Private Tour of Chicago

Book a fully guided and narrated private tour of Chicago - The Windy City with Tripshepherd, Chicago ’s best small-group tours (maximum 7 guests). Enjoy the efficiency and exclusive benefit of having your very own private local expert & guide to share unique stories, local insights & highlights as well as offering you personalized recommendations tailored to your groups interest in Chicago .

You and your private small group will enjoy complimentary downtown Chicago hotel pick up in the comfort and style of one of our complimentary vehicles to journey throughout the city, experiencing the city’s top attractions and visitor experiences along with several famous points of interest.

Includes fully guided and narrated private tour, skip the ticket line entry & all attraction admission fees.

Your exclusive, private tour will begin with your very own local guide greeting you at your downtown Chicago hotel.

To begin your tour your Tripshepherd guide will take you to the tallest building in the Western Hemisphere - Skydeck Chicago (formerly Sears Tower). Taking the elevator all the way up to the 103rd floor where you will enjoy a spectacular 360-degree view spanning 50 miles and 4 states. The most spectacular view - 1,353 feet down "Dare to Stand Out" on The Ledge - special glass balconies extending 4.3 feet outside the building which provides a thrilling, once-in-a-lifetime experience.

Next, once your feet are back on solid ground your guide will take you to the Adler Planetarium Pier, a must-stop while in the Windy City. As the mecca for American architects, Chicago’s skyline is one of the greatest and this viewpoint is the best place to marvel at the skyline Lake Michigan. Your guide will then take you to see the beauty of Chicago's architecture by seeing world-famous skyscrapers from the Chicago River. Aboard the Shoreline Architecture Cruise you will enjoy a narrated boat tour where you will see the breathtaking views of over 40 Chicago iconic landmarks, from hidden architectural features to the Windy City's most famous monuments. To finish your exclusive, private tour, you will get to visit two iconic Chicago landmarks - the Buckingham Fountain, one the largest fountains in the world and the Chicago Bean (Cloud Gate) - British artist Anish Kapoor's first public outdoor work installed in the United States - both great locations to take great pictures.

Enjoy complimentary downtown Chicago drop off in the comfort of one of our complimentary vehicles at the end of your tour.

Experience the best of Chicago - the Windy City in an exclusive, private tour and reserve a spot with us today!