Cheapest return flights from Chicago to San Jose in October from $339

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

Return flights

21 Oct - 23 Oct Delta
23 Oct - 27 Oct Frontier Airlines
19 Oct - 22 Oct Southwest Airlines
18 Oct - 25 Oct Southwest Airlines
17 Oct - 20 Oct Southwest Airlines
24 Oct - 27 Oct Southwest Airlines
30 Oct - 02 Nov Southwest Airlines
24 Oct - 28 Oct Southwest Airlines
23 Oct - 28 Oct Southwest Airlines
03 Oct - 07 Oct Frontier Airlines
17 Oct - 19 Oct Southwest Airlines

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

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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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