Cheapest one-way flights from Chicago to San Jose in December from 212€

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

One-Way flights

12 Dec Southwest Airlines
13 Dec Southwest Airlines
03 Dec Porter Airlines (Canada) Ltd
01 Dec Frontier Airlines
25 Dec Southwest Airlines
24 Dec Frontier Airlines
23 Dec Frontier Airlines
26 Dec Frontier Airlines

Also check the deals for return 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.

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.