Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from Calgary to Chicago is Air Canada.
Cheapest Month
July
Travel Period: April 2025 - March 2026
The cheapest month(s) to fly from Calgary to Chicago is July.
Cheapest Day of the Week
Wednesday
The cheapest day(s) of the week to fly from Calgary to Chicago is Wednesday.
What’s the most popular airline flying from Calgary to Chicago?
The most popular airline flying from Calgary to Chicago is WestJet. Find the latest flight deals on Wego.
How far is Chicago from Calgary?
The flight distance between Calgary and Chicago is 2251km. Check all available flights on Wego.
Popular Airlines Flying From Calgary to Chicago
Popular Destinations From Chicago
Popular Destinations From Calgary
Popular Hotels in Chicago
- Clarion Inn Elmhurst - Oak Brook near I-88, I-290, I-294
- The Royal Sonesta Chicago Downtown
- Club Quarters Hotel Central Loop
- The Ritz-Carlton, Chicago
- Fairmont Chicago at Millennium Park Gold Experience
- Swissôtel Chicago
- Pendry Chicago
- Hotel Felix Chicago
- Hotel Saint Clair
- Best Western River North Hotel
