On the Beaten Path: Explore Chicago With a Walking Tour

These Chicago self-guided walking tours pack the best that the Windy City has to offer into a few short strolls. So leave your wheels behind and enjoy Chicago the way many locals do every day—by walking.

The Magnificent Mile

Cutting right through the heart of downtown Chicago, North Michigan Avenue—famously known as the Magnificent Mile—is home to some of the city's best shopping, dining and architecture. Start at the DuSable Bridge that spans the Chicago River. Walking north from the bridge, you'll quickly pass several iconic buildings, including the Gothic Tribune Tower, followed by a vibrant street lined with shops. This is a beautiful area to explore at night.

Stop for a bite at the Billy Goat Tavern, a low-key haunt that inspired SNL's famous "Cheezborger, Cheezborger" sketch. North of the shopping district, Michigan Avenue passes the Old Chicago Water Tower—one of the few structures to survive the Great Chicago Fire of 1871—and the beautiful Loyola University Museum of Art. As Michigan Avenue becomes Lake Shore Drive, this tour comes to an end at Oak Street Beach, a favorite local hangout in summer.

Navy Pier

This 2,000-foot pedestrian boardwalk is quite possibly the best place in Chicago to explore on foot. The longest pier in the world when it was first constructed in 1914, Navy Pier was re-imagined as a tourist attraction in the 1990s. Start your tour at Polk Bros Park at the entrance to the pier and pass through the historic facade of the Family Pavilion. Here you'll find shops, kiosks, the Chicago Children's Museum and the city's largest IMAX Theater.

Take the escalator up to Crystal Gardens, an indoor atrium spanning a full acre that harbors palm trees and other tropical plants. Exiting the atrium, you'll find yourself on the pier's upper level where you can ride the iconic Ferris wheel at Pier Park or play a round of miniature golf. Stroll along the promenade with its stunning views of the Chicago skyline and majestic ships that dock along the pier. Several restaurants along Navy Pier offer tasty bites—the Navy Pier Beer Garden is the perfect place to grab a beer, hear some live music and enjoy the cool breezes off the lake.

Millenium Park

Millennium Park packs a lot of things to see into a short distance. You can explore some of this 24.5-acre park's most famous landmarks in under half a mile, but you could also spend much more time on Millennium Park's meandering footpaths. Begin at Crown Fountain at the corner of Monroe Street and Michigan Avenue. It's a great place to people-watch or to cool your toes on a hot summer day.

Walk north through McCormick Tribune Plaza, then turn east up the stairs to view Cloud Gate up close. One of Chicago's most-photographed attractions, Cloud Gate is a massive, bean-shaped sculpture with a polished metal surface that offers a unique reflection of the downtown skyline. Continue east toward Jay Pritzker Pavilion and the Great Lawn, where outdoor concerts take place throughout summer, then walk to the lawn's south edge to visit the PB Bridge. Cross the bridge and head south and west to the lush wildflowers of Lurie Garden. For a bite to eat, stop at the nearby Park Grill or grab a drink at Tavern at the Park—and while you're there, head up to the roof to hang out in the tavern's Tree House.

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