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

Return flights

08 Dec - 15 Dec	Delta
04 Dec - 11 Dec	Frontier Airlines
04 Dec - 10 Dec	Frontier Airlines
13 Dec - 19 Dec	Southwest Airlines
24 Dec - 31 Dec	Frontier Airlines
16 Dec - 22 Dec	Delta
03 Dec - 07 Dec	Delta
24 Dec - 03 Jan	Frontier Airlines
21 Dec - 02 Jan	Frontier Airlines
24 Dec - 04 Jan	Frontier Airlines
23 Dec - 01 Jan	Frontier Airlines
21 Dec - 01 Jan	Frontier Airlines
13 Dec - 16 Dec	Delta
28 Dec - 03 Jan	Frontier Airlines
28 Dec - 02 Jan	Frontier 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 263€

Return flights