Cheapest return flights from Chicago to San Jose in August from $382

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

Return flights

13 Aug - 26 Aug Southwest Airlines
27 Aug - 03 Sep Southwest Airlines
13 Aug - 19 Aug Southwest Airlines
31 Aug - 06 Sep Southwest Airlines
12 Aug - 18 Aug Southwest Airlines
30 Aug - 06 Sep Southwest Airlines
03 Aug - 13 Aug Southwest Airlines
24 Aug - 30 Aug Southwest Airlines
14 Aug - 18 Aug Southwest Airlines
11 Aug - 15 Aug Southwest Airlines
02 Aug - 09 Aug Frontier Airlines
14 Aug - 17 Aug Southwest Airlines
10 Aug - 16 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.

Book a cheap hotel in San Jose

Cheap car rent in San Jose

Feel free to contact us with any feedback or request another flight research.