The Chandra X-ray Observatory is providing remarkable new views of massive star-forming regions, revealing all stages in the life cycle of high-mass stars and their effects on their surroundings. We present a Chandra tour of several high-mass star-forming regions, highlighting physical processes that characterize the life of a cluster of high-mass stars, from deeply-embedded cores too young to have established an HII region to superbubbles so large that they shape our views of galaxies. Along the way we see that X-ray observations reveal hundreds of stellar sources powering great HII region complexes, suffused by both hard and soft diffuse X-ray structures caused by fast O-star winds thermalized in wind-wind collisions or by termination shocks against the surrounding media. Finally, we examine the effects of the deaths of high-mass stars that remained close to their birthplaces, exploding as supernovae within the superbubbles that these clusters created. We present new X-ray results on W51 IRS2E and 30 Doradus and we introduce new data on Trumpler 14 in Carina and the W3 HII region complexes W3 Main and W3(OH).