Cheapest return flights from Chicago to San Jose in May from 311€

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

13 May - 20 May Spirit Airlines
10 May - 17 May Spirit Airlines
08 May - 11 May Spirit Airlines
15 May - 18 May Spirit Airlines
02 May - 10 May Frontier Airlines
19 May - 31 May Spirit Airlines
28 May - 28 Jun Spirit Airlines
03 May - 17 May Spirit Airlines
23 May - 28 May Volaris
28 May - 01 Jun Spirit Airlines
25 May - 01 Jun Avianca
20 May - 23 May Spirit Airlines
19 May - 24 May Copa

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

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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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