Chicago Architecture and Skyline Boat Tour

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!

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