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 28/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
26 Nov — 3 Dec1
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 April or February, booked 52 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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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 27 October 2026.
Tue 17/111:45 a.m. -
1 stop9h 22m
Mon 23/113:50 p.m. -
1 stop9h 00m
Deal found 22/10C$ 423
Mon 23/111:45 a.m. -
1 stop9h 22m
Fri 27/113:40 p.m. -
1 stop9h 10m
Deal found 24/10C$ 426
Sat 21/111:45 a.m. -
1 stop9h 22m
Tue 1/1210:05 a.m. -
1 stop7h 53m
Deal found 23/10C$ 429
Mon 7/121:45 a.m. -
1 stop9h 22m
Tue 15/124:30 p.m. -
1 stop7h 36m
Deal found 24/10C$ 433
Wed 25/111:20 a.m. -
1 stop8h 03m
Mon 30/114:30 p.m. -
1 stop7h 36m
Deal found 23/10C$ 436
Fri 4/129:07 a.m. -
1 stop7h 24m
Sun 6/126:00 a.m. -
1 stop15h 37m
Deal found 22/10C$ 439
Fri 4/129:07 a.m. -
1 stop7h 24m
Tue 8/126:00 a.m. -
1 stop15h 37m
Deal found 23/10C$ 440
Thu 10/121:37 p.m. -
Nonstop3h 33m
Thu 17/1212:23 p.m. -
1 stop10h 30m
Deal found 26/10C$ 446
Fri 20/111:20 a.m. -
1 stop8h 03m
Sat 28/113:40 p.m. -
1 stop9h 10m
Deal found 24/10C$ 449
Wed 28/101:51 p.m. -
Nonstop3h 45m
Sat 31/1010:00 a.m. -
Nonstop3h 51m
Deal found 25/10C$ 450
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 27 October 2026.
Fri 4/129:07 a.m. -
2 stops28h 03m
Mon 7/126:00 a.m. -
1 stop15h 37m
Deal found 25/10C$ 477
Wed 18/117:00 a.m. -
1 stop16h 59m
Mon 23/113:50 p.m. -
1 stop9h 00m
Deal found 22/10C$ 489
Thu 19/112:20 p.m. -
2 stops9h 34m
Mon 23/112:03 p.m. -
1 stop10h 14m
Deal found 26/10C$ 505
Sat 21/113:06 p.m. -
1 stop6h 24m
Sat 28/118:40 a.m. -
Nonstop3h 55m
Deal found 24/10C$ 507
Fri 4/121:37 p.m. -
Nonstop3h 33m
Mon 7/123:45 p.m. -
1 stop9h 05m
Deal found 25/10C$ 505
Wed 24/21:39 p.m. -
Nonstop3h 31m
Mon 1/38:40 a.m. -
Nonstop3h 57m
Deal found 26/10C$ 513
Sun 15/117:25 a.m. -
1 stop10h 40m
Sun 22/112:03 p.m. -
1 stop10h 14m
Deal found 22/10C$ 575
Wed 23/127:59 p.m. -
1 stop13h 35m
Tue 29/124:30 p.m. -
1 stop17h 14m
Deal found 26/10C$ 540
Thu 11/21:39 p.m. -
Nonstop3h 31m
Wed 17/28:40 a.m. -
Nonstop3h 57m
Deal found 26/10C$ 597
Thu 11/21:39 p.m. -
Nonstop3h 31m
Fri 19/210:05 a.m. -
1 stop11h 24m
Deal found 26/10C$ 576
Tue 9/210:40 a.m. -
1 stop13h 18m
Wed 17/28:40 a.m. -
Nonstop3h 57m
Deal found 26/10C$ 604
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 27 October 2026.
Mon 23/111:37 p.m. -
Nonstop3h 33m
Tue 1/128:40 a.m. -
Nonstop3h 55m
Deal found 26/10C$ 463
Thu 21/11:37 p.m. -
Nonstop3h 33m
Sun 24/18:40 a.m. -
Nonstop3h 55m
Deal found 27/10C$ 488
Tue 8/121:37 p.m. -
Nonstop3h 33m
Tue 15/128:40 a.m. -
Nonstop3h 55m
Deal found 24/10C$ 491
Fri 4/121:37 p.m. -
Nonstop3h 33m
Tue 8/128:40 a.m. -
Nonstop3h 55m
Deal found 23/10C$ 499
Sat 5/121:37 p.m. -
Nonstop3h 33m
Tue 8/128:40 a.m. -
Nonstop3h 55m
Deal found 23/10C$ 500
Wed 24/21:39 p.m. -
Nonstop3h 31m
Mon 1/38:40 a.m. -
Nonstop3h 57m
Deal found 26/10C$ 513
Wed 24/23:40 p.m. -
Nonstop3h 45m
Mon 1/310:45 a.m. -
Nonstop4h 13m
Deal found 23/10C$ 531
Mon 8/21:37 p.m. -
Nonstop3h 33m
Tue 16/28:40 a.m. -
Nonstop3h 57m
Deal found 25/10C$ 533
Last-minute flights from Calgary to Chicago
Discover last-minute flight deals from Calgary to Chicago. Data last updated 27 October 2026 and is based on user searches.
Wed 28/101:51 p.m. -
Nonstop3h 45m
Sat 31/1010:00 a.m. -
Nonstop3h 51m
Deal found 25/10C$ 450
Fri 30/106:00 a.m. -
1 stop8h 38m
Mon 2/114:30 p.m. -
1 stop7h 51m
Deal found 22/10C$ 439
Sat 31/106:00 a.m. -
1 stop8h 38m
Mon 2/114:30 p.m. -
1 stop7h 51m
Deal found 22/10C$ 454
Mon 16/119:09 a.m. -
2 stops28h 00m
Wed 18/119:30 a.m. -
1 stop12h 09m
Deal found 23/10C$ 453
Tue 17/111:45 a.m. -
1 stop9h 22m
Mon 23/113:50 p.m. -
1 stop9h 00m
Deal found 22/10C$ 423
Fri 20/111:20 a.m. -
1 stop8h 03m
Sat 28/113:40 p.m. -
1 stop9h 10m
Deal found 24/10C$ 449
Sat 21/111:45 a.m. -
1 stop9h 22m
Tue 1/1210:05 a.m. -
1 stop7h 53m
Deal found 23/10C$ 429
Mon 23/111:45 a.m. -
1 stop9h 22m
Fri 27/113:40 p.m. -
1 stop9h 10m
Deal found 24/10C$ 426
Mon 23/111:37 p.m. -
Nonstop3h 33m
Tue 1/128:40 a.m. -
Nonstop3h 55m
Deal found 26/10C$ 463
Wed 25/111:20 a.m. -
1 stop8h 03m
Mon 30/114:30 p.m. -
1 stop7h 36m
Deal found 23/10C$ 436
Wed 25/117:00 a.m. -
1 stop8h 38m
Wed 2/128:45 a.m. -
1 stop9h 13m
Deal found 24/10C$ 456
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 27 October 2026.
Thu 28/19:50 a.m. -
1 stop9h 19m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 23/10C$ 227
Wed 9/128:00 p.m. -
1 stop14h 32m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 27/10C$ 231
Sat 21/117:00 a.m. -
1 stop8h 38m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 22/10C$ 245
Tue 17/111:45 a.m. -
1 stop9h 22m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 22/10C$ 248
Mon 23/111:37 p.m. -
Nonstop3h 33m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 26/10C$ 252
Wed 18/111:20 a.m. -
1 stop8h 03m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 23/10C$ 254
Fri 4/129:07 a.m. -
1 stop8h 42m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 23/10C$ 255
Fri 4/121:45 a.m. -
1 stop9h 22m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 25/10C$ 256
Tue 10/119:09 a.m. -
1 stop8h 28m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 22/10C$ 259
Sun 22/111:45 a.m. -
1 stop9h 22m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 27/10C$ 261
Tue 3/117:00 a.m. -
1 stop8h 38m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 22/10C$ 262
Mon 7/127:00 a.m. -
1 stop8h 38m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 23/10C$ 264
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 27 October 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 27 October 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 - ORD Chicago O'Hare Intl
YYCORD
Calgary
Wed 9/12
9:50 a.m.-1:54 a.m.
2 stops15h 04m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 255
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Tue 9/2
9:00 a.m.-6:59 p.m.
1 stop8h 59m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 266
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 4/12
9:07 a.m.-6:49 p.m.
1 stop8h 42m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 271
Quickest round-trip
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 4/12
1:37 p.m.-6:10 p.m.
Nonstop3h 33m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 275
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Thu 10/12
7:25 a.m.-7:06 p.m.
1 stop10h 41m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 275
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Mon 23/11
1:37 p.m.-6:10 p.m.
Nonstop3h 33m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 275
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Mon 9/11
7:25 a.m.-7:05 p.m.
1 stop10h 40m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 275
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 4/12
1:37 p.m.-6:10 p.m.
Nonstop3h 33m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 278
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Sat 5/12
1:37 p.m.-6:10 p.m.
Nonstop3h 33m
Chicago O'Hare Intl
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 278
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 4/12
9:07 a.m.-2:10 p.m.
2 stops28h 03m
Chicago O'Hare Intl
Mon 7/12
6:00 a.m.-8:37 p.m.
1 stop15h 37m
C$ 477
Flights are sorted by cheapest round-trip flights first.
Deals found on 27/10
Showing 1-10 of 20 resultsSorted by cheapest first
1
2
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-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-ORD
What is the cheapest month to book a flight from Calgary to Chicago?
Currently, May is the cheapest month in which you can book a flight from Calgary to Chicago (average of C$ 364). Flying from Calgary to Chicago in June is currently the most expensive (average of C$ 530). 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 27 October 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 27 October 2026.
The most flights from YYC to CHI are scheduled on a Sunday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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$ 318 and C$ 645 in November.The cheapest round-trip price found within the last 5 days was C$ 423 on Air Canada (17 Nov-23 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 65% 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$ 432.
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 27 October 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 was delayed more then 30 minutes after I hurried and stressed to get to my connecting gate in Atlanta.
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 5 outbound flights to Chicago per day. 6 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$ 463, Alaska Airlines can have you in Chicago from Calgary in 8h 42m. The distance between Calgary and Chicago is about 2223 km.
What are the cheapest airlines flying from Calgary to Chicago round-trip?
According to our current data, Delta (C$ 143), Air Canada (C$ 186), and United Airlines (C$ 189) offers the cheapest pricing from Calgary to Chicago. Users have found that Delta is 68% 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$ 145. Air Canada flights start at C$ 152 while deals on American Airlines start at C$ 170 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: Qatar Airways (82%), Scandinavian Airlines (77%), Air Canada( 75%).
What are the cheapest flights from Calgary to Chicago?
The cheapest flight price from Calgary to Chicago is C$ 261. On average you can expect to pay C$ 1,849. The most popular route, (Calgary - Chicago O'Hare Intl), can usually be booked for C$ 451.
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, May is the cheapest month in which you can book a flight from Calgary to Chicago (average of C$ 364). Flying from Calgary to Chicago in June is currently the most expensive (average of C$ 530). 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 27 October 2026.
Discover the top 6 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 27 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 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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