Price observed over the last 3 months for a round trip.
Compare all flight tickets and find cheap flights from Calgary to Chicago
The cheapest flights right now
Calgary – Chicago
Outbound – Dec 3, 2026
direct
2h 33m Return – Dec 12, 2026
direct
4h 55m $339
3 days ago
Calgary – Chicago
Outbound – Dec 3, 2026
direct
2h 33m Return – Dec 12, 2026
1 stop
9h 18m DEN
$338
3 days ago
Calgary – Chicago
Outbound – Dec 3, 2026
direct
2h 33m Return – Dec 12, 2026
direct
4h 55m $402
3 days ago
* Prices are in USD per passenger, including taxes, for a round trip. Prices are based on searches carried out within the last 72 hours. Please note that availability and ticket prices are subject to change and should not be considered as the final price quoted.
Cheapest flight tickets
$208
Average price of a round trip
$298
Average flight ticket price recorded over the last 3 months for a round trip.
Flight duration
3h37
A flight from Calgary to Chicago takes on average 3h37.
Best time
July
According to user searches, the ideal month to go to Chicago is July.
Tips for finding a cheap flight from Calgary to Chicago
Check out our tips for booking your flight to Chicago (USA) from Calgary (Canada) at the cheapest possible price.
Usually, the cheapest month to pick up a ticket on this route is October, with an average flight ticket price of $280 (calculation over the last two years). The most touristic season corresponds to the months of October, November and January.
For the cheapest flights, it is advisable to buy your ticket at least 27 days before the departure date.
The airline offering the cheapest flight tickets is WestJet. A ticket from the airline WestJet to Chicago costs on average $308.
The airlines that offer the most flights are American Airlines, United Airlines and WestJet.
info departure city :
Calgary, Canada
airport :
Calgary International Airport (YYC)
local time :
Calgary is a city in the country Canada, the time zone is [[timezone]]. In Calgary, it is currently {fromLocalTime}, the temperature is on average 6°C, with a minimum of 2°C and a maximum of 12°C.
The city of Calgary has 1 airport(s): Calgary
destination info :
Chicago, USA
airports :
Chicago-Merrill C. Meigs Field Airport (CGX)
Chicago FSS (CHI)
Chicago-Midway International Airport (MDW)
Chicago-O'Hare International Airport (ORD)
local time :
Chicago is in the country USA, the time zone is [[timezone]]. In Chicago, it is currently {toLocalTime}, the temperature is on average 16°C, with a minimum of 15°C and a maximum of 18°C.
The city of Chicago (CHI) has 4 airport(s): Chicago-Merrill C. Meigs Field, Chicago FSS, Chicago-Midway and Chicago-O'Hare
Useful info about Chicago
What is the least touristic period to go to Chicago?
If you want to visit Chicago during the least touristic period, choose the month of July.
What is the most popular time to travel to Chicago?
In Chicago, the most popular month is October. It is during this period that the prices offered by airlines are also the highest.
When should I book my flight from Calgary to Chicago?
According to our data, it is recommended to book your flight 27 days before your departure. If you book your flight ticket 4 weeks before your departure, you may find a price below average. You can also choose morning flights that are 14% cheaper than afternoon and evening flights. The cheapest day to book a flight from Calgary to Chicago is Thursday.
What are the arrival and destination airports when traveling between Calgary and Chicago?
When you leave, you can leave from Calgary, and you will arrive at Chicago-O'Hare.
How to reach Calgary airport from the city centre?
This information is not available at this time.
Are there other means of transportation to go from Calgary to Chicago?
Airplane is the only means of transportation listed on Liligo for this journey.
Are there big differences in weather between Calgary and Chicago?
In summer, the average temperature is 22°C in Chicago and 16°C in Calgary. The average rainfall in summer is 145 mm in Chicago and 94 mm in Calgary. In summer, it is warmer in Chicago and it rains less in Calgary. In winter, it is colder in Chicago and it rains more in Chicago.
