Cheapest return flights from Chicago to Calgary in May from $139

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 - 30 May WestJet direct
13 May - 27 May WestJet direct
16 May - 25 May WestJet direct
13 May - 28 May WestJet direct
13 May - 24 May WestJet direct
16 May - 24 May WestJet direct
13 May - 25 May WestJet direct
13 May - 01 Jun WestJet direct
16 May - 01 Jun WestJet direct
16 May - 20 May WestJet direct
16 May - 27 May WestJet direct
09 May - 13 May WestJet direct
29 May - 01 Jun WestJet direct
16 May - 04 Jun WestJet direct
27 May - 10 Jun WestJet direct
29 May - 02 Jun WestJet direct
28 May - 11 Jun WestJet direct
28 May - 02 Jun WestJet direct
27 May - 18 Jun WestJet direct
30 May - 02 Jun Frontier Airlines

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

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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.

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