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 24/3. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
16 Feb — 23 Feb1
Round-trip
1 adult
Economy
The best prices from Calgary to Chicago are usually found in February or January, booked 66 days in advance, depart on a Thursday or Friday and return on a Monday
Cheap 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 11 February 2025.
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 11 February 2025.
Thu 20/211:30 a.m.YYC - ORD
Nonstop3h 26mWestJet
Thu 27/24:45 p.m.ORD - YYC
Nonstop3h 51mWestJet
Deal found 10/2C$ 186
Fri 2/51:30 p.m.YYC - ORD
1 stop9h 59mMultiple Airlines
Mon 5/55:30 p.m.ORD - YYC
Nonstop3h 49mMultiple Airlines
Deal found 11/2C$ 238
Mon 17/37:20 p.m.YYC - ORD
1 stop13h 13mUnited Airlines
Wed 26/32:35 p.m.ORD - YYC
1 stop8h 06mUnited Airlines
Deal found 11/2C$ 245
Thu 13/38:30 a.m.YYC - ORD
1 stop9h 11mAir Canada
Thu 20/312:58 p.m.ORD - YYC
1 stop11h 20mAir Canada
Deal found 11/2C$ 287
Tue 11/37:40 a.m.YYC - ORD
1 stop9h 06mDelta
Tue 18/312:15 p.m.ORD - YYC
2 stops12h 01mDelta
Deal found 11/2C$ 312
Fri 21/24:35 p.m.YYC - MDW
1 stop11h 46mMultiple Airlines
Sun 23/28:44 p.m.MDW - YYC
1 stop27h 11mMultiple Airlines
Deal found 10/2C$ 396
Fri 7/36:59 p.m.YYC - ORD
2 stops17h 05mAlaska Airlines
Tue 11/32:00 p.m.ORD - YYC
1 stop29h 09mAlaska Airlines
Deal found 10/2C$ 426
Thu 10/46:30 a.m.YYC - MDW
1 stop6h 47mDelta
Sun 13/410:25 a.m.MDW - YYC
2 stops13h 51mDelta
Deal found 11/2C$ 428
Fri 7/31:28 p.m.YYC - ORD
Nonstop3h 31mAmerican Airlines
Tue 11/35:00 a.m.ORD - YYC
1 stop7h 49mAmerican Airlines
Deal found 10/2C$ 460
Sat 12/44:20 p.m.YYC - MDW
1 stop17h 00mPorter Airlines
Mon 21/411:15 a.m.MDW - YYC
1 stop13h 15mPorter Airlines
Deal found 11/2C$ 712
Tue 8/46:30 a.m.YYC - MDW
1 stop10h 48mWestJet
Sat 12/47:13 p.m.MDW - YYC
1 stop26h 29mWestJet
Deal found 11/2C$ 737
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 11 February 2025.
Thu 20/311:30 a.m.YYC - ORD
Nonstop3h 26mWestJet
Mon 24/34:45 p.m.ORD - YYC
Nonstop3h 51mWestJet
Deal found 10/2C$ 186
Fri 2/51:30 p.m.YYC - ORD
1 stop9h 59mMultiple Airlines
Mon 5/55:30 p.m.ORD - YYC
Nonstop3h 49mMultiple Airlines
Deal found 11/2C$ 238
Mon 17/37:20 p.m.YYC - ORD
1 stop13h 13mUnited Airlines
Wed 26/32:35 p.m.ORD - YYC
1 stop8h 06mUnited Airlines
Deal found 11/2C$ 245
Thu 13/38:30 a.m.YYC - ORD
1 stop9h 11mAir Canada
Thu 20/312:58 p.m.ORD - YYC
1 stop11h 20mAir Canada
Deal found 11/2C$ 287
Tue 11/37:40 a.m.YYC - ORD
1 stop9h 06mDelta
Tue 18/31:45 p.m.ORD - YYC
1 stop10h 31mDelta
Deal found 11/2C$ 312
Fri 7/36:59 p.m.YYC - ORD
2 stops17h 05mAlaska Airlines
Tue 11/32:00 p.m.ORD - YYC
1 stop29h 09mAlaska Airlines
Deal found 10/2C$ 426
Fri 7/31:28 p.m.YYC - ORD
Nonstop3h 31mAmerican Airlines
Tue 11/35:00 a.m.ORD - YYC
1 stop7h 49mAmerican Airlines
Deal found 10/2C$ 460
Sat 12/44:20 p.m.YYC - MDW
1 stop17h 00mPorter Airlines
Mon 21/411:15 a.m.MDW - YYC
1 stop13h 15mPorter Airlines
Deal found 11/2C$ 712
Fri 21/24:35 p.m.YYC - MDW
1 stop11h 46mMultiple Airlines
Sun 23/28:44 p.m.MDW - YYC
1 stop27h 11mMultiple Airlines
Deal found 10/2C$ 396
Thu 10/46:30 a.m.YYC - MDW
1 stop6h 47mDelta
Sun 13/410:25 a.m.MDW - YYC
2 stops13h 51mDelta
Deal found 11/2C$ 428
Tue 8/46:30 a.m.YYC - MDW
1 stop10h 48mWestJet
Sat 12/47:13 p.m.MDW - YYC
1 stop26h 29mWestJet
Deal found 11/2C$ 737
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 11 February 2025.
Thu 20/311:30 a.m.YYC - ORD
Nonstop3h 26mWestJet
Mon 24/34:45 p.m.ORD - YYC
Nonstop3h 51mWestJet
Deal found 10/2C$ 186
Fri 2/512:15 p.m.YYC - ORD
Nonstop3h 29mDelta
Mon 5/55:30 p.m.ORD - YYC
Nonstop3h 49mDelta
Deal found 11/2C$ 308
Sun 13/41:17 p.m.YYC - ORD
Nonstop3h 32mAmerican Airlines
Tue 22/49:50 a.m.ORD - YYC
Nonstop3h 45mAmerican Airlines
Deal found 11/2C$ 490
Tue 11/312:41 p.m.YYC - ORD
Nonstop3h 29mUnited Airlines
Tue 18/38:47 a.m.ORD - YYC
Nonstop3h 52mUnited Airlines
Deal found 11/2C$ 494
Tue 11/312:41 p.m.YYC - ORD
Nonstop3h 29mAir Canada
Wed 12/38:47 a.m.ORD - YYC
Nonstop3h 52mAir Canada
Deal found 9/2C$ 629
Last-minute flights from Calgary to Chicago
Discover last-minute flight deals from Calgary to Chicago. Data last updated 11 February 2025 and is based on user searches.
Sun 16/26:35 a.m.YYC - ORD
1 stop9h 54mDelta
Wed 19/312:15 p.m.ORD - YYC
1 stop9h 27mDelta
Deal found 11/2C$ 430
Sun 16/26:35 a.m.YYC - MDW
1 stop10h 08mDelta
Wed 19/310:25 a.m.MDW - YYC
2 stops9h 40mDelta
Deal found 11/2C$ 453
Sun 16/212:41 p.m.YYC - ORD
Nonstop3h 27mAir Canada
Wed 19/312:58 p.m.ORD - YYC
1 stop11h 20mAir Canada
Deal found 11/2C$ 532
Thu 20/211:30 a.m.YYC - ORD
Nonstop3h 26mWestJet
Thu 27/24:45 p.m.ORD - YYC
Nonstop3h 51mWestJet
Deal found 10/2C$ 186
Thu 20/211:30 a.m.YYC - ORD
Nonstop3h 26mMultiple Airlines
Thu 27/210:45 p.m.ORD - YYC
1 stop25h 10mMultiple Airlines
Deal found 10/2C$ 265
Thu 20/26:35 a.m.YYC - MDW
1 stop5h 07mWestJet
Thu 27/210:19 a.m.MDW - YYC
2 stops9h 46mWestJet
Deal found 11/2C$ 876
Fri 21/24:35 p.m.YYC - MDW
1 stop11h 46mMultiple Airlines
Sun 23/28:44 p.m.MDW - YYC
1 stop27h 11mMultiple Airlines
Deal found 10/2C$ 396
Fri 21/26:59 p.m.YYC - ORD
2 stops17h 05mAlaska Airlines
Sun 23/24:05 p.m.ORD - YYC
2 stops27h 04mAlaska Airlines
Deal found 10/2C$ 767
Fri 21/21:32 p.m.YYC - ORD
Nonstop3h 31mAmerican Airlines
Sun 23/29:50 a.m.ORD - YYC
Nonstop4h 02mAmerican Airlines
Deal found 10/2C$ 943
Fri 21/27:40 a.m.YYC - MDW
2 stops27h 30mPorter Airlines
Sun 23/21:05 p.m.MDW - YYC
2 stops33h 00mPorter Airlines
Deal found 10/2C$ 2,168
Sun 2/311:30 a.m.YYC - ORD
Nonstop3h 26mMultiple Airlines
Thu 6/39:47 p.m.ORD - YYC
1 stop26h 08mMultiple Airlines
Deal found 10/2C$ 262
Fri 7/36:59 p.m.YYC - ORD
2 stops17h 05mAlaska Airlines
Tue 11/32:00 p.m.ORD - YYC
1 stop29h 09mAlaska Airlines
Deal found 10/2C$ 426
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 11 February 2025.
Mon 24/311:30 a.m.YYC - ORD
Nonstop3h 26mWestJet
Deal found 10/2C$ 125
Fri 11/48:30 a.m.YYC - ORD
1 stop9h 24mAir Canada
Deal found 11/2C$ 156
Fri 21/26:14 a.m.YYC - ORD
1 stop12h 41mUnited Airlines
Deal found 10/2C$ 159
Wed 9/76:35 a.m.YYC - MDW
1 stop5h 27mDelta
Deal found 10/2C$ 186
Tue 8/47:40 a.m.YYC - ORD
2 stops12h 05mDelta
Deal found 9/2C$ 193
Mon 24/39:45 p.m.YYC - MDW
2 stops17h 08mMultiple Airlines
Deal found 10/2C$ 202
Mon 10/39:45 p.m.YYC - ORD
2 stops17h 53mMultiple Airlines
Deal found 9/2C$ 204
Sun 2/36:59 p.m.YYC - ORD
1 stop9h 54mAlaska Airlines
Deal found 10/2C$ 219
Wed 19/21:32 p.m.YYC - ORD
Nonstop3h 31mAmerican Airlines
Deal found 11/2C$ 275
Sat 29/37:40 a.m.YYC - MDW
2 stops25h 40mPorter Airlines
Deal found 11/2C$ 317
Wed 2/710:30 a.m.YYC - MDW
1 stop6h 33mWestJet
Deal found 11/2C$ 416
Find flights from Calgary to Chicago within your budget
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 629,999 searches. Data last updated 11 February 2025.
Fly from
Any airport
Fly to
Any airport
Route
Depart
Return
Price
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Thu 20/3
11:30 a.m.-3:56 p.m.
Nonstop3h 26m
Chicago O'Hare Intl
Mon 24/3
4:45 p.m.-7:36 p.m.
Nonstop3h 51m
C$ 186
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Fri 2/5
1:30 p.m.-12:29 a.m.
1 stop9h 59m
Chicago O'Hare Intl
Mon 5/5
5:30 p.m.-8:19 p.m.
Nonstop3h 49m
C$ 238
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Mon 17/3
7:20 p.m.-9:33 a.m.
1 stop13h 13m
Chicago O'Hare Intl
Wed 26/3
2:35 p.m.-9:41 p.m.
1 stop8h 06m
C$ 245
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Thu 13/3
8:30 a.m.-6:41 p.m.
1 stop9h 11m
Chicago O'Hare Intl
Thu 20/3
12:58 p.m.-11:18 p.m.
1 stop11h 20m
C$ 287
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Tue 11/3
7:40 a.m.-5:46 p.m.
1 stop9h 06m
Chicago O'Hare Intl
Tue 18/3
1:45 p.m.-11:16 p.m.
1 stop10h 31m
C$ 312
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
Fri 21/2
4:35 p.m.-5:21 a.m.
1 stop11h 46m
Chicago Midway
Sun 23/2
8:44 p.m.-10:55 p.m.
1 stop27h 11m
C$ 396
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Fri 7/3
6:59 p.m.-1:04 p.m.
2 stops17h 05m
Chicago O'Hare Intl
Tue 11/3
2:00 p.m.-6:09 p.m.
1 stop29h 09m
C$ 426
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
Thu 10/4
6:30 a.m.-2:17 p.m.
1 stop6h 47m
Chicago Midway
Sun 13/4
10:25 a.m.-11:16 p.m.
2 stops13h 51m
C$ 428
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Fri 7/3
1:28 p.m.-5:59 p.m.
Nonstop3h 31m
Chicago O'Hare Intl
Tue 11/3
5:00 a.m.-11:49 a.m.
1 stop7h 49m
C$ 460
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
Sat 12/4
4:20 p.m.-10:20 a.m.
1 stop17h 00m
Chicago Midway
Mon 21/4
11:15 a.m.-11:30 p.m.
1 stop13h 15m
C$ 712
Flights are sorted by cheapest round-trip flights first.
Deals found on 10/2
Showing 1-10 of 22 results
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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.
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.
Travel insights for flights from Calgary to Chicago
Get recent, data-driven insights about flights from Calgary to Chicago including ideal travel times, pricing trends, and more.
How far ahead should I book a flight from Calgary to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Calgary to Chicago. Price data was last updated on 7 February 2025.
To ensure you get the cheapest price possible for a flight from Calgary to Chicago, you should look to book at least 66 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.
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$ 261). Flying from Calgary to Chicago in March is currently the most expensive (average of C$ 355). 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 11 February 2025.
One of the essential ways to save on airfare from Calgary to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 76% on airfare.
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).
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 11 February 2025.
See what other customers who have flown with Alaska Airlines, Delta and Porter Airlines from Calgary to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.