Cheapest return flights from Chicago to San Jose in May from 406€

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

Return flights

07 May - 10 May Frontier Airlines
02 May - 09 May Frontier Airlines
04 May - 14 May Southwest Airlines
03 May - 08 May Southwest Airlines
10 May - 16 May Southwest Airlines
18 May - 03 Jun Southwest Airlines
07 May - 11 May Southwest Airlines
08 May - 24 Jun Southwest Airlines
14 May - 17 May Southwest Airlines
28 May - 01 Jun Southwest Airlines
26 May - 05 Jun Southwest Airlines
08 May - 26 Jun Southwest Airlines
15 May - 17 May Southwest Airlines
11 May - 17 May Southwest Airlines
21 May - 25 May Frontier Airlines

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

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