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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
12 Oct — 19 Oct1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Calgary to Chicago are usually found in January or November, booked 26 days in advance, depart on a Friday or Thursday and return on a Monday
Cheap flight deals from Calgary to Chicago
Enter your travel dates to find the best prices.
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Best
Direct
Last-minute
One-way
Cheapest flights from Calgary to Chicago
Explore the most affordable flight options available from Calgary to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 September 2026.
Fri 30/106:00 a.m. -
1 stop16h 59m
Thu 5/118:40 a.m. -
Nonstop4h 55m
Deal found 9/9C$ 351
Mon 19/101:00 a.m. -
1 stop8h 12m
Tue 27/1010:15 a.m. -
1 stop7h 39m
Deal found 7/9C$ 352
Fri 2/106:00 a.m. -
1 stop13h 22m
Sat 10/103:40 p.m. -
1 stop9h 07m
Deal found 7/9C$ 353
Wed 7/106:00 a.m. -
1 stop16h 59m
Sun 11/106:00 a.m. -
1 stop16h 48m
Deal found 11/9C$ 355
Fri 30/1012:37 p.m. -
Nonstop3h 33m
Thu 5/118:40 a.m. -
Nonstop4h 55m
Deal found 11/9C$ 356
Sat 3/109:20 a.m. -
1 stop6h 15m
Tue 6/108:40 a.m. -
Nonstop3h 48m
Deal found 8/9C$ 357
Sun 11/106:00 a.m. -
1 stop16h 59m
Fri 16/102:15 p.m. -
1 stop9h 42m
Deal found 8/9C$ 359
Wed 2/121:37 p.m. -
Nonstop2h 33m
Tue 8/121:55 p.m. -
1 stop11h 55m
Deal found 10/9C$ 360
Sat 3/106:35 a.m. -
2 stops13h 21m
Tue 6/102:03 p.m. -
1 stop10h 07m
Deal found 8/9C$ 363
Thu 29/106:00 a.m. -
1 stop13h 05m
Tue 3/118:40 a.m. -
Nonstop4h 55m
Deal found 10/9C$ 364
Sat 31/106:35 a.m. -
2 stops9h 12m
Wed 4/111:27 p.m. -
2 stops11h 43m
Deal found 9/9C$ 364
Tue 17/111:37 p.m. -
Nonstop2h 33m
Mon 23/114:30 p.m. -
1 stop8h 36m
Deal found 10/9C$ 367
Best flights from Calgary to Chicago
Discover carefully curated flight deals from Calgary to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 12 September 2026.
Sat 14/117:25 a.m. -
2 stops9h 39m
Wed 18/1112:30 p.m. -
2 stops12h 47m
Deal found 8/9C$ 384
Mon 16/117:00 a.m. -
1 stop14h 46m
Thu 19/118:45 a.m. -
1 stop16h 21m
Deal found 8/9C$ 393
Wed 24/21:30 p.m. -
Nonstop2h 20m
Mon 1/39:00 a.m. -
Nonstop4h 54m
Deal found 11/9C$ 395
Tue 22/122:39 p.m. -
Nonstop2h 45m
Sat 26/129:40 a.m. -
Nonstop5h 19m
Deal found 6/9C$ 482
Mon 16/117:00 a.m. -
1 stop12h 05m
Fri 20/111:55 p.m. -
1 stop11h 11m
Deal found 8/9C$ 393
Tue 27/107:45 a.m. -
2 stops13h 48m
Tue 10/1112:30 p.m. -
2 stops12h 47m
Deal found 9/9C$ 466
Tue 27/106:35 a.m. -
2 stops12h 55m
Tue 10/1112:38 p.m. -
2 stops12h 39m
Deal found 9/9C$ 466
Sun 27/96:35 a.m. -
1 stop9h 24m
Wed 30/92:05 p.m. -
1 stop10h 01m
Deal found 11/9C$ 514
Thu 22/107:00 a.m. -
1 stop9h 45m
Wed 28/106:16 a.m. -
1 stop13h 39m
Deal found 6/9C$ 578
Fri 30/107:45 a.m. -
2 stops13h 48m
Thu 5/1112:27 p.m. -
2 stops12h 43m
Deal found 11/9C$ 550
Wed 28/1012:25 a.m. -
1 stop8h 38m
Sun 1/119:29 a.m. -
2 stops13h 11m
Deal found 6/9C$ 672
Mon 19/1011:35 p.m. -
2 stops16h 12m
Fri 23/1012:27 p.m. -
2 stops11h 43m
Deal found 8/9C$ 673
Thu 29/1012:25 a.m. -
1 stop10h 29m
Mon 2/1110:12 a.m. -
2 stops14h 58m
Deal found 10/9C$ 696
Direct flights from Calgary to Chicago
Explore direct flight options from Calgary to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 12 September 2026.
Fri 23/101:51 p.m. -
Nonstop3h 45m
Fri 30/1010:00 a.m. -
Nonstop3h 51m
Deal found 8/9C$ 352
Fri 30/1012:37 p.m. -
Nonstop3h 33m
Thu 5/118:40 a.m. -
Nonstop4h 55m
Deal found 11/9C$ 356
Fri 2/1012:00 p.m. -
Nonstop3h 40m
Fri 9/105:30 p.m. -
Nonstop3h 55m
Deal found 8/9C$ 363
Thu 22/101:51 p.m. -
Nonstop3h 45m
Tue 27/1010:00 a.m. -
Nonstop3h 51m
Deal found 10/9C$ 381
Mon 21/121:37 p.m. -
Nonstop2h 33m
Tue 5/18:40 a.m. -
Nonstop4h 55m
Deal found 8/9C$ 384
Sun 18/1012:00 p.m. -
Nonstop3h 40m
Fri 23/105:30 p.m. -
Nonstop3h 55m
Deal found 7/9C$ 392
Wed 24/21:30 p.m. -
Nonstop2h 20m
Mon 1/39:00 a.m. -
Nonstop4h 54m
Deal found 11/9C$ 395
Thu 29/1012:37 p.m. -
Nonstop3h 33m
Mon 2/118:40 a.m. -
Nonstop4h 55m
Deal found 8/9C$ 403
Sun 18/1012:00 p.m. -
Nonstop3h 40m
Thu 22/105:30 p.m. -
Nonstop3h 55m
Deal found 6/9C$ 416
Thu 26/111:37 p.m. -
Nonstop2h 33m
Mon 30/118:40 a.m. -
Nonstop4h 55m
Deal found 6/9C$ 424
Last-minute flights from Calgary to Chicago
Discover last-minute flight deals from Calgary to Chicago. Data last updated 12 September 2026 and is based on user searches.
Wed 23/97:00 a.m. -
Nonstop3h 29m
Sat 26/91:46 p.m. -
1 stop8h 56m
Deal found 9/9C$ 370
Fri 2/106:00 a.m. -
1 stop13h 22m
Sat 10/103:40 p.m. -
1 stop9h 07m
Deal found 7/9C$ 353
Sat 3/109:20 a.m. -
1 stop6h 15m
Tue 6/108:40 a.m. -
Nonstop3h 48m
Deal found 8/9C$ 357
Sat 3/106:35 a.m. -
2 stops13h 21m
Tue 6/102:03 p.m. -
1 stop10h 07m
Deal found 8/9C$ 363
Wed 7/106:00 a.m. -
1 stop16h 59m
Sun 11/106:00 a.m. -
1 stop16h 48m
Deal found 11/9C$ 355
Sun 11/106:00 a.m. -
1 stop16h 59m
Fri 16/102:15 p.m. -
1 stop9h 42m
Deal found 8/9C$ 359
Sat 17/1012:50 a.m. -
1 stop7h 10m
Thu 22/108:45 a.m. -
1 stop8h 12m
Deal found 6/9C$ 369
Mon 19/101:00 a.m. -
1 stop8h 12m
Tue 27/1010:15 a.m. -
1 stop7h 39m
Deal found 7/9C$ 352
Thu 29/106:00 a.m. -
1 stop13h 05m
Tue 3/118:40 a.m. -
Nonstop4h 55m
Deal found 10/9C$ 364
Fri 30/106:00 a.m. -
1 stop16h 59m
Thu 5/118:40 a.m. -
Nonstop4h 55m
Deal found 9/9C$ 351
Fri 30/1012:37 p.m. -
Nonstop3h 33m
Thu 5/118:40 a.m. -
Nonstop4h 55m
Deal found 11/9C$ 356
Sat 31/106:35 a.m. -
2 stops9h 12m
Wed 4/111:27 p.m. -
2 stops11h 43m
Deal found 9/9C$ 364
One-way flights from Calgary to Chicago
Search for one-way flight options from Calgary to Chicago. Find affordable one-way fares based on user searches. Data last updated 12 September 2026.
Wed 7/106:00 a.m. -
1 stop15h 46m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 11/9C$ 220
Sat 14/118:45 a.m. -
1 stop6h 54m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 9/9C$ 222
Sat 10/109:20 a.m. -
2 stops9h 28m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 10/9C$ 222
Sat 3/1012:50 a.m. -
1 stop7h 10m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 10/9C$ 224
Tue 10/117:00 a.m. -
2 stops11h 52m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 10/9C$ 226
Mon 7/127:10 a.m. -
2 stops28h 59m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 8/9C$ 227
Sat 3/106:35 a.m. -
2 stops10h 47m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 11/9C$ 231
Sat 3/106:35 a.m. -
1 stop9h 24m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 11/9C$ 231
Mon 8/31:20 a.m. -
1 stop6h 48m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 10/9C$ 236
Tue 2/28:45 a.m. -
1 stop7h 05m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 9/9C$ 241
Tue 9/37:15 a.m. -
2 stops11h 19m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 10/9C$ 241
Sun 20/96:00 a.m. -
1 stop15h 00m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 6/9C$ 242
Find flight deals from Calgary to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Chicago (CHI). 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 12 September 2026.
Customize your flight search to find flights from Calgary to Chicago 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 12 September 2026.
Use the filters below to find and compare flights from Calgary to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
Cheapest round-trip
CalgaryChicago
YYC Calgary - MDW Chicago Midway
YYCMDW
Calgary
Sat 3/10
6:35 a.m.-6:22 p.m.
2 stops10h 47m
Chicago Midway
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 231
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 5/3
7:15 a.m.-7:37 p.m.
2 stops12h 22m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 241
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Wed 10/3
7:15 a.m.-7:37 p.m.
2 stops12h 22m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 241
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Wed 4/11
1:37 p.m.-4:10 p.m.
Nonstop2h 33m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 249
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Wed 7/10
6:35 a.m.-6:10 p.m.
1 stop10h 35m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 256
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Sun 4/10
7:00 a.m.-11:29 a.m.
Nonstop3h 29m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 262
Quickest round-trip
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Wed 3/3
1:30 p.m.-3:50 p.m.
Nonstop2h 20m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 263
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 18/9
6:00 a.m.-9:29 p.m.
1 stop14h 29m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 266
CalgaryChicago
YYC Calgary - MDW Chicago Midway
YYCMDW
Calgary
Fri 22/1
8:45 a.m.-9:10 p.m.
2 stops12h 25m
Chicago Midway
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 272
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Sat 19/9
1:27 p.m.-11:59 p.m.
1 stop9h 32m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 277
Flights are sorted by cheapest round-trip flights first.
Deals found on 11/9
Showing 1-10 of 34 resultsSorted by cheapest first
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Best time to book a flight from Calgary to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Calgary with our price prediction graph.
YYC-CHI
YYC-MDW
YYC-ORD
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 Calgary to Chicago
YYC-CHI
YYC-MDW
YYC-ORD
What is the cheapest month to book a flight from Calgary to Chicago?
Currently, January is the cheapest month in which you can book a flight from Calgary to Chicago (average of C$ 331). Flying from Calgary to Chicago in June is currently the most expensive (average of C$ 502). 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 YYC to CHI?
Find hourly flight availability from Calgary to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 12 September 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Calgary to Chicago as you normally would.
Weekly flight availability from Calgary to Chicago
Explore weekly flight availability from Calgary to Chicago. 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 12 September 2026.
The most flights from YYC to CHI are scheduled on a Thursday (16 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (11 on average).
How much does it cost to fly round-trip from Calgary to Chicago?
Airfare is typical for this route at the moment.
Calgary to Chicago flights typically cost between C$ 349 and C$ 518 in October.The cheapest round-trip price found within the last 5 days was C$ 351 on Lufthansa (30 Oct-5 Nov).
What’s the top layover airport for flights from Calgary to Chicago?
Share of one-stop round-trip flights from Calgary to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.
Toronto (YYZ) – chosen by Cheapflights users on 63% of one-stop itineraries from Calgary to Chicago on Cheapflights.
What’s the cheapest layover airport for flights from Calgary to Chicago?
Average round-trip fare for 1-stop flights from Calgary to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of C$ 427.
What’s the fastest layover option from Calgary to Chicago?
Shortest average travel time for 1-stop one-way flights from Calgary to Chicago, 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 19m.
Which airport typically offers the quickest layover for flights from Calgary to Chicago?
Average layover duration for 1-stop one-way flights from Calgary to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Ottawa (YOW) offer the fastest connection on this route, with an average layover time of 1h 59m.
How far ahead should I book a flight from Calgary to Chicago?
To ensure you get the cheapest price possible for a flight from Calgary to Chicago, you should look to book at least 59 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated 12 September 2026.
Read through reviews of airlines operating flights from Calgary to Chicago, such as Delta,United Airlines, andWestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
The flight crew was 30 minutes late to an am flight and then that caused a delay
Related info for your journey
Find useful and relevant information for your journey from Calgary to Chicago. 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 from for flights from Calgary to Chicago?
For a flight from Calgary to Chicago, you will be flying from Calgary. Calgary (YYC) is just 9.3 km from the centre of the city. Calgary is the only Calgary airport and it handles 13 outbound flights to Chicago per day. 5 airlines have flights to Chicago from Calgary on a regular basis.
How long is the flight from Calgary to Chicago?
For as low as C$ 395, Delta can have you in Chicago from Calgary in 2h 20m. The distance between Calgary and Chicago is about 2223 km. Both multi-stop and direct flights can be found to your destination and back.
What are the cheapest airlines flying from Calgary to Chicago round-trip?
According to our current data, Air Canada (C$ 121), Delta (C$ 141), and United Airlines (C$ 187) offers the cheapest pricing from Calgary to Chicago. Users have found that Air Canada is 69% cheaper than the other options available to this destination.
What are the cheapest airlines to fly from Calgary to Chicago one-way?
To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at C$ 144. Air Canada flights start at C$ 150 while deals on American Airlines start at C$ 168 one-way.
What are the most reliable airlines from Calgary to Chicago?
Before booking your flight to Chicago from Calgary, check out the most reliable airlines to get you to your destination on time: Avianca (85%), Porter Airlines (83%), Qatar Airways( 83%).
What are the cheapest flights from Calgary to Chicago?
The cheapest flight price from Calgary to Chicago is C$ 286. On average you can expect to pay C$ 1,695. The most popular route, (Calgary - Chicago O'Hare Intl), can usually be booked for C$ 319.
Can I find deals for business class flights from Calgary to Chicago?
Yes. Cheapflights offers flight deals from Calgary to Chicago 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 Calgary to Chicago?
Currently, January is the cheapest month in which you can book a flight from Calgary to Chicago (average of C$ 331). Flying from Calgary to Chicago in June is currently the most expensive (average of C$ 502). 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 Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 12 September 2026.
Browse through other flights departing from Calgary. Flights are based on user searches made on Cheapflights and were last updated on 12 September 2026.
Discover the top 5 airlines that operate flights from Calgary to Chicago. 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 12 September 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 Calgary to Chicago?
Cheapflights helps you search for flights from Calgary to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
Why should you use Cheapflights to find cheap flight tickets from Calgary to Chicago?
Cheapflights helps you find that perfect flight to Chicago from Calgary by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!
Can Cheapflights find flights from Calgary to Chicago with no change fees?
Cheapflights does show flights with no change fees to all users. To see these options for flights from Calgary to Chicago, users can toggle the no change fees filter when performing a flight search.
Can Cheapflights notify me if prices for flights from Calgary to Chicago become cheaper?
Of course! You can now track prices for flights from Calgary to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.
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