Cheapest return flights from Chicago to San Jose in October from 290€

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

Return flights

04 Oct - 07 Oct Southwest Airlines
07 Oct - 11 Oct Southwest Airlines
14 Oct - 17 Oct Southwest Airlines
12 Oct - 18 Oct Southwest Airlines
05 Oct - 11 Oct Southwest Airlines
23 Oct - 27 Oct Southwest Airlines
03 Oct - 10 Oct Southwest Airlines
08 Oct - 14 Oct Southwest Airlines
11 Oct - 15 Oct Southwest Airlines

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

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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