Cheapest return flights from Chicago to San Jose in April from 352€

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

Return flights

21 Apr - 05 May Southwest Airlines
18 Apr - 22 Apr Southwest Airlines
18 Apr - 02 May Delta
01 Apr - 08 Apr Southwest Airlines
25 Apr - 03 May Southwest Airlines
04 Apr - 11 Apr Frontier Airlines
05 Apr - 11 Apr Frontier Airlines
15 Apr - 20 Apr Southwest Airlines

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

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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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