Walking Chicago: Self-Guided Tour of the Loop

This self-guided walking tour through downtown Chicago passes some of the city’s most famous sights. You’ll admire sculptures by Picasso and Calder, gaze at some of the city’s historic architecture, and finish with drinks and a view of the skyline. Start in the late afternoon and finish in time for happy hour at Cindy’s Rooftop Bar.

Total Distance: 2.5 miles
Total Walking Time: 1 hour

Start your exploration of Chicago’s Loop by taking the Brown/Pink/Orange L line to the LaSalle/Van Buren Station. Walk one block north on La Salle Street to the Chicago Board of Trade Building, a stunning art deco skyscraper. Power up with a power lunch at the Ceres Cafe in the building lobby.

highrise buildings in Chicago Loop
Walk to the Willis Tower to seek out the vies from the skydeck. Photo © Rebecca Holland.

Walk three blocks east on West Jackson Boulevard and enter the Willis Tower Skydeck. Take the high-speed elevator to the 103rd floor observation deck for views across Chicago into four neighboring states.

Exit the Willis Tower, walk one block north on South Franklin Street, then turn right onto North Adams Street. Walk three blocks east, then turn right on South LaSalle Street to step inside the Rookery Building. The stunning lobby was designed by Frank Lloyd Wright and includes a spiral staircase designed by architect John Root.

red metal art display in Chicago
The red Flamingo Sculpture in the Kluczynski Federal Building plaza. Photo © Alexandre Fagundes de Fagundes/Dreamstime.

Continue one block east on West Adams Street to Alexander Calder’s bright red, abstract Flamingo sculpture. The red color was designed to offset the black and steel dominating Federal Plaza.

Turn left onto North Dearborn Street and walk five blocks north toward The Picasso, located outside the Richard J. Daley Center. Unveiled in 1967, the 50-foot-tall sculpture was the first major piece of public art in Chicago.

Turn right on West Randolph Street and walk one block east, passing the 1926 Oriental Theatre. A peek inside the lobby reveals some of its elaborate interior. At North State Street, look left for a photo op of the Chicago Theatre’s flashing iconic marquee. Built in 1921, the theater still hosts plays and shows (tours are offered daily at noon).

red marquis sign over the Chicago Theater
Take a tour of the Chicago Theatre. Photo © Rebecca Holland.

Turn right on North State Street and walk one block south, then turn left onto East Washington Street. In two blocks you’ll reach the Chicago Cultural Center. Step inside to gaze upon one of the most beautiful interiors in the city.

Cross Michigan Avenue and enter Millennium Park. Snap your photo under Cloud Gate, admire the Crown Fountain, and wander through the Lurie Garden.

public art shaped like a bean in front of skyscrapers in Chicago's Loop
Snap a photo at the iconic Cloud Gate in Millennium Park. Photo © Rebecca Holland.

From Millennium Park, take the Nichols Bridgeway to cross south over East Monroe Street and enter The Art Institute of Chicago. Use the museum brochure to follow a self-guided tour through the impressive collection.

Exiting The Art Institute of Chicago, walk two blocks north up Michigan Avenue and stop in at the Chicago Athletic Association Hotel. Head up to Cindy’s Rooftop Bar for drinks with an amazing view over Millennium Park.

Rebecca Holland

About the Author

Rebecca Holland grew up in small town Wisconsin, visiting Chicago a few weekends a year to take in museum exhibits and see the sights. As she got older, Chicago became the place to go for parties, shopping, bachelorette parties, and special occasion dining.

Rebecca received her undergraduate degree in Journalism and Languages & Cultures of Asia from the University of Wisconsin, Madison, and moved to Washington, DC and then Rome, Italy. Her travels soon took her all over the globe, but Chicago was always in the back of her mind and remained her favorite city to visit. When it came time to move back to the US, there was no choice but Chicago, where she’s never felt more at home. She’s spent the last few years working as a full-time travel and food writer in the city, where she’s always looking for new local shops, exploring every inch of every neighborhood, taking day trips, and eating more food than is probably wise. She firmly believes that Chicago is the greatest food city in the country, and loves showing visitors around.

At the time of publication Rebecca was pursuing a Master’s degree in Journalism from the Medill School at Northwestern University. She is a contributor to New City, the Chicago Tribune, Roads & Kingdoms, and more.

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