Chicago Walking Tour: The Best Outdoor Walks in Chicago

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Chicago is a very walkable city, and the best way to get a glimpse of local life is to go on a Chicago walking tour. Despite the urban setting, there are more than a few great strolls that can occupy an entire afternoon on a sunny day. Whether you’re looking for interesting people-watching, a peaceful nature stroll, or a peek into some gorgeous city homes, there’s a walk just waiting for you.

Lake Front Trail

On a warm, summer day, Chicago’s Lake Front Trail is more than bustling. Join a parade of bikers, rollerbladers, runners, and walkers on the narrow two-lane path and enjoy the refreshingly brisk lake breeze—just watch where you’re walking. The busy trail stretches 18 miles along the lakefront and connects the south side of Chicago to the north side. Hop on the trail at Navy Pier and head north toward North Avenue Beach for a leisurely two-mile stroll. One glimpse of the sand, volleyball nets, and beach bars, and you just might forget that you’re on a Chicago walking tour and not on the West Coast. Just before you reach North Avenue Beach, be sure to turn around—the views of the skyline from here are outstanding. The locals are friendly and likely more than willing to snap a photo of you with the postcard-perfect backdrop if you ask.

Lincoln Park

This 1,200-acre park is bigger than Central Park in New York and just as charming. Begin your one-mile walk of Lincoln Park at North Avenue and North Clark Street near the Chicago History Museum. From here, wind your way north up the shaded, tree-lined paths toward South Pond. Here, you find a surprisingly serene waterfront boardwalk basking under the sun. You’ve just stumbled upon a true urban oasis, so be sure to revel in the peacefulness. Make a stop at the bridge for some more postcard-worthy skyline views. There’s a reason wedding parties often stop here to pose—you might even see a photo session in progress. At the north end of the pond, you pass a charming café before entering the very well manicured Lincoln Park Zoo. Spend as long or as short as you’d like at this family-filled zoo (it’s free!) before continuing north to your final stop. The entrance to the always tranquil Alfred Caldwell Lily Pool is located near Fullerton Avenue and North Cannon Drive. This National Historic Landmark exudes romance, and you’re bound to see couples strolling hand-in-hand within the confines of this Impressionist painting of a gated garden.

The 606

Get a glimpse of urban living with a residential walk on the 606. The new path takes you through Chicago’s hottest northwest neighborhoods—including Wicker Park, Bucktown, and Logan Square—with art installations and green spaces along the way. This unused elevated train track was given a new life in June of 2015 as a 2.7 mile path. Start at Walsh Playground Park in Bucktown, then ascend the curved walkway onto the Bloomingdale Trail. Within minutes, you find yourself ogling the private gardens and roof decks of the mansions that line this manicured path. You feel like a local as you pass homes, churches, schools, and parks and get to see what it’s really like to live in Chicago.

Lake Front Trail

Lakefront Trail Chicago IL 60601

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