Chicago sits at the southern tip of Lake Michigan with Wisconsin, Indiana, and Michigan all within easy reach. Naperville, only 30 miles west and a quick Metra ride away, offers a riverfront Riverwalk and the Naper Settlement living history museum — an easy half-day without a car. A ninety-minute drive north puts you in Lake Geneva, the Gilded Age resort town on the Wisconsin lake shore, where the 21-mile Geneva Lake Shore Path passes grand old estates and you can return by ferry.