Cheapest one-way flights from Chicago to San Jose in May from $132

AirHint found the following cheapest one-way flights from Chicago (ORD) to San Jose (SJO) in May 2026 (see full year).

One-Way flights

30 May Frontier Airlines
08 May Viva
06 May Frontier Airlines
03 May Frontier Airlines
29 May Viva
07 May Frontier Airlines
04 May Southwest Airlines
10 May Spirit Airlines
22 May Viva
21 May Spirit Airlines

Also check the deals for return 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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