A favorite weekend escape for Chicagoans since the Gilded Age, when wealthy families built summer estates along the lakeshore and the town became the Newport of the Midwest. The drive from Chicago takes about 90 minutes. The lake itself — Geneva Lake — covers nearly 5,000 acres and stays remarkably clear, ringed by old-money cottages, working boathouses, and the kind of mature trees that take a century to grow.
The thing to do is the Geneva Lake Shore Path, a 21-mile trail that circumnavigates the entire lake on what was originally a Native American portage route. Parts of it pass through private lakeside estates by legal right-of-way, giving you an unusual close-up of the grand summer houses. You do not have to walk the full 21 miles — the ferry system that serves the lake allows you to cover sections and catch a boat back. In summer, canoes, kayaks, and paddleboards are available for rent, and the steamboat mailboat service from 1873 still runs daily, tossing mail from the boat to lakeside docks.
Winter brings a quieter, colder version of the same appeal. The area around town supports cross-country skiing and ice fishing on the lake, and the restaurants and shops of downtown Lake Geneva stay open year-round. If you are coming from Chicago in high summer, book ahead — this is one of those places where weekend accommodation fills up months out.