Private Tour of Chicago

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Highlights

VIP Private small group tour
VIP Transportation for your exclusive enjoyment
Transportation in a complimentary vehicle
Private Tour Guide for exclusive fully narrated tour
Complimentary downtown hotel private pick up and drop off

Summary

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 .

Tour info

Duration

4 hours

Group Size

Pricing (From)

Private Tour of Chicago: (018-9964 years)

$1,129.00

Why take this tour?

Book a fully guided and narrated private tour of Chicago - The Windy City with Tripshepherd Tours, 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 a private, complimentary vehicle 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 as well as stay hydrated and fueled with a light snack and spring water.

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 Tour 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!

What’s included?

VIP Private small group tour
VIP Transportation for your exclusive enjoyment
Transportation in a complimentary vehicle
Private Tour Guide for exclusive fully narrated tour
Complimentary downtown hotel private pick up and drop off
Complimentary spring water and a light snack
All Attraction admissions, taxes and fees included
Skydeck Chicago - Observatory and The Ledge
Chicago Bean (Cloud Gate)
Architectural Sightseeing Cruise
Chicago Adler view point
Chicago Buckingham Fountain
Gratuities (optional)

Things to know

Before you book

Complimentary hotel pick up and drop off in downtown Chicago
Attractions are not private
Maximum 7 guests

Before you go

Operates in all weather conditions, please dress appropriately
A moderate amount of walking is involved
Pick up time will be confirmed 1-3 days prior to the tour date via email or phone. If you do not have access to these, please be ready 30 minutes prior to tour start time in the hotel lobby.

Cancellation Policy

Full refunds will be offered for cancellations made at least 24 hours prior to departure time. For cancellations made with less than 24 hours to departure time, a $50 cancellation fee per guest will apply.

Operator Website

Operated by:

About operator:

Tripshepherd specializes in offering intimate small-group tours across popular destinations in North America. Our commitment to small-group dynamics ensures a more personal connection, greater flexibility, and an escape from the hassle of crowded buses and the need for microphones. At the heart of our tours are local experiences; we proudly hire local guides to support community growth, create jobs, and provide our guests with an authentic glimpse into each destination. Our friendly guides are dedicated to connecting personally with each guest, ensuring a caring and memorable experience. With Tripshepherd, every journey is not just a tour, but a unique story woven into the fabric of local life, guaranteeing an authentic, personal, and local adventure.