Cheapest return flights from Chicago to San Jose in June from $495

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

Return flights

15 Jun - 20 Jun Southwest Airlines
14 Jun - 18 Jun Southwest Airlines
29 Jun - 06 Jul Southwest Airlines
26 Jun - 02 Jul Southwest Airlines
22 Jun - 28 Jun Frontier Airlines
19 Jun - 22 Jun Frontier Airlines
23 Jun - 29 Jun Frontier Airlines
30 Jun - 05 Jul Frontier Airlines
23 Jun - 26 Jun Frontier Airlines
14 Jun - 21 Jun Southwest Airlines
21 Jun - 27 Jun Southwest Airlines
21 Jun - 28 Jun Frontier Airlines
18 Jun - 22 Jun Southwest Airlines

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

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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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