Expansion of higher education and long-term economic growth have fostered high aspirations among adolescents. Recently, however, deteriorating labor force opportunities, particularly since the "Great Recession," and rising inequality have challenged the "American Dream." To assess how parental and adolescent outlooks have evolved over time, we examine shifts in future orientations across three generations of Midwest American families. Our unique data archive from the Youth Development Study includes 266 Generation 1 and Generation 2 parent-child dyads and 422 Generation 3 children. We assess change over two decades in parental expectations for their children's educational attainments (comparing G1 and G2) and in adolescents' socioeconomic aspirations, life course optimism, and anticipated work-family conflict (comparing G2 and G3). An initial between-families analysis examines aggregate change across generations; a second fixed-effects analysis assesses attitudinal differences between parents and children in the same families and the extent to which generational shifts in family circumstances and adolescents' educational performance account for change in adolescents' future orientations. We find that "millennial" adolescents had more positive outlooks than "Gen X" parents did at the same age. Generational increase in adolescent socioeconomic aspirations held even when socioeconomic origin, parent-child relationship quality, adolescent school performance, and other predictors were controlled. We find evidence that growing adolescent optimism across generations is attributable to rising parental educational expectations, increasing adolescent grades in school, and higher-quality parent-child relationships. We conclude that the "American Dream" is still alive for many contemporary parents and their adolescent children.