On sunny days, the 606, as it’s more commonly known (the name is taken from the start of Chicago ZIP codes), is one of the liveliest places in town, full of cyclists, joggers, and dog walkers. It’s the largest greenway on a former rail line in the country. New York City’s High Line may be more glamorous, but it’s smaller and not as practical for getting from one place to another.
You haven’t seen the Northwest Side unless you’ve walked or biked the Bloomingdale Trail, a 2.7-mile elevated path running between Ashland and Ridgeway Avenues. Related: Three Notable Locals Pick Their Favorite Things to Do Chef Damarr Brown, singer Kelly Hogan, and White Sox legend Ozzie Guillén share their essential Chicago experiences.