Cheapest return flights from Chicago to San Jose in June from $359

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

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

Return flights

09 Jun - 16 Jun Frontier Airlines
01 Jun - 04 Jun Frontier Airlines
20 Jun - 24 Jun Frontier Airlines
07 Jun - 14 Jun Frontier Airlines
21 Jun - 29 Jun Southwest Airlines
21 Jun - 05 Jul Southwest Airlines
20 Jun - 27 Jun Southwest Airlines
20 Jun - 04 Jul Southwest Airlines
18 Jun - 22 Jun Southwest Airlines
21 Jun - 28 Jun Frontier Airlines
20 Jun - 28 Jun Frontier 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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