Chicago Winter Loop Historical Walking Tour

Join us for an unforgettable 2-hour walking tour through the downtown Loop area and the iconic Millennium Park. This guided experience is perfect for visitors who want to uncover the vibrant history, breathtaking architecture, and artistic gems of Chicago.
See the Chicago Theatre, where you'll marvel at its classic marquee and learn about its fascinating past as the "Wonder Theatre of the World." Stroll through the bustling streets of the Loop, exploring its architectural marvels and engaging in stories about the city’s dynamic history.

We'll visit Millennium Park, a cultural and artistic centerpiece of Chicago. You'll have the chance to admire Cloud Gate—affectionately called "The Bean"—and take in its stunning reflection of the city skyline.

Throughout the tour, your knowledgeable guide will provide engaging commentary, insider tips, and photo opportunities to ensure this is a Chicago experience you’ll never forget.

Meeting Point

The Chicago Theatre

175 N State St, Chicago, IL 60601, USA

Meet your guide in front of the Chicago Theatre at 175 N. State St. It is at the corner of State and Lake.

What's included:

• 2 Hour Walking Tour Suited for the Chicago Winter (indoor stops when its cold and rainy!)
• Professional Tour Guide

What to expect:

Duration: 2 hours

The Chicago Theatre

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

Chicago Theatre, often referred to as the "Wonder Theatre of the World," is a historic landmark known for its grand architecture and vibrant marquee. Located in downtown Chicago, it hosts a variety of performances, from concerts to comedy shows, attracting audiences from around the globe.

10 minutes

Marshall Field And Company Building

111 N State St, Chicago, 60602-1659, Illinois

Discover the history behind Chicago’s legendary department store.

10 minutes • Admission Ticket Included

Daley Bicentennial Plaza

337 E Randolph Dr, , Chicago, 60602-1305, Illinois

Admire the iconic Picasso sculpture that has become a city symbol

10 minutes

Chicago Loop

Chicago Loop, Chicago, IL, USA

The Loop, defined by its iconic elevated train tracks, is not only the city’s bustling commercial hub but also a symbol of resilience and rebirth. Learn about the devastating Great Chicago Fire of 1871 and marvel at the incredible modern metropolis that emerged from its ashes. Don’t forget to bundle up for this captivating tour!

30 minutes

Millennium Station

151 Michigan Ave, Chicago, IL 60602, USA

Learn about the elevated train system that gives the Loop its name.

10 minutes

Chicago Cultural Center

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

Gaze at stunning works of art made from delicate, colorful glass at the Tiffany Windows.

10 minutes

Cloud Gate

201 E Randolph St, Chicago, IL 60602, USA

Cloud Gate, commonly known as "The Bean," is a striking public sculpture located in Millennium Park, Chicago. Designed by artist Anish Kapoor, its reflective surface captures the city's skyline and invites visitors to interact with its unique shape and mirrored images.

5 minutes

Millennium Park

Chicago, 60602, Illinois

Millennium Park is a renowned urban space in the heart of Chicago, offering a mix of art, architecture, and lush greenery. It features iconic attractions like the Jay Pritzker Pavilion and Lurie Garden, making it a favorite destination for locals and tourists alike.

10 minutes