Cheapest return flights from Chicago to San Jose in May from $547

AirHint found the following cheapest return flights from Chicago (MDW) to San Jose (SJO) in May 2026 (see full year).

Return flights

16 May - 23 May Southwest Airlines
07 May - 22 May Southwest Airlines
14 May - 22 May Southwest Airlines
15 May - 22 May Southwest Airlines
22 May - 31 May Southwest Airlines
23 May - 30 May Porter Airlines (Canada) Ltd
23 May - 31 May Porter Airlines (Canada) Ltd

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

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