Cheap flights from Calgary to Chicago
Cheapest current fares: $153 in September 2026, 2,224 km direct flight in ~2h 37m.
Cheapest month-by-month fares
Lowest available fare per calendar month from Calgary (YYC) to Chicago (ORD). Refreshed daily.
Calgary (YYC) → Chicago (ORD)
- September 2026 $153
- August 2026 $159
Frequently asked questions
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What is the cheapest month to fly from Calgary to Chicago?
Based on current 6-month forward fare data, September 2026 is the cheapest month to fly from Calgary (YYC) to Chicago (ORD), with fares starting from $153.
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What is the lowest current fare from YYC to ORD?
The lowest currently-listed fare from Calgary (YYC) to Chicago (ORD) is $153 on 2026-09-24.
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How long is the flight from Calgary to Chicago?
Direct flights from YYC to ORD cover approximately 2,224 km (1,382 miles), with an estimated flight time of 2h 37m. Operating airlines: AA, UA, WS.
Related guides for this route
Sibling pages — full route detail, airport overviews, visa context, per-airline routes.