Cheapest return MDW–SJO flights, May

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

Return flights

20 May - 28 May Frontier Airlines
20 May - 27 May Frontier Airlines
20 May - 24 May Frontier Airlines
18 May - 03 Jun Frontier Airlines
10 May - 20 May Southwest Airlines
22 May - 30 May Allegiant Air
20 May - 30 May Frontier Airlines
20 May - 25 May Frontier Airlines
15 May - 21 May Southwest Airlines
23 May - 28 May Southwest Airlines
20 May - 26 May Frontier Airlines

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

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