Madison, WI
Get the best of both worlds in this urban nature haven just over two hours away from Chicago. Conveniently situated between two lakes, you’ll have readily accessible nature and great eateries at your fingertips. In this uber bike-friendly city, you can hop on a rental at any BCycle station and explore the sights—and restaurants—on two wheels. Art lovers will enjoy the 13-mile Lake Monona loop to spot outdoor sculptures, while nature lovers and beer enthusiasts will thrive along Lake Mendota’s Lakeshore Path, where you can pause at Memorial Union Terrace. During the summer months, the University of Wisconsin campus’ lakefront space features live music, brats and beer.