Chicago Premium Driving Tour with River Boat Cruise
Overview
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!
Additional Info
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
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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
Food and Drinks
Gratuities
Meeting and Pickup
Pickup points
Select a pickup point
What To Expect
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.
Options
Chicago Premium Driving Tour with River Boat Cruise
Pickup included
Reviews
164 reviews
Total reviews and rating from Viator & Tripadvisor
Tony was amazing and full...
Johnnie Q,
Oct 25, 2025
- Review from Viator
5.00Tony was amazing and full of information.We had an awesome time and Tony kept us laughing throughout the tour.
Doing Chicago
Chris M,
Jun 16, 2025
- Review from Viator
5.00This 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.
Impressive Tour!!!
Matthew B,
Jun 8, 2025
- Review from Viator
5.00Excellent 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!!!
Amazing city tour!...
Sheena D,
Feb 1, 2025
- Review from Viator
5.00Amazing city tour! Knowledgeable guide, great sights, and friendly services. Our tour guide Robert was great! Highly recommend for an unforgettable experience!
Wonderful Experience
Lanie C,
Oct 11, 2024
- Review from Viator
5.00I 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.
Excellent all around.
Sandra E,
Oct 8, 2024
- Review from Viator
5.00The 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.
Best tour ever!
sstanding,
Sep 26, 2024
- Review from Tripadvisor
5.00Robert was the hands down the best tour guide we have ever had. He was professional, pleasant, and knowledgeable about the city. Everything was lined up for us, including tickets to the observation deck of the Willis (Sears) Tower, and the architectural boat tour. He accompanied us right through the check-in process. I would take this tour again in a heartbeat.
Great tour for 1st timers
Kimberly L,
Aug 31, 2024
- Review from Viator
5.00It was great! Our first time to Chicago. Lots of good information, plenty of time for pictures at the stops. Great views from Willis tower. The architecture tour was amazing. 10/10 recommend!
Robert was a fantastic...
Jen W,
Aug 21, 2024
- Review from Viator
5.00Robert was a fantastic guide, and this exceeded our expectations. This was a lot of fun, it's a great activity to do as a couple...my wife and I really really enjoyed this.
Expensive and not a good trip
claudia g,
Jul 26, 2024
- Review from Viator
2.00We were extremely disappointed could not see any of the sights because we were 3 people in the backseat and did not fit.into the small car. We had to rush through the Willis Tower so we could make the boat cruise standing in line for all we paid $1,000 and could have done the hop on hop off for $200 and actually would have been able to see the the sights our tour guide was nice and knowledgeable but was worst trip ever
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Operated by See Sight Tours USA