Cheapest return flights from Chicago to San Jose in May from $469
AirHint found the following cheapest return flights from Chicago (MDW) to San Jose (SJO) in May 2025 (see full year).
Return flights
Also check the deals for one-way flights from Chicago to San Jose in May.
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.
