Cheapest return flights from Chicago to San Jose in May from 405€

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 May 2025 (see full year).

Return flights

05 May - 12 May Frontier Airlines
06 May - 13 May Southwest Airlines
02 May - 10 May Southwest Airlines
10 May - 17 May Southwest Airlines
10 May - 22 May Southwest Airlines
03 May - 10 May Southwest Airlines
17 May - 24 May Southwest Airlines
17 May - 18 May Southwest Airlines
20 May - 27 May Southwest Airlines
24 May - 25 May Southwest Airlines

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

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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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