Cheapest return flights from Chicago to San Jose in April from $374

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
08 Apr - 15 Apr Southwest Airlines
18 Apr - 22 Apr Southwest Airlines
18 Apr - 28 Apr Southwest Airlines
18 Apr - 02 May Southwest Airlines
01 Apr - 08 Apr Southwest Airlines
25 Apr - 02 May Southwest Airlines
06 Apr - 10 Apr Frontier Airlines
02 Apr - 05 Apr Frontier Airlines
07 Apr - 14 Apr Southwest Airlines
18 Apr - 25 Apr Southwest Airlines
03 Apr - 06 Apr Frontier Airlines
11 Apr - 18 Apr Frontier Airlines

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

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