Cheapest one-way flights from Chicago to San Jose in January from $148

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

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

One-Way flights

09 Jan Frontier Airlines
10 Jan Frontier Airlines
13 Jan Frontier Airlines
25 Jan Frontier Airlines
26 Jan Delta
19 Jan Delta

Also check the deals for return 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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