Cheapest return flights from Chicago to San Jose in May from $259

Best time to book flights for Chicago (ORD) to San Jose (SJO) flights at AirHint

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

Return flights

27 May - 30 May Spirit Airlines
27 May - 03 Jun Spirit Airlines
25 May - 07 Jun Frontier Airlines
27 May - 04 Jun Spirit Airlines
31 May - 07 Jun Spirit Airlines
22 May - 31 May Spirit Airlines
31 May - 04 Jun Spirit Airlines
20 May - 29 May Spirit Airlines
23 May - 30 May Spirit Airlines
24 May - 01 Jun Spirit Airlines
16 May - 20 May Spirit Airlines
06 May - 14 May Spirit Airlines
16 May - 19 May Spirit Airlines
22 May - 27 May Frontier Airlines
23 May - 27 May Spirit Airlines
06 May - 10 May Spirit Airlines

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