Cheapest return flights from Chicago to San Jose in December from 292€

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
03 Dec - 07 Dec Delta
13 Dec - 20 Dec Southwest Airlines
18 Dec - 22 Dec Southwest Airlines
27 Dec - 02 Jan Frontier Airlines
19 Dec - 27 Dec Frontier Airlines
20 Dec - 03 Jan Frontier Airlines
19 Dec - 03 Jan Frontier Airlines
28 Dec - 02 Jan Frontier Airlines
22 Dec - 04 Jan Frontier Airlines

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

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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