Chicago Iconic Landmarks Private Walking Tour

Uncover Chicago’s bold spirit through its iconic landmarks, from the Gothic Holy Name Cathedral to the gleaming Cloud Gate. Hear untold stories of resilience, art, and innovation. Optional: see the Chicago Theatre, Cultural Center, and Tiffany glass dome.
Explore Chicago’s vibrant downtown with a 5-Star Private Guide by your side
Discover iconic landmarks and skip the tourist traps with insider guidance
Walk deeper and see Cloud Gate, the Theatre, and more
Learn rich stories of Chicago’s architecture, history, and local legends
Get local tips on the best hidden gems and cultural spots to explore later

Meeting Point

The Peninsula Chicago

108 E Superior St, Chicago, IL 60611, USA

Meet your guide In front of The Peninsula Chicago, 108 E Superior St, Chicago, IL 60611, United States. Please do not enter the hotel, it is only a meeting point and the staff is not informed about the tour.

What's included:

• Private Walking Tour of Downtown Chicago’s Iconic Landmarks and Hidden Gems
• 5-Star Licensed Guide fluent in your chosen language
• Fascinating insights into Chicago’s architecture, history, and culture
• Insider tips on the best local attractions and hidden gems
• Extended walking route to the Chicago Theatre, Cultural Center, and Cloud Gate

Not included:

• Service tips

What to expect:

Duration: 3 hours

The Peninsula Chicago

108 E Superior St, Chicago, IL 60611, USA

Meet your guide In front of The Peninsula Chicago, 108 E Superior St, Chicago, IL 60611, United States. Please do not enter the hotel, it is only a meeting point and the staff is not informed about the tour.

10 minutes

Holy Name Cathedral

735 North State Street, , Chicago, 60654-3835, Illinois

Begin at the magnificent Holy Name Cathedral, a Gothic Revival masterpiece rebuilt after the Great Chicago Fire, symbolizing faith and resilience.

20 minutes

Richard H. Driehaus Museum

50 East Erie St, , Chicago, 60611-2730, Illinois

Follow your guide along charming streets lined with architecture from the Gilded Age, stopping by the exquisite Richard H. Driehaus Museum, an ornate mansion reflecting the opulence of the 19th century. Learn fascinating facts about the Tribune Tower, adorned with stones from world monuments, and admire the bright white façade of the Wrigley Building, a striking icon of the city skyline.

20 minutes

DuSable Bridge

333 Michigan Ave, Chicago, IL 60601, USA

As you cross the DuSable Bridge, once a key crossing during Prohibition times, take in panoramic river views while your guide shares captivating tales from Chicago’s tumultuous past.

10 minutes

American Writers Museum

180 N Michigan Ave, 2nd Floor, Chicago, 60601, Illinois

Pass by the American Writers Museum, a tribute to America’s literary legends, and conclude at the grand Millennium Monument in Wrigley Square—an elegant tribute to Chicago’s centennial.

Pass by without stopping

The Chicago Theatre

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

Extend your route beyond the Millennium Monument to include the legendary Chicago Theatre, where dazzling marquees and old-world glamour echo decades of entertainment history.

30 minutes

Marshall Field And Company Building

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

Pause at the historic Marshall Field and Company Building, a marvel of commercial architecture and innovation, then admire the ornate Chicago Cultural Center, home to the world’s largest Tiffany glass dome—a hidden gem few visitors discover.

30 minutes

Cloud Gate

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

Finally, stand before Cloud Gate, affectionately known as “The Bean,” where the city’s skyline bends and dances in polished steel. It’s the perfect finale to a tour that reflects both the timeless grandeur and modern vibrancy of Chicago. Elevate your city experience with the insight and intimacy only a Private Guide can provide.

1 hour