Self-Guided Chicago Loop Tour Explore the City at Your Own Pace

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Self-Guided Chicago Loop Tour Explore the City at Your Own Pace

By Drives & Detours

Free cancellation available

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Features

Free cancellation available
2h 30m
Mobile voucher
Instant confirmation

Overview

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic city centre.

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 theatres, 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

Activity location

Buckingham Fountain
- Grant Park
- 60605, Chicago, Illinois, United States

Meeting/Redemption Point

DuSable Bridge
- 333 Michigan Avenue
- 60601, Chicago, Illinois, United States

Check availability

Self-Guided Chicago Loop Tour Explore the City at Your Own Pace in English

2h 30m
Opening hours: Wed 8:00-20:00
English

Travellers

Language options: English

Price details

S$12.93 x 1 AdultS$12.93

Total

What's included, what's not

Flexible Usage (unlimited access)
Audio Guide
App and Tour Download
Smartphone (bring your own)

Know before you book

Public transport options are available nearby
Suitable for all physical fitness levels
Works entirely offline once downloaded—no cell service required
GPS-triggered audio plays automatically based on your location
Flexible - Buy once, use any day/time—access never expires
Get the Drives & Detours app download the tour ahead of time

Activity itinerary

The Art Institute of Chicago (Pass by)

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.

Buckingham Fountain

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.

Chicago Board of Trade Building

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.

Chicago Cultural Center

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.

DuSable Bridge

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

Cloud Gate

Cloud Gate is better known as the Bean. The instantly recognisable 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.

Crown Fountain

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.

Jay Pritzker Pavilion (Pass by)

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.

Millennium Monument

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

Calder’s Flamingo

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

Marquette Building (Pass by)

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

Picasso Statue

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.

The Rookery Building

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.

Skydeck Chicago - Willis Tower (Pass by)

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.

The McCormick Bridgehouse & Chicago River Museum (Pass by)

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.

Vietnam Veterans Memorial

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

The Chicago Theatre (Pass by)

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

Harold Washington Library Center

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.

Miro's Chicago

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

Location

Activity location

Buckingham Fountain
- Grant Park
- 60605, Chicago, Illinois, United States

Meeting/Redemption Point

DuSable Bridge
- 333 Michigan Avenue
- 60601, Chicago, Illinois, United States

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