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

One-Way flights

19 Aug	Spirit Airlines
27 Aug	Spirit Airlines
26 Aug	Spirit Airlines
23 Aug	Spirit Airlines
22 Aug	Spirit Airlines
31 Aug	Spirit Airlines
07 Aug	Frontier Airlines
17 Aug	Spirit Airlines
28 Aug	Spirit Airlines
18 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 79€

One-Way flights