A simple and beneficial strategy for the construction of 2,3‐dihydrofurans from α‐bromochalcones and α‐substituted cyanoketones via Michael addition‐alkylation reaction has been realized. This transformation was well compatible with various α‐bromochalcones and α‐substituted cyanoketones, and the corresponding multifunctionalized 2,3‐dihydrofurans were obtained in up to 98 % yield. A highly diastereoselective variant of the reaction was also developed. Moreover, the reaction could be performed on gram‐scale.