An effective indium-catalyzed oxidative cross-dehydrogenative coupling of electronically varied chromenes with 1,3-dicarbonyl compounds and aryl rings has been established. Both the C–H alkylation and arylation proceed smoothly at room temperature to afford diverse α-substituted chromene compounds in up to 91% yields. Besides these two types of C–H components, simple ketones like cyclohexanones also prove to be well tolerated.