Cheapest return flights from Chicago to San Jose in July from $568

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 July 2025 (see full year).

Return flights

09 Jul - 30 Jul Southwest Airlines
07 Jul - 16 Jul Southwest Airlines
05 Jul - 13 Jul Southwest Airlines
10 Jul - 30 Jul Southwest Airlines
21 Jul - 01 Aug Southwest Airlines
08 Jul - 30 Jul Southwest Airlines
10 Jul - 18 Jul Southwest Airlines
03 Jul - 17 Jul Southwest Airlines
12 Jul - 20 Jul Southwest Airlines
11 Jul - 13 Jul Southwest Airlines
12 Jul - 15 Jul Southwest Airlines

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

Skyscanner

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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