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Best of Chicago Exclusive Private Tour

Explore Chicago’s top sights in just four hours on this private, fully guided tour. Visit Skydeck Chicago for sweeping views from the 103rd floor, take a scenic cruise along the Chicago River to admire the city’s famed architecture, and stop at iconic landmarks like Cloud Gate and Buckingham Fountain. With hotel pick-up, skip-the-line access, and a dedicated guide, this tour blends local insight with effortless convenience offering a thoughtful, relaxed way to experience the highlights of the Windy City.

Key Details
duration
Duration: 4 Hours
guests
Group Size: 10
cancellation
Free cancellation: 100% refund when cancelled at least 24 hours in advance
live tour guide
Live Tour Guide: A guided English tour with convenient round-trip transportation

See what other traveler's have to say about this tour

T
Traci
April 8, 2026
See Sight Tours
5/5
Heidi was a great tour guide—very personable and knowledgeable! She definitely enhanced our time in the Niagara Falls area and gave great recommendations for other things to do.
K
Katrina
February 10, 2026
See Sight Tours
5/5
Manish was great at communicating with us and was very punctual! He offered a great tour.

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Highlights

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Includes

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Excludes

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Description

<p>Book a fully guided and narrated private tour of Chicago - The Windy City with See Sight Tours, Chicago ’s best small-group tours (maximum 7 guests). Enjoy the efficiency and exclusive benefit of having your very own private local expert &amp; guide to share unique stories, local insights &amp; 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 &amp; 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 See Sight 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!</p>

Important Information

Important information for this tour will be added soon.

Our Guest Reviews

1512 reviews for this Tour
T
Traci
April 08, 2026
See Sight Tours
5/5
Heidi was a great tour guide—very personable and knowledgeable! She definitely enhanced our time in the Niagara Falls area and gave great recommendations for other things to do.
K
Katrina
February 10, 2026
See Sight Tours
5/5
Manish was great at communicating with us and was very punctual! He offered a great tour.
P
Priya
March 22, 2026
See Sight Tours
5/5
Niagara-on-the-Lake at the end was the surprise highlight — we never would have found those wineries on our own. Booked the private version for our parents next month.
T
Tomás
March 08, 2026
See Sight Tours
4/5
Great tour, well-paced. The cruise was busy (it always is) but the skip-the-line ticket made all the difference. One star off only because the van air-con struggled on a 30°C day.
M
Megan
February 28, 2026
See Sight Tours
5/5
Booked the night before and they accommodated us with a same-day pickup. The Journey Behind the Falls was the moment of the trip. Bring a waterproof phone case!
R
Robert
February 15, 2026
See Sight Tours
5/5
Third time on a See Sight tour. Same standard every visit — punctual, friendly, knowledgeable. The Whirlpool Aero Car is the best 10 minutes of any Niagara day.

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See Sight Tours
Best of Chicago Exclusive Private Tour - See Sight Tours