Chicago Skyline Walking Tour and Lake Cruise

Walk beneath Chicago’s soaring skyline, hear its hidden stories, then see it shimmer from the water on a lake cruise. From the iconic Bean to the legendary theatre district, this tour brings the city’s spirit to life—one step and wave at a time.
Discover downtown Chicago on foot with a 5-Star Private Guide leading the way
Cruise Lake Michigan with included tickets and audio commentary onboard
See breathtaking skyline views and snap iconic photos from the water
Learn the city’s best-kept secrets through fascinating stories and history
Get tailored recommendations on top spots to eat, visit, and explore next

Meeting Point

Chicago Athletic Association - The Unbound Collection by Hyatt

12 S Michigan Ave, Chicago, IL 60603, USA

Meet your guide In front of Chicago Athletic Association - The Unbound Collection by Hyatt; 12 S Michigan Ave, Chicago, IL 60603, 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:

• 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

Not included:

• Service tips

What to expect:

Duration: 3 hours

Chicago Athletic Association - The Unbound Collection by Hyatt

12 S Michigan Ave, Chicago, IL 60603, USA

Meet your guide In front of Chicago Athletic Association - The Unbound Collection by Hyatt; 12 S Michigan Ave, Chicago, IL 60603, 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

Cloud Gate

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

Explore Downtown Chicago on a 2-hour private walking tour with tickets for Lake Michigan cruise. Discover downtown Chicago and uncover the stories behind its iconic sights. Start at Cloud Gate—affectionately known as “The Bean”—where your Licensed Guide will share how this shiny steel landmark became a symbol of the city.

50 minutes

Millennium Park

Chicago, Illinois

Walk through Millennium Park to the Millennium Monument, a classical tribute to Chicago’s founders, and pause at the towering Christmas Tree if you're visiting during the festive season.

30 minutes

Marshall Field And Company Building

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

Pass by the Marshall Field and Company Building, once home to one of America’s most luxurious department stores. Your guide will fill you in on its elegant architecture and retail legacy

Pass by without stopping

The Chicago Theatre

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

Then admire the glittering lights of the historic Chicago Theatre and hear how it helped shape the city’s performing arts scene.Then admire the glittering lights of the historic Chicago Theatre and hear how it helped shape the city’s performing arts scene. Nearby, your guide will also introduce the American Writers Museum—an homage to the storytellers who shaped American culture.

30 minutes

Shoreline Sightseeing

401 N Michigan Ave, Chicago, IL 60611, USA

End your walk at the dock for some shoreline sightseeing and set sail on a 45-minute Lake Michigan cruise. Listen to fascinating audio commentary as the city’s skyline unfolds before you. It’s a relaxing way to wrap up your journey and see Chicago from a whole new angle, including landmarks such as the Tribune Tower, the Wrigley Building, and Marina City. There’s no rushing, no crowds—enjoy every moment at your own pace!

1 hour • Admission Ticket Included