AirHint found the following cheapest return flights from Chicago (ORD) to San Jose (SJO) in January 2026 (see full year).

Return flights

12 Jan - 31 Jan	Viva
24 Jan - 31 Jan	Spirit Airlines
24 Jan - 07 Feb	Spirit Airlines
12 Jan - 30 Jan	Viva
23 Jan - 30 Jan	Spirit Airlines
24 Jan - 09 Feb	Spirit Airlines
03 Jan - 10 Jan	Avianca
12 Jan - 25 Jan	Viva
18 Jan - 25 Jan	Avelo Airlines
12 Jan - 18 Jan	Viva
23 Jan - 31 Jan	Spirit Airlines
23 Jan - 07 Feb	Spirit Airlines
24 Jan - 25 Jan	Spirit Airlines
24 Jan - 12 Feb	Spirit Airlines
18 Jan - 07 Feb	Spirit Airlines
23 Jan - 09 Feb	Spirit Airlines
23 Jan - 12 Feb	Spirit Airlines

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

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 January from $289

Return flights