Cheap flights from Calgary to Chicago from C$ 139
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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
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 20 February 2025.
Round-trip from | C$ 226 |
---|---|
One-way from | C$ 139 |
Popular in | December |
Cheapest in | February |
Average price | C$ 284 |
Good round-trip deal | C$ 402 or less |
Good one-way deal | C$ 245 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 20 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 20 February 2025.
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 20 February 2025.
Fly from
Fly to
Route
Depart
Return
Price
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Mon 14/4
11:30 a.m.-3:56 p.m.
Nonstop3h 26m
Chicago O'Hare Intl
Sun 20/4
4:45 p.m.-7:36 p.m.
Nonstop3h 51m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Mon 7/4
8:30 a.m.-6:54 p.m.
1 stop9h 24m
Chicago O'Hare Intl
Thu 10/4
10:53 a.m.-8:23 p.m.
1 stop10h 30m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Thu 10/4
12:43 p.m.-5:10 p.m.
Nonstop3h 27m
Chicago O'Hare Intl
Sat 12/4
1:05 p.m.-9:48 p.m.
1 stop9h 43m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Sun 2/3
11:30 a.m.-3:56 p.m.
Nonstop3h 26m
Chicago O'Hare Intl
Sun 9/3
5:00 a.m.-2:21 p.m.
1 stop10h 21m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Fri 7/3
12:40 p.m.-9:27 p.m.
1 stop7h 47m
Chicago O'Hare Intl
Tue 11/3
1:26 p.m.-11:16 p.m.
2 stops10h 50m
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
Wed 12/3
6:30 a.m.-2:15 p.m.
1 stop6h 45m
Chicago Midway
Wed 10/9
10:10 a.m.-11:03 p.m.
2 stops13h 53m
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
Sat 15/3
3:45 p.m.-5:30 a.m.
1 stop12h 45m
Chicago Midway
Wed 19/3
9:25 a.m.-5:02 p.m.
1 stop8h 37m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
Thu 15/5
1:18 p.m.-5:48 p.m.
Nonstop3h 30m
Chicago O'Hare Intl
Sun 18/5
6:00 a.m.-9:50 p.m.
1 stop16h 50m
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
Tue 13/5
4:30 p.m.-4:24 p.m.
1 stop22h 54m
Chicago Midway
Thu 15/5
9:15 a.m.-10:30 p.m.
2 stops14h 15m
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
Wed 13/8
10:30 a.m.-6:03 p.m.
1 stop6h 33m
Chicago Midway
Mon 18/8
9:20 a.m.-4:48 p.m.
1 stop8h 28m
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.
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 14 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 20 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.
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 20 February 2025.
The most flights from YYC to CHI are scheduled on a Thursday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).
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 20 February 2025.
See what other customers who have flown with Delta, Porter Airlines and United 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.
Boarding
Entertainment
Crew
Overall
Food
Comfort
Reviews
Aaron,Oct 2024
TUS - LAX
Boarding
Entertainment
Crew
Overall
Food
Comfort
Reviews
Aaron,Oct 2024
TUS - LAX
Boarding
Entertainment
Crew
Overall
Food
Comfort
Reviews
Aaron,Oct 2024
TUS - LAX
Boarding
Entertainment
Crew
Overall
Food
Comfort
Reviews
Aaron,Oct 2024
TUS - LAX
Boarding
Entertainment
Crew
Overall
Food
Comfort
Reviews
Aaron,Oct 2024
TUS - LAX
Boarding
Entertainment
Crew
Overall
Food
Comfort
Reviews
Aaron,Oct 2024
TUS - LAX
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.
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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 20 February 2025.
Fly with Cheapflights
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How does Cheapflights help users find flights from Calgary to Chicago?
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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?
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