Available languages
4 hours
Mobile ticket
Explore 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!
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
For a full refund, cancel at least 24 hours before the scheduled departure time.
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
Food and Drinks
Gratuities
Select a pickup point
Cloud Gate
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.
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.
Pickup included
163 reviews
Total reviews and rating from Viator & Tripadvisor
Chris M,
Jun 16, 2025
- Viator
This was a fantastic way to “do” Chicago! Jack was very personable and accommodating. It is obvious that he loves his city, and he is very knowledgeable in the things that make Chicago great. The activities included in this tour really set it apart as well. The tour company chose the best and took care of all the details including checking us in at the venues. My wife, teenage daughters, and I had a great time, and we highly recommend this tour.
Matthew B,
Jun 8, 2025
- Viator
Excellent Tour!!! Very knowledgeable and informative tour of Chicago- especially the Batman Trivia and sights!!! Excellent tour guides with Jack and Pam! My family loved it!!!
Sheena D,
Feb 1, 2025
- Viator
Amazing city tour! Knowledgeable guide, great sights, and friendly services. Our tour guide Robert was great! Highly recommend for an unforgettable experience!
Lanie C,
Oct 11, 2024
- Viator
I highly recommend this tour. Our tour guide - Tony came on time. He is knowledgeable and accommodating. Amazing architecture and views of the places we visited. We really enjoyed this tour. Great tour.
Sandra E,
Oct 8, 2024
- Viator
The tour was absolutely wonderful. The tour guide/driver was knowledgeable, friendly and customer service oriented. Tour was well planned and covered all the key places.
Operated by See Sight Tours USA