Cheapest return flights from Chicago to San Jose in December from $588

Best time to book flights for Chicago (ORD) to San Jose (SJO) flights at AirHint

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

Return flights

26 Dec - 30 Dec Avianca
28 Dec - 02 Jan Avianca
25 Dec - 31 Dec Aeromexico
27 Dec - 01 Jan Volaris
27 Dec - 05 Jan Volaris
25 Dec - 01 Jan Aeromexico
28 Dec - 03 Jan Avianca
27 Dec - 03 Jan Volaris
19 Dec - 01 Jan Aeromexico
21 Dec - 03 Jan WestJet

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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