Tagged Pages Archive | Flight Deals
2025
27
July
Calgary to Chicago, Illinois - $254 CAD roundtrip including taxes [Nonstop Flights]
27
July
United Airlines has dropped the price of their flights from Calgary to Chicago, Illinois down to $254 CAD roundtrip including taxes.
The flights are nonstop both ways.
Don't be fooled by the WestJet flights, which are a few dollars cheaper, but missing something rather important: the option to bring clothes with you.
UPDATE: Dates are available with American Airlines for $254 to $279 roundtrip, with carry-on included. Dates in September, October.
Availability for travel
December 2024
February, March, April, May, June, August, September, October, November 2025
How to find and book this deal
1. Start with the following Google Flights search:
Google Flights: Calgary to Chicago
- Click on the departure date box to open up the calendar view.
- Explore for the cheapest dates by adjusting the trip length at the bottom.
- Look for the dates that are $254 to $278 roundtrip
2. Go to Kayak or Skyscanner
3. Search for a flight from Calgary (YYC) to Chicago (ORD)
- Try the same dates you found on Google Flights.
Can't find this deal anymore? Prices change as deals sell out. The key is to be among the first to know when an amazing deal is posted.
Click here for tips on how to never miss a deal again.
screenshot from Kayak
Sign up for YYC Deals Alerts from Calgary
Go to the Alerts Page to sign up for flight deal alerts by e-mail, Facebook, or Twitter.
Travellers from Calgary also often sign up for alerts from Edmonton and Vancouver.
Join us in the YYC Deals Facebook Group
For live discussion of this deal, or to get some amazing travel advice (about anywhere) from your 50,000 fellow passengers in Calgary, join us in the:
YYC Deals Facebook Group.
^^^ click the 'Join Group' button when you arrive.
Hit Like if you like this deal! Click Share to show your friends on Facebook.
2025
26
July
Calgary to Penticton, BC - $56 (CB) to $194 CAD roundtrip including taxes [Nonstop Flights]
26
July
2025
26
July
Calgary to Anchorage, Alaska - $273 (CB) to $398 CAD roundtrip including taxes [Nonstop Flights]
26
July
2025
26
July
Calgary to Manila or Cebu, Philippines - $859 CAD roundtrip including taxes
26
July
2025
25
July
Calgary to Auckland or Christchurch, New Zealand - $912 CAD roundtrip including taxes
25
July
2025
20
July
Calgary to Singapore - $843 CAD roundtrip including taxes
20
July
2025
20
July
Calgary to London, and then Rome to Calgary - $485 to $536 CAD roundtrip including taxes [Nonstop Flights]
20
July
2025
18
July
Calgary to Bali, Thailand, Vietnam and other places in SE Asia - $853 to $953 roundtrip including taxes [Cathay Pacific]
18
July
2025
26
June
Calgary to Sydney, Australia - $863 CAD roundtrip including taxes
26
June
2025
14
June
Calgary to Boston - $276 CAD roundtrip including taxes [Nonstop Flights, CBO]
14
June
Sites