Cheapest return flights from Chicago to San Jose in September from $207

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

Return flights

11 Sep - 16 Sep Spirit Airlines
12 Sep - 16 Sep Spirit Airlines
12 Sep - 17 Sep Spirit Airlines
11 Sep - 17 Sep Spirit Airlines
13 Sep - 16 Sep Spirit Airlines
13 Sep - 17 Sep Spirit Airlines
16 Sep - 17 Sep Spirit Airlines
11 Sep - 30 Sep Spirit Airlines
12 Sep - 30 Sep Spirit Airlines
12 Sep - 29 Sep Spirit Airlines
11 Sep - 02 Oct Spirit Airlines
12 Sep - 02 Oct Spirit Airlines
13 Sep - 02 Oct Spirit Airlines
29 Sep - 11 Oct Spirit Airlines
28 Sep - 11 Oct Spirit Airlines
29 Sep - 15 Oct Spirit Airlines
28 Sep - 15 Oct Spirit Airlines
29 Sep - 09 Oct Spirit Airlines
28 Sep - 09 Oct Spirit Airlines
29 Sep - 02 Oct Spirit Airlines

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

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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