Cheapest return flights from Chicago to San Jose in January from $476

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

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

Return flights

19 Jan - 26 Jan Frontier Airlines
29 Jan - 02 Feb Southwest Airlines
14 Jan - 21 Jan Southwest Airlines
14 Jan - 20 Jan Southwest Airlines
05 Jan - 30 Jan Delta
12 Jan - 18 Jan Southwest Airlines
13 Jan - 19 Jan Southwest Airlines
08 Jan - 15 Jan Southwest Airlines
17 Jan - 20 Jan Southwest Airlines
21 Jan - 27 Jan Delta
16 Jan - 21 Jan Delta

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

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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