Chicago Loop Walking Tour

Art Institute of Chicago

Home to one of the world’s premier art collections, this museum combines timeless masterpieces like American Gothic with elegant Beaux-Arts architecture. Step inside to explore artworks spanning centuries, cultures, and styles.

Buckingham Fountain

Modeled after the fountains of Versailles, this Chicago icon is among the world’s largest and most spectacular. Its choreographed water shows reach heights of up to 150 feet, framed by the city’s dazzling skyline.

Chicago Board of Trade Building

This iconic Art Deco skyscraper once served as the centerpiece of Chicago’s financial district. Topped with a statue of Ceres, goddess of agriculture, it showcases the city’s trading heritage inside its grand lobby.

Chicago Cultural Center

Once the city’s main library, this architectural gem is now a vibrant public arts space. Inside, its intricate mosaics and breathtaking stained-glass domes make it a cultural treasure worth visiting.

DuSable Bridge

Spanning the Chicago River, this double-deck bascule bridge connects the city’s north and south sides. Its decorative towers pay tribute to Chicago’s founder, Jean Baptiste Point du Sable, and celebrate key moments in city history.

Cloud Gate (The Bean)

Chicago’s most recognizable sculpture reflects the skyline in its mirror-like surface. Walk beneath its arching curves to see the city—and yourself—from a whole new angle.

Crown Fountain

Two glass block towers face one another, displaying digital portraits that spout water during the summer months. This interactive installation delights visitors of all ages while blending art and play.

Jay Pritzker Pavilion

Designed by renowned architect Frank Gehry, this striking outdoor performance venue anchors Millennium Park. Its flowing steel ribbons and advanced acoustics create an unforgettable concert experience in the heart of the city.

Millennium Monument

A modern reimagining of a 1917 colonnade, this elegant semicircular structure honors Chicago’s founders. It offers a graceful reminder of the city’s classical roots amid the park’s contemporary design.

Flamingo in Federal Plaza

Alexander Calder’s vivid red Flamingo stands out boldly among the Loop’s modernist buildings. Its sweeping steel curves bring energy and contrast to the surrounding glass and concrete.

The Marquette Building

An 1895 gem of the Chicago School, this early skyscraper features detailed terra cotta and a radiant interior rotunda. Its intricate mosaics commemorate the journeys of the city’s first explorers.

The Picasso in Daley Plaza

Gifted to the city by Pablo Picasso, this monumental abstract sculpture has become a Chicago favorite. Its form defies explanation, sparking curiosity and conversation among all who see it.

The Rookery Building

One of Chicago’s oldest surviving high-rises, the Rookery features a luminous light court redesigned by Frank Lloyd Wright. Its mix of Romanesque Revival and early skyscraper style makes it a true architectural marvel.

Willis Tower and Skydeck Chicago

Once the tallest building on Earth, Willis Tower still defines the city’s skyline. From the 103rd-floor Skydeck, step onto The Ledge—a glass balcony suspended high above the streets—for breathtaking views.

McCormick Bridgehouse and Chicago River Museum

Step inside this functioning bridgehouse to witness the giant gears that raise the Michigan Avenue Bridge. Exhibits inside tell the story of how the river shaped Chicago’s development.

Vietnam Veterans Memorial Plaza

This serene riverside memorial honors those who served in Vietnam. Its reflective granite walls capture both the city’s motion and the quiet remembrance of its heroes.

The River Theater

A cascading set of steps linking street level to the riverfront, the River Theater is a scenic spot to pause and take in skyline views. It serves as both a public gathering space and a graceful urban connection.

The Chicago Theatre

With its famous lighted marquee and opulent French Baroque design, the Chicago Theatre has been dazzling audiences since 1921. It remains one of the city’s most beloved cultural landmarks.

Harold Washington Library—Winter Garden

Crowned with a soaring glass atrium, this library offers a bright, peaceful retreat in the middle of downtown. The rooftop Winter Garden provides a tranquil place to relax and reflect.

Miró’s Chicago

Joan Miró’s colorful, surrealist sculpture adds a touch of whimsy to the Loop. Its playful abstract form invites visitors to interpret and enjoy it in their own way.