$96+ Cheap flights from Calgary (YYC) to Chicago (CHI)
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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Calgary to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.The best prices from Calgary to Chicago are usually found in January or February, booked 89 days in advance, depart on a Saturday or Tuesday and return on a Thursday
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 enero 17, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $158 (Jettzy) |
One-way from | $96 (Trip.com) |
Popular in | December |
Cheapest in | January |
Average price | $232 |
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 enero 17, 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 enero 17, 2025.
This Jettzy deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Air Canada deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Flightnetwork deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This United Airlines deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kissandfly.com deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Alaska Airlines deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Expedia deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 2,558,603 searches. Data last updated enero 17, 2025.
Fly from
Fly to
Route
Depart
Return
Price
CalgaryChicago
YYC - ORD
YYCORD
Calgary
dom. 3/2
11:30 am-3:56 pm
Nonstop3h 26m
Chicago O'Hare Intl
dom. 3/9
4:45 pm-7:36 pm
Nonstop3h 51m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
jue. 5/22
8:30 am-12:49 pm
Nonstop3h 19m
Chicago O'Hare Intl
mié. 5/28
2:40 pm-11:06 pm
1 stop9h 26m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
jue. 2/20
11:30 am-3:56 pm
Nonstop3h 26m
Chicago O'Hare Intl
jue. 2/27
4:00 pm-11:17 pm
1 stop8h 17m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
sáb. 2/8
6:35 am-3:30 pm
1 stop7h 55m
Chicago O'Hare Intl
mié. 2/19
1:45 pm-11:15 pm
1 stop10h 30m
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
lun. 2/10
7:00 am-5:43 pm
2 stops9h 43m
Chicago Midway
mié. 2/19
10:19 am-7:05 pm
2 stops9h 46m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
jue. 4/10
12:43 pm-5:10 pm
Nonstop3h 27m
Chicago O'Hare Intl
sáb. 4/12
5:00 am-1:53 pm
1 stop9h 53m
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
jue. 2/20
6:35 am-5:43 pm
1 stop10h 08m
Chicago Midway
jue. 2/27
5:10 am-9:52 pm
2 stops17h 42m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
mié. 4/23
1:17 pm-5:49 pm
Nonstop3h 32m
Chicago O'Hare Intl
dom. 4/27
9:50 am-12:32 pm
Nonstop3h 42m
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
jue. 4/10
7:44 am-6:18 pm
1 stop9h 34m
Chicago Midway
sáb. 4/12
11:22 am-7:40 pm
2 stops9h 18m
CalgaryChicago
YYC - MDW
YYCMDW
Calgary
jue. 2/13
7:10 am-12:10 pm
1 stop28h 00m
Chicago Midway
jue. 2/20
1:05 pm-11:40 am
1 stop23h 35m
Compare providers for flights from Calgary to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Calgary to Chicago in January.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Calgary-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Calgary-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Calgary-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Calgary-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Calgary-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
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 January 10, 2025.
To ensure you get the cheapest price possible for a flight from Calgary to Chicago, you should look to book at least 89 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, August is the cheapest month in which you can book a flight from Calgary to Chicago (average of $245). Flying from Calgary to Chicago in March is currently the most expensive (average of $320). 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 enero 17, 2025.
Unlike at noon, when flights are generally more expensive, you can save up to 49% on flights from Calgary to Chicago by exploring options for tickets in the afternoon.
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 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
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 enero 17, 2025.
Read reviews from past customers who have flown Air Canada, Delta and United Airlines from Calgary to Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
Entertainment
Overall
Food
Crew
Boarding
Reviews
Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Comfort