Alkenes are valuable synthetic intermediates present in natural products, bioactive compounds, and materials. Palladium-catalyzed CH olefination reactions have become an attractive alternative to the commonly used Pd-catalyzed Mizoroki–Heck cross-coupling since no prefunctionalization of the starting materials is required. Major efforts have been devoted to developing selective, efficient, and general palladium-catalyzed CH olefination reactions employing directing groups and ligands. Nowadays, the toolbox of palladium-catalyzed CH olefination reactions is enormous, permitting the olefination of a wide range of substrates at different positions. In this article, we will offer an overview of the most important palladium-catalyzed CH olefination reactions of arenes and alkanes.