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!