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Offered languages
- English
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.
Highlights:
• 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
Did you know there’s a sculpture in Chicago that reflects the whole skyline? With Rosotravel’s private tour, you'll walk through the city’s most iconic spots, then see it all again from the water on a relaxing lake cruise. It's a fun, personal way to experience the best of Chicago in just a few hours.Reserve your spot ow!
What's Included
Meeting and pickup
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.
Itinerary
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1
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 • Admission ticket free -
2Cloud Gate
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 • Admission ticket free -
3Millennium Park
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 • Admission ticket free -
(Pass by)
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
Admission ticket free -
4The Chicago Theatre
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 • Admission ticket free -
5
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
Additional info
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Infants are required to sit on an adult’s lap
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
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Additional info
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Infants are required to sit on an adult’s lap
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Suitable for all physical fitness levels
- 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!
Tags
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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Cancellation Policy
- For a full refund, you must cancel at least 24 hours before the experience’s start time.
- If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the experience’s start time will not be accepted.
You can cancel up to 24 hours in advance of the experience for a full refund.
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