Chicago, USA → Calgary, Canada

Flight deals from Chicago to Calgary, Canada | Secret Flying

May 19, 2026

Non-stop from Chicago to Calgary, Canada for only $296 roundtrip

Non-stop flights from Chicago to Calgary, Canada for only $296 roundtrip with United Airlines.

Flight deals from US cities to Calgary, Canada | Secret Flying

February 25, 2026

SUMMER: US cities to Calgary, Canada from only $161 roundtrip

Summer flights from US cities to Calgary, Canada from only $161 roundtrip.

Flight deals from Chicago to Toronto or Calgary, Canada | Secret Flying

December 27, 2023

Non-stop from Chicago to Toronto or Calgary, Canada from only $258 roundtrip (Feb-Jun dates)

Non-stop flights from Chicago to Toronto or Calgary, Canada from only $258 roundtrip with Air Canada.

Flight deals from is a huge sale departing US cities to Canada with American Airlines and Delta, | Secret Flying

November 17, 2019

Huge sale from US cities to Canada (& vice versa) (e.g. Dallas, Texas to Toronto, Canada for only $160 USD roundtrip)

There is a huge sale departing US cities to Canada with American Airlines and Delta, for example Dallas, Texas to Toronto, Canada for only $160 USD roundtrip. The sale also works in reverse.