Chicago Self-Guided Loop Architectural Tour

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown.
This journey unveils a blend of striking skyscrapers and hidden architectural gems, allowing you to explore at your own pace. Uncover the rich history from the Great Fire of 1871 to the architectural masterpieces that define the skyline.

Stroll past renowned theaters, museums, and captivating public art pieces that contribute to the city’s creative spirit.

The Loop offers a unique perspective on Chicago's past and present, whether it's your first visit or a familiar stroll.

— Self-guided exploration of Chicago’s historic Loop area
— Learn about the city’s architectural innovations and history
— Visit iconic landmarks like the Art Institute and Millennium Park
— Perfect for first-time visitors or seasoned Chicagoans alike

Meeting Point

DuSable Bridge

333 Michigan Ave, Chicago, IL 60601, USA

DuSable Bridge crosses the Chicago River on Michigan Avenue between East Wacker Drive and Illinois Street. Nearby landmarks include the Wrigley Building, Chicago Architecture Center, and Tribune Tower.

What's included:

• Flexible Usage (unlimited access)
• Audio Guide
• App and Tour Download

Not included:

• Smartphone (bring your own)

What to expect:

Duration: between 2 hours and 2 hours, 30 minutes

The Art Institute of Chicago

111 S Michigan Ave, Chicago, 60603-6110, Illinois

This museum is home to one of the world’s finest art collections and blends iconic works such as American Gothic with a striking Beaux-Arts building. Step inside for masterpieces spanning centuries and continents.

Pass by without stopping

Clarence F. Buckingham Fountain

301 S. Columbus Dr, Grant Park, Chicago, 60605, Illinois

Inspired by Versailles and one of the largest fountains in the world, this Chicago landmark dazzles with choreographed water displays. Its central jet shoots 150 feet into the air against a skyline backdrop.

5 minutes

Chicago Board Of Trade Building

141 W Jackson Blvd, La Salle Street, Chicago, 60604-2992, Illinois

A soaring Art Deco tower that once defined the city’s financial district, crowned by a statue of Ceres, goddess of agriculture. Its lobby offers a glimpse into Chicago’s trading legacy.

5 minutes

Chicago Cultural Center

78 E Washington St, , Chicago, 60602-4801, Illinois

This former library is now a free cultural hub known for its stunning stained-glass domes. Step inside to discover art exhibits, performances, and breathtaking architectural details.

5 minutes

DuSable Bridge

333 Michigan Ave, Chicago, IL 60601, USA

The double-deck, double-leaf bascule DuSable Bridge links Chicago’s north and south sides over the river. Its ornate towers honor the city’s founder and showcase moments from Chicago history.

5 minutes

Cloud Gate

201 E. Randolph St., Millenium Park, Chicago, 60602, Illinois

Cloud Gate is better known as the Bean. The instantly recognizable icon is a reflective sculpture that turns the skyline—and you—into part of the art. Walk beneath its gleaming surface for a unique visual experience.

5 minutes

Crown Fountain

201 E Randolph St, Millennium Park, Chicago, 60602, Illinois

Two glass block towers face each other, projecting video portraits that spray water in summer. This playful, interactive artwork invites visitors to cool off and connect with the city.

5 minutes

Jay Pritzker Pavilion

Millennium Park, Chicago, Illinois

Designed by Frank Gehry, the Jay Pritzker Pavilion is a sweeping outdoor concert venue that anchors Millennium Park. Its dramatic steel ribbons and state-of-the-art sound system create a one-of-a-kind urban stage.

Pass by without stopping

Millennium Monument

201 E Randolph St, Millennium Park, Wrigley Square, Chicago, 60601-6530, Illinois

A modern recreation of a 1917 colonnade, this semicircular landmark honors the city’s founders. It’s a graceful nod to Chicago’s classical past in a thoroughly modern park.

5 minutes

Calder’s Flamingo

50 W Adams St, Federal Plaza, Chicago, 60603-5107, Illinois

Alexander Calder’s massive red sculpture brings a bold splash of color to the heart of the Loop. Its sweeping curves contrast beautifully with the surrounding steel and glass.

5 minutes

Marquette Building

140 S Dearborn St, , Chicago, 60603-5202, Illinois

A masterpiece of the Chicago School, this 1895 high-rise boasts ornate terra cotta and a luminous interior rotunda. Its mosaics tell the story of the city’s early explorers.

Pass by without stopping

The Picasso

50 W Washington St, Richard J. Daley Plaza Civic Center, Chicago, 60602-1305, Illinois

A gift from Pablo Picasso, this abstract steel sculpture has become a beloved city icon. Its meaning is left to the imagination, sparking curiosity in all who pass by.

5 minutes

The Rookery Building

209 S La Salle St, , Chicago, 60604-1219, Illinois

The Rookery Building is one of Chicago’s oldest standing high-rises, featuring a stunning light court redesigned by Frank Lloyd Wright. Its blend of Romanesque and early skyscraper design is unforgettable.

5 minutes

Skydeck Chicago - Willis Tower

233 S Wacker Drive, Chicago, 60606-7147, Illinois

Once the tallest building in the world, this skyscraper offers panoramic city views from its 103rd-floor Skydeck. Step onto The Ledge for a glass-floor thrill.

Pass by without stopping

The McCormick Bridgehouse & Chicago River Museum

376 N Michigan Ave, Enter at Riverwalk Level, Chicago, 60601-3807, Illinois

Climb inside a working bridgehouse to see the gears that lift the Michigan Avenue Bridge. Exhibits explore the river’s role in Chicago’s growth.

Pass by without stopping

Vietnam Veterans Memorial

24 E Wacker Dr, Chicago, IL 60601, USA

The Vietnam Veterans Memorial Plaza is a peaceful riverside space that honors those who served, with polished granite walls reflecting names and memories. It’s a place for reflection amid the bustle of downtown.

5 minutes

The Chicago Theatre

175 N State St, , Chicago, 60601-3623, Illinois

With its iconic marquee and lavish French Baroque interior, this 1921 venue is a showstopper inside and out. The Chicago Theatre remains a centerpiece of Chicago’s entertainment scene.

Pass by without stopping

Harold Washington Library Center

400 S State St, , Chicago, 60605-1216, Illinois

Topped with a sunlit glass atrium, this public library offers a serene escape from the busy streets. Its Winter Garden feels like a hidden oasis.

5 minutes

Miro's Chicago

69 W Washington St, Chicago, 60602-3134, Illinois

This whimsical, colorful sculpture by Joan Miró brings a playful burst of surrealism to the Loop. Its abstract form invites endless interpretations.

5 minutes