Cheapest return flights from Chicago to Calgary in May from $180

Best time to book flights for Chicago (ORD) to Calgary (YYC) flights at AirHint

AirHint found the following cheapest return flights from Chicago (ORD) to Calgary (YYC) in May 2025 (see full year).

Return flights

16 May - 20 May United direct
10 May - 17 May United direct
29 May - 03 Jun WestJet direct
29 May - 02 Jun WestJet direct
29 May - 01 Jun WestJet direct
17 May - 23 May United
14 May - 17 May United
29 May - 31 May WestJet direct
16 May - 18 May WestJet direct
16 May - 19 May WestJet direct
09 May - 15 May Air Canada direct
09 May - 16 May United
05 May - 09 May United
31 May - 04 Jun Frontier Airlines
28 May - 02 Jun Delta
01 May - 01 Jun WestJet direct
23 May - 02 Jun WestJet direct
28 May - 02 Jun WestJet direct

Also check the deals for one-way flights from Chicago to Calgary in May.

Skyscanner

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

Book a cheap hotel in Calgary

Cheap car rent in Calgary