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

Return flights

13 Jun - 22 Jun	Spirit Airlines
21 Jun - 28 Jun	Spirit Airlines
21 Jun - 26 Jun	Spirit Airlines
13 Jun - 20 Jun	Spirit Airlines
26 Jun - 14 Jul	Viva
26 Jun - 15 Jul	Viva
21 Jun - 27 Jun	Spirit Airlines
25 Jun - 29 Jun	Avianca
07 Jun - 14 Jun	Spirit Airlines
26 Jun - 29 Jun	Volaris
27 Jun - 14 Jul	Spirit Airlines
27 Jun - 15 Jul	Spirit Airlines
20 Jun - 27 Jun	United
06 Jun - 14 Jun	American Airlines
26 Jun - 04 Jul	Viva
21 Jun - 04 Jul	Spirit Airlines
26 Jun - 01 Jul	Viva
27 Jun - 01 Jul	Spirit Airlines
25 Jun - 14 Jul	Spirit Airlines
25 Jun - 15 Jul	Spirit Airlines

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

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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Cheapest return flights from Chicago to San Jose in June from $369

Return flights