Cheapest one-way flights from Chicago to San Jose in April from $249

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 April 2025 (see full year).

One-Way flights

20 Apr Southwest Airlines

Also check the deals for return flights from Chicago to San Jose in April.

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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