The distance is manageable, but the timeline is not casualA Chicago to Boston relocation is a genuine long-distance move, not a weekend errand. Learn the Boston moving permit rules earlyThis is the detail that surprises almost everyone coming from Chicago. The City of Boston requires a street occupancy permit to reserve curb space for a moving truck in most neighborhoods. The bottom lineA Chicago to Boston move is very doable, but the two cities reward different habits. Boston punishes one, because tight streets, older buildings, permit rules, and a crowded fall calendar all conspire against anyone who improvises.