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

Return flights

27 Dec - 29 Dec	Copa
29 Dec - 13 Jan	Viva
19 Dec - 21 Dec	United	direct
23 Dec - 26 Dec	United
31 Dec - 08 Jan	Spirit Airlines
30 Dec - 13 Jan	Spirit Airlines
29 Dec - 16 Jan	Viva
29 Dec - 17 Jan	Viva
30 Dec - 16 Jan	Spirit Airlines
30 Dec - 17 Jan	Spirit Airlines
31 Dec - 08 Jan	American Airlines	direct
29 Dec - 07 Jan	Viva
29 Dec - 18 Jan	Viva
17 Dec - 23 Dec	United
17 Dec - 24 Dec	United
23 Dec - 25 Dec	United
19 Dec - 31 Dec	United
21 Dec - 25 Dec	United
18 Dec - 23 Dec	Spirit Airlines
20 Dec - 27 Dec	American Airlines

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

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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Cheapest return flights from Chicago to San Jose in December from $406

Return flights