Cheapest return flights from Chicago to San Jose in May from 335€

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

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

Return flights

10 May - 17 May Spirit Airlines
02 May - 05 May Spirit Airlines
10 May - 17 May United direct

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

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.

Book a cheap hotel in San Jose

Cheap car rent in San Jose