Chicago Architecture and Skyline Boat Tour
Discover Iconic Chicago Landmarks on a Private Architecture Cruise with Expert Guide

IL
people
1 participant
hours
- • Explore Chicago's Iconic Landmarks on a Private Tour
- • Enjoy a 4-Hour Guided Experience of Chicago's Skyscrapers
- • Witness the Largest Fountain in the World at Buckingham Fountain
Why We Love This Unique Experience
Discover the beauty and vibrancy of Chicago with the Best of Chicago Small-Group Tour, complemented by an unforgettable Architecture River Cruise. This experience offers a fantastic opportunity to explore the iconic skyline and stunning views of Lake Michigan, all under the guidance of a knowledgeable local expert. With fascinating stories and personalized insights, this tour will unveil the rich history and hidden gems of the Windy City.
The adventure kicks off with convenient hotel pickup in downtown Chicago, ensuring a stress-free start to the day. Begin at the Adler Planetarium Pier, a must-see spot for breathtaking views. Next, embark on a Shoreline Architecture Cruise, where a narrated boat tour showcases over 40 architectural landmarks, revealing both the well-known and lesser-seen features that make Chicago's skyline unique. After the cruise, visit two iconic landmarks, Buckingham Fountain and the famous Chicago Bean, completing a truly immersive Chicago experience.
This small-group tour is not just a remarkable way to explore Chicago; it also makes for a delightful gift! Whether for a birthday, anniversary, or just because, giving the gift of adventure and exploration creates lasting memories. Share the wonder of Chicago's architecture and scenery with someone special today!
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Experience Overview:
Chicago Premium Driving Tour With River Boat CruiseExplore the best of Chicago on an intimate small-group tour with a maximum of 6 guests. Take in the city’s world-famous skyline, bold skyscrapers, and stunning Lake Michigan views while enjoying the expertise of your friendly Tripshepherd guide.
Start your adventure with complimentary downtown Chicago hotel pickup before visiting the Adler Planetarium Pier, one of the most scenic viewpoints of the Windy City.
Next, climb aboard the Shoreline Architecture River Cruise for a narrated boat ride highlighting more than 40 iconic Chicago landmarks. From hidden architectural details to the city’s most recognizable monuments, this cruise offers a unique perspective of Chicago’s skyline and rich history.
To wrap up your Chicago experience, you’ll visit two must-see landmarks: the breathtaking Buckingham Fountain, and Cloud Gate (“The Bean”), one of the most photographed attractions in Millennium Park.
Your day ends with complimentary drop-off at your downtown Chicago hotel!
Meeting Point
238 E Monroe St
238 E Monroe St, Chicago, IL 60601, USA
If you are driving into Downtown Chicago and require parking, we recommend parking in the Millennium Park Garage located, 5 S Columbus Dr, Chicago, IL 60601, United States. It is an underground parking garage where you can park for the duration of your tour.
What's included:
- Complimentary Hotel pickup and drop-off (Downtown Chicago)
- See All Chicago Has to Offer in One Tour
- Small-group tour (6 maximum)
- Chicago Architecture Cruise (Admission Included)
- Narrated Driving Tour of Chicago
Not included:
- Food and Drinks
What to expect:
Duration: 4 hours
Cloud Gate
201 E. Randolph St., Millenium Park, Chicago, 60602, Illinois
We will start our tour with a view of the Cloud Gate also known as the Chicago Bean, British artist Anish Kapoor's first public outdoor work installed in the United States.
15 minutes
Shoreline Sightseeing
401 N Michigan Ave, Chicago, IL 60611, USA
Chicago’s famous architecture! There’s nothing like seeing these world-famous skyscrapers from the Chicago River. Aboard the Shoreline Architecture Cruise, you will enjoy a narrated boat ride where you will see over 40 Chicago landmarks, from hidden architectural treasures to the city’s most famous monuments.
1 hour, 15 minutes • Admission Ticket Included
Clarence F. Buckingham Fountain
301 S. Columbus Dr, Grant Park, Chicago, 60605, Illinois
Buckingham Fountain is a Chicago Landmark in the center of Grant Park, and between Queen's Landing and Congress Parkway. Dedicated in 1927, it is one of the largest fountains in the world.
15 minutes
Adler Planetarium
1300 S. DuSable Lake Shore Dr., , Chicago, 60605-2489, Illinois
The Adler view point, is the best spot to take a photo of the Chicago Skyline.
Please note, from June 18th to August 13th we cannot guarantee the stops Buckingham Fountain and Adler viewpoint. If we cannot visit those stops, we will substitute with a luxurious drive up Chicago's famed Magnificient Mile; including hop-out stops at The Chicago Theatre, the electric and unnamed Chicago Picasso sculpture in Daley Plaza, and the Chicago Watertower (sole survivor of the Chicago Fire).
15 minutes
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Details & Important Info
Additional Experience Details & Important Information
Wheelchair accessible
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Transportation options are wheelchair accessible
Suitable for all physical fitness levels
Cancellations & Refunds
Reservation Changes, Cancellations & Refunds
Changes to reservations for tickets can be made until 3 days prior to the date scheduled. Reservations may be re-scheduled by the operator of the activity due to reasons such as weather, minimum participation requirements, mechanical issues or other interruptions beyond their control.
Organized by
Tripshepherd USA
Product SKU: US-3613-0034
Google Business Profile: See Sight Tours - Niagara Falls Tours USA
Chicago Architectural River Cruise and Landmarks
IL
people
1 participant
hours
- • Explore Chicago's Iconic Landmarks on a Private Tour
- • Enjoy a 4-Hour Guided Experience of Chicago's Skyscrapers
- • Witness the Largest Fountain in the World at Buckingham Fountain
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