AirHint found the following cheapest one-way flights from Chicago (ORD) to San Jose (SJO) in August 2025 (see full year).

One-Way flights

27 Aug	Southwest Airlines
21 Aug	Spirit Airlines
18 Aug	Spirit Airlines
06 Aug	Spirit Airlines
13 Aug	Spirit Airlines
09 Aug	Frontier Airlines
02 Aug	Frontier Airlines
04 Aug	Spirit Airlines
11 Aug	Spirit Airlines
07 Aug	Spirit Airlines

Also check the deals for return flights from Chicago to San Jose in August.

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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Cheapest one-way flights from Chicago to San Jose in August from 123€

One-Way flights