Cheapest return flights from Chicago to San Jose in October from $225

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

Return flights

19 Oct - 08 Nov Spirit Airlines
21 Oct - 08 Nov Spirit Airlines
24 Oct - 08 Nov Spirit Airlines
29 Oct - 08 Nov Spirit Airlines
19 Oct - 02 Nov Spirit Airlines
19 Oct - 01 Nov Spirit Airlines
21 Oct - 02 Nov Spirit Airlines
19 Oct - 28 Oct Spirit Airlines
19 Oct - 25 Oct Spirit Airlines
19 Oct - 26 Oct Spirit Airlines
21 Oct - 01 Nov Spirit Airlines
18 Oct - 08 Nov Spirit Airlines
21 Oct - 28 Oct Spirit Airlines
21 Oct - 25 Oct Spirit Airlines
19 Oct - 27 Oct Spirit Airlines
19 Oct - 23 Oct Spirit Airlines
21 Oct - 26 Oct Spirit Airlines
24 Oct - 02 Nov Spirit Airlines
04 Oct - 11 Oct Spirit Airlines
21 Oct - 27 Oct Spirit 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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