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

Return flights

27 Jan - 30 Jan	Frontier Airlines
22 Jan - 28 Jan	Southwest Airlines
20 Jan - 25 Jan	Delta
21 Jan - 25 Jan	Delta
30 Jan - 09 Feb	Southwest Airlines
18 Jan - 21 Jan	Southwest Airlines
22 Jan - 26 Jan	Southwest Airlines
19 Jan - 26 Jan	Southwest Airlines
30 Jan - 02 Feb	Southwest Airlines
31 Jan - 01 Feb	Southwest Airlines
28 Jan - 31 Jan	Delta
15 Jan - 21 Jan	Delta
16 Jan - 19 Jan	Southwest 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 375€

Return flights