Cheapest return flights from Chicago to San Jose in December from $365

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

Return flights

05 Dec - 08 Dec Frontier Airlines
08 Dec - 15 Dec Frontier Airlines
05 Dec - 10 Dec Frontier Airlines
04 Dec - 11 Dec Frontier Airlines
31 Dec - 10 Jan Frontier Airlines
26 Dec - 31 Dec Frontier Airlines
03 Dec - 07 Dec Delta
31 Dec - 08 Jan Frontier Airlines
11 Dec - 16 Dec Southwest Airlines
29 Dec - 06 Jan Frontier Airlines
13 Dec - 16 Dec Southwest Airlines
25 Dec - 04 Jan Frontier Airlines
28 Dec - 05 Jan Frontier Airlines
20 Dec - 25 Dec Frontier Airlines
23 Dec - 27 Dec Frontier Airlines
23 Dec - 01 Jan Frontier Airlines
24 Dec - 03 Jan Frontier Airlines
26 Dec - 02 Jan Frontier Airlines
19 Dec - 01 Jan Frontier Airlines
28 Dec - 02 Jan Frontier Airlines

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

Powered by

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.

Book a cheap hotel in San Jose

Cheap car rent in San Jose

Feel free to contact us with any feedback or request another flight research.