Explore Chicago’s skyline and secrets on a private walking tour and lake cruise. Discover hidden stories and capture stunning views.
Explore Chicago’s skyline and secrets on a private walking tour and lake cruise. Discover hidden stories and capture stunning views.
- Chicago Athletic Association - The Unbound Collection by Hyatt - Meet your guide outside the Chicago Athletic Association - The Unbound Collection by Hyatt; 12 S Michigan Ave, Chicago, IL 60603, 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.
- Cloud Gate…
- Chicago Athletic Association - The Unbound Collection by Hyatt - Meet your guide outside the Chicago Athletic Association - The Unbound Collection by Hyatt; 12 S Michigan Ave, Chicago, IL 60603, 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.
- Cloud Gate - Embark on a 2-hour private walking tour of Downtown Chicago, complete with tickets for a Lake Michigan cruise. Discover the heart of Chicago and learn the stories behind its famous landmarks. Begin at Cloud Gate—fondly known as “The Bean”—where your Licensed Guide will explain how this gleaming steel sculpture became a city icon.
- Millennium Park - Stroll through Millennium Park to the Millennium Monument, a classical homage to Chicago’s founders, and take a moment at the towering Christmas Tree if visiting during the holiday season.
- Marshall Field And Company Building - Walk past the Marshall Field and Company Building, once the site of one of America’s most opulent department stores. Your guide will share insights into its sophisticated architecture and retail history.
- The Chicago Theatre - Next, admire the sparkling lights of the historic Chicago Theatre and learn about its influence on the city’s performing arts scene. Nearby, your guide will also introduce the American Writers Museum—a tribute to the authors who shaped American culture.
- Shoreline Sightseeing - Conclude your walk at the dock for some shoreline sightseeing and embark on a 45-minute Lake Michigan cruise. Enjoy captivating audio commentary as the city’s skyline unfolds before you. It’s a serene way to conclude your journey and view Chicago from a fresh perspective, including landmarks such as the Tribune Tower, the Wrigley Building, and Marina City. There’s no rush, no crowds—savor every moment at your leisure!

- Personalized tips on the best places to visit, eat, and explore
- 5-Star Licensed Guide fluent in your chosen language
- Private Walking Tour of Downtown Chicago with a Lake Michigan Cruise
- Tickets for a 45-minute Lake Michigan Cruise with skyline views and audio commentary
- Engaging stories about Chicago’s history, architecture, and culture
- Personalized tips on the best places to visit, eat, and explore
- 5-Star Licensed Guide fluent in your chosen language
- Private Walking Tour of Downtown Chicago with a Lake Michigan Cruise
- Tickets for a 45-minute Lake Michigan Cruise with skyline views and audio commentary
- Engaging stories about Chicago’s history, architecture, and culture
- Tickets to attractions
- Food and drinks
- Tickets to attractions
- Food and drinks
Stroll under Chicago’s impressive skyline, uncover its hidden tales, and admire its beauty from the water on a lake cruise. From the famous Bean to the renowned theatre district, this tour captures the essence of the city—step by step and wave by wave.
Highlights:
• Explore downtown Chicago on foot with a 5-Star Private Guide
• Enjoy a Lake Michigan…
Stroll under Chicago’s impressive skyline, uncover its hidden tales, and admire its beauty from the water on a lake cruise. From the famous Bean to the renowned theatre district, this tour captures the essence of the city—step by step and wave by wave.
Highlights:
• Explore downtown Chicago on foot with a 5-Star Private Guide
• Enjoy a Lake Michigan cruise with tickets and onboard audio commentary included
• Capture stunning skyline views and take iconic photos from the water
• Discover the city’s best-kept secrets through engaging stories and history
• Receive personalized recommendations on top dining, attractions, and exploration spots
Did you know there’s a sculpture in Chicago that mirrors the entire skyline? With Rosotravel’s private tour, you’ll explore the city’s most iconic locations, then view it all again from the water on a leisurely lake cruise. It’s an enjoyable, personalized way to experience the best of Chicago in just a few hours. Reserve your spot now!
- Please check your email the day before the tour for important details from Rosotravel, your tour operator.
- This tour includes a 45-minute sightseeing cruise—please arrive on time for smooth boarding.
- Your Private Guide will escort you to the dock and provide all information but will not join you on the cruise.
- Audio commentary is available in English aboard the cruise, Please bring a valid photo ID or passport.
- This is a moderate walking tour covering 2 km with some uneven surfaces and steps. Your guide will adapt the pace to your group.
- Please wear comfortable shoes and dress appropriately—the tour runs rain or shine!
- 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.
For a full refund, cancel at least 24 hours before the scheduled departure time.