Cheap flights from Calgary to Chicago from C$ 132
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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
Cheapflights Tip: The best prices from Calgary to Chicago are usually found in February or May, booked 66 days in advance, depart on a Thursday or Friday and return on a Wednesday
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 25 March 2025.
Round-trip from | C$ 225 |
---|---|
One-way from | C$ 132 |
Popular in | December |
Cheapest in | February |
Average price | C$ 382 |
Good round-trip deal | C$ 452 or less |
Good one-way deal | C$ 272 or less |
Find flight deals from Calgary to Chicago
Cheapest flights from Calgary to ChicagoExplore 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 25 March 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 25 March 2025.
Cheapflights Fare Finder
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 25 March 2025.
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
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Sun 11/5
12:15 p.m.-4:44 p.m.
Nonstop3h 29m
Chicago O'Hare Intl
Tue 13/5
5:30 p.m.-8:19 p.m.
Nonstop3h 49m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Fri 23/5
12:38 p.m.-5:10 p.m.
Nonstop3h 32m
Chicago O'Hare Intl
Mon 26/5
5:02 a.m.-6:21 p.m.
1 stop14h 19m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Fri 2/5
12:25 a.m.-10:54 a.m.
1 stop9h 29m
Chicago O'Hare Intl
Fri 9/5
4:00 p.m.-11:43 p.m.
1 stop8h 43m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Tue 15/4
8:00 a.m.-9:31 p.m.
2 stops12h 31m
Chicago O'Hare Intl
Tue 22/4
12:15 p.m.-11:05 p.m.
2 stops11h 50m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Fri 6/6
6:29 a.m.-10:54 a.m.
Nonstop3h 25m
Chicago O'Hare Intl
Tue 10/6
8:25 p.m.-11:25 p.m.
Nonstop4h 00m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Fri 23/5
8:30 a.m.-1:03 p.m.
Nonstop3h 33m
Chicago O'Hare Intl
Mon 26/5
7:58 p.m.-7:25 a.m.
1 stop12h 27m
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
Tue 15/4
6:45 a.m.-5:19 p.m.
1 stop9h 34m
Chicago Midway
Tue 22/4
9:20 a.m.-8:47 p.m.
2 stops12h 27m
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
Fri 2/5
12:30 a.m.-9:33 a.m.
1 stop8h 03m
Chicago Midway
Fri 9/5
8:30 a.m.-7:40 p.m.
2 stops12h 10m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Thu 14/8
6:00 a.m.-11:39 p.m.
2 stops16h 39m
Chicago O'Hare Intl
Mon 18/8
8:42 p.m.-10:29 a.m.
1 stop14h 47m
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
Sun 11/5
7:00 a.m.-4:54 p.m.
2 stops32h 54m
Chicago Midway
Tue 13/5
9:40 a.m.-9:10 p.m.
2 stops12h 30m
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.
Cheapflights Insights
Everything you need to know about your flight from Calgary to Chicago
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 21 March 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 25 March 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 25 March 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.
Crew
Boarding
Comfort
Food
Entertainment
Overall
Reviews
Cheri,Jan 2025
FAT - SEA
Crew
Boarding
Comfort
Food
Entertainment
Overall
Reviews
Cheri,Jan 2025
FAT - SEA
Crew
Boarding
Comfort
Food
Entertainment
Overall
Reviews
Cheri,Jan 2025
FAT - SEA
Crew
Boarding
Comfort
Food
Entertainment
Overall
Reviews
Cheri,Jan 2025
FAT - SEA
Crew
Boarding
Comfort
Food
Entertainment
Overall
Reviews
Cheri,Jan 2025
FAT - SEA
Crew
Boarding
Comfort
Food
Entertainment
Overall
Reviews
Cheri,Jan 2025
FAT - SEA
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.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Calgary to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Calgary to Chicago
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 629,999 searches. Data last updated 25 March 2025.
Fly with Cheapflights
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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.