Cheapest return flights from Chicago to San Jose in August from 368€

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

Return flights

11 Aug - 26 Aug Southwest Airlines
28 Aug - 03 Sep Southwest Airlines
09 Aug - 15 Aug Frontier Airlines
28 Aug - 04 Sep Southwest Airlines
08 Aug - 10 Aug Frontier Airlines
22 Aug - 26 Aug Southwest Airlines
12 Aug - 02 Sep Southwest Airlines
02 Aug - 09 Aug Frontier Airlines
28 Aug - 31 Aug Southwest Airlines
03 Aug - 07 Aug Southwest Airlines
10 Aug - 16 Aug Southwest Airlines
01 Aug - 07 Aug Frontier Airlines
01 Aug - 04 Aug Southwest Airlines

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

Skyscanner

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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