m
Wed 24/21:30 p.m. -
Nonstop2h 20m
Deal found 27/9C$ 552
Last-minute flights from Chicago to Calgary
Discover last-minute flight deals from Chicago to Calgary. Data last updated 1 October 2026 and is based on user searches.
Thu 15/105:30 p.m. -
Nonstop3h 55m
Thu 22/1012:00 p.m. -
Nonstop3h 40m
Deal found 27/9C$ 433
Thu 15/105:30 p.m. -
Nonstop3h 55m
Tue 20/107:00 p.m. -
1 stop9h 40m
Deal found 27/9C$ 443
Thu 15/108:40 a.m. -
Nonstop3h 48m
Tue 20/1012:30 p.m. -
Nonstop3h 35m
Deal found 28/9C$ 494
Wed 21/105:00 a.m. -
1 stop7h 59m
Fri 30/101:51 p.m. -
Nonstop3h 45m
Deal found 29/9C$ 496
Thu 22/105:30 p.m. -
Nonstop3h 55m
Wed 28/106:00 a.m. -
1 stop8h 38m
Deal found 26/9C$ 440
Thu 22/1010:00 a.m. -
Nonstop3h 51m
Sat 31/101:59 p.m. -
Nonstop3h 45m
Deal found 29/9C$ 481
Thu 22/1010:00 a.m. -
Nonstop3h 51m
Thu 29/101:51 p.m. -
Nonstop3h 45m
Deal found 30/9C$ 487
Thu 22/102:00 p.m. -
1 stop12h 17m
Wed 28/106:00 a.m. -
1 stop8h 38m
Deal found 29/9C$ 493
Fri 30/108:40 a.m. -
Nonstop3h 55m
Sat 31/1012:37 p.m. -
Nonstop3h 33m
Deal found 28/9C$ 476
One-way flights from Chicago to Calgary
Search for one-way flight options from Chicago to Calgary. Find affordable one-way fares based on user searches. Data last updated 1 October 2026.
Fri 27/118:40 a.m. -
Nonstop4h 55m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 28/9C$ 192
Sat 28/118:40 a.m. -
Nonstop4h 55m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 29/9C$ 200
Tue 20/108:45 a.m. -
1 stop8h 12m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 28/9C$ 202
Wed 28/108:40 a.m. -
Nonstop3h 55m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 28/9C$ 203
Fri 27/113:40 p.m. -
1 stop10h 10m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 28/9C$ 204
Sun 29/116:23 a.m. -
1 stop7h 52m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 28/9C$ 206
Sat 24/108:40 a.m. -
Nonstop3h 48m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 28/9C$ 209
Mon 5/105:46 p.m. -
1 stop17h 57m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 26/9C$ 212
Tue 27/101:55 p.m. -
1 stop10h 55m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 27/9C$ 214
Wed 28/1012:11 p.m. -
1 stop10h 34m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 28/9C$ 216
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 1 October 2026.
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 7,457,451 searches. Data last updated 1 October 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 Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Wed 28/10
8:40 a.m.-11:35 a.m.
Nonstop3h 55m
Calgary
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 203
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Fri 30/10
8:40 a.m.-11:35 a.m.
Nonstop3h 55m
Calgary
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 203
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Sun 29/11
6:23 a.m.-2:15 p.m.
1 stop7h 52m
Calgary
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 206
Quickest round-trip
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Thu 22/10
8:40 a.m.-11:28 a.m.
Nonstop3h 48m
Calgary
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 209
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Tue 1/12
12:34 p.m.-11:07 p.m.
1 stop10h 33m
Calgary
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 217
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Sat 31/10
1:59 p.m.-11:12 p.m.
1 stop10h 13m
Calgary
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 217
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Fri 23/10
6:00 a.m.-9:48 p.m.
1 stop16h 48m
Calgary
Wed 31/12
12:00 a.m.-1:00 a.m.
Nonstop0h 00m
C$ 223
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Tue 8/12
3:19 p.m.-10:37 p.m.
1 stop31h 18m
Calgary
Fri 11/12
9:07 a.m.-12:10 p.m.
2 stops27h 03m
C$ 504
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Sat 7/11
4:00 p.m.-1:12 a.m.
1 stop9h 12m
Calgary
Wed 11/11
7:25 a.m.-5:05 p.m.
1 stop9h 40m
C$ 511
ChicagoCalgary
ORD Chicago O'Hare Intl - YYC Calgary
ORDYYC
Chicago O'Hare Intl
Thu 17/12
8:40 a.m.-7:58 p.m.
1 stop11h 18m
Calgary
Sun 20/12
1:37 p.m.-4:10 p.m.
Nonstop2h 33m
C$ 511
Flights are sorted by cheapest round-trip flights first.
Deals found on 28/9
Showing 1-10 of 18 resultsSorted by cheapest first
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.
CHI-YYC
ORD-YYC
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
CHI-YYC
ORD-YYC
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$ 325). Flying from Chicago to Calgary in July is currently the most expensive (average of C$ 636). 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 1 October 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 50% 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 1 October 2026.
The most flights from CHI to YYC are scheduled on a Monday (11 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Chicago to Calgary?
Airfare is typical for this route at the moment.
Chicago to Calgary flights typically cost between C$ 334 and C$ 650 in December.The cheapest round-trip price found within the last 5 days was C$ 392 on Alaska Airlines (2 Dec-6 Dec).
How often are flights from Chicago to Calgary delayed?
About 26% of weekly flights between Chicago and Calgary have experienced delays in the past year, with the average delay time being 144 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 at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday 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 24% 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 1 October 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.
I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
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 7 inbound flights from Chicago per day. 2 airlines have 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 10h 07m. Alaska Airlines provides one of the quickest options available for as low as C$ 524. 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 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$ 262 on this airline. An additional option worth looking into is United Airlines, starting at C$ 530. WestJet is currently priced 47% below the average price you’ll pay for this route.
What are the cheapest airlines to fly from Chicago to Calgary one-way?
C$ 91 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on WestJet and American Airlines, with prices starting from C$ 123 and C$ 213, respectively.
What are the most reliable airlines from Chicago to Calgary?
Consider Porter Airlines (70%), American Airlines (64%) or United Airlines (58%) 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$ 572, our data shows the cheapest flight currently is C$ 176. When looking at the most popular route, (Chicago O'Hare Intl - Calgary), you can expect to pay C$ 453 for that flight.
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$ 325). Flying from Chicago to Calgary in July is currently the most expensive (average of C$ 636). 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.
Explore flights to Calgary departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 1 October 2026.
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 7,457,451 searches. Data last updated 1 October 2026.
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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