• The Peninsula Chicago - Meet your guide outside The Peninsula Chicago, located at 108 E Superior St, Chicago, IL 60611, United States. Please refrain from entering the hotel, as it serves solely as a meeting point and the staff is not briefed about the tour.

• Holy Name Cathedral - Start your journey at the stunning Holy Name Cathedral, a Gothic Revival marvel rebuilt after the Great Chicago Fire, representing faith and resilience.

• Richard H. Driehaus Museum - Stroll with your guide through charming streets adorned with Gilded Age architecture, stopping at the splendid Richard H. Driehaus Museum, an ornate mansion showcasing 19th-century opulence. Discover intriguing details about the Tribune Tower, embellished with stones from global monuments, and admire the bright white façade of the Wrigley Building, a striking symbol of the city skyline.

• DuSable Bridge - As you cross the DuSable Bridge, a significant crossing during Prohibition, enjoy panoramic river views while your guide shares captivating stories from Chicago’s vibrant past.

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

• The Chicago Theatre - Extend your journey beyond the Millennium Monument to include the iconic Chicago Theatre, where dazzling marquees and vintage glamour echo decades of entertainment history.

• Marshall Field And Company Building - 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.

• Cloud Gate - 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 conclusion to a tour that reflects both the timeless grandeur and modern vibrancy of Chicago. Enhance your city experience with the insight and intimacy only a Private Guide can provide.

• 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

• Extended walking route to the Chicago Theatre, Cultural Center, and Cloud Gate (in the 2H option)
• Entry/tickets to any attractions
• Food and drinks

Discover the vibrant essence of Chicago by exploring its renowned landmarks, from the Gothic Holy Name Cathedral to the shining Cloud Gate. Experience untold tales of resilience, art, and innovation. Optionally, visit the Chicago Theatre, Cultural Center, and Tiffany glass dome.

The tour is offered in the following languages:
English
French & Spanish

Select from our outstanding tour options designed to suit your preferences and interests:

2-hour: Downtown
Explore Downtown Chicago to view landmarks such as Holy Name Cathedral, Tribune Tower, and the Wrigley Building. Discover stories of resilience and architectural splendor.

3-hour: Downtown, Chicago Theatre, & Cloud Gate
Explore Downtown Chicago and visit the Chicago Theatre, Cultural Center’s Tiffany dome, and Cloud Gate. Extend your journey through rich history and iconic scenery.

This engaging and history-rich tour will guide you through the architectural marvels and cultural landmarks of Downtown Chicago. With a Licensed Private Guide, you’ll discover the stories behind these iconic sites.

• Please check your email the day before the tour for important details from Rosotravel, your tour operator.
• The itinerary depends on the selected option.
• This is a moderate 1-2 miles walking tour, including some uneven surfaces or steps. The guide will adapt the pace to your group. Wear comfortable shoes and dress for the weather – the tour runs rain or shine!
• To ensure a personalized experience for all guests, our private tours are limited to 25 people per guide. Larger groups will be provided additional guides.
• Entrance tickets, food and drinks are not included in the price, but your guide will gladly recommend attractions and eateries to enhance your visit.
• Have a special request or need accessibility support? Let us know in advance—we’re happy to help!

For a full refund, cancel at least 24 hours before the scheduled departure time.