1. Empire Builder | Chicago, IL
Trip length: Up to 46 hours
The most epic winter adventure awaits on the Empire Builder, Amtrak’s 46-hour blissful trek from Chicago to Seattle and Portland. The train winds through Minneapolis and St. Paul and through Montana’s Glacier National Park, chugging away through America’s West. Private bedroom cars provide solace for a long-procrastinated crochet project or binging a book series, while communal dining offers the opportunity to meet new people. At night, let the sway of the speedy train lull you to sleep.