Cheapest return flights from Chicago to San Jose in May from $361

AirHint found the following cheapest return flights from Chicago (ORD) to San Jose (SJO) in May 2026 (see full year).

Return flights

08 May - 28 May Viva
18 May - 03 Jun Spirit Airlines
02 May - 09 May Frontier Airlines
08 May - 10 May Viva
08 May - 14 May Viva
23 May - 29 May Frontier Airlines
03 May - 10 May Spirit Airlines
14 May - 18 May Spirit Airlines
16 May - 27 May Frontier Airlines
16 May - 28 May Spirit Airlines
03 May - 14 May Spirit Airlines
30 May - 06 Jun Copa
19 May - 02 Jun Copa
29 May - 01 Jun United
30 May - 20 Jun United
29 May - 05 Jun United
31 May - 20 Jun Copa
16 May - 01 Jun Spirit Airlines
31 May - 01 Jun Spirit Airlines
22 May - 01 Jun Viva

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

Powered by

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

Feel free to contact us with any feedback or request another flight research.