Private Sightseeing Tours in Chicago
Top 10 Best Chicago Private Sightseeing Tours
Found 83 Private Sightseeing Tours activities in Chicago. Sort by Popularity. - Page 2Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline... More
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Chicago Private Sunset Sail on Lake Michigan
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline... More
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Private Speakeasy Pub Crawl in Chicago with Local Historian
Our Prohibition Era Speakeasy Pub Crawl is filled with cocktails and a perfect venue for bachelor or bachelorette parties, corporate events, or just a fun night out on the town to celebrate life and your friends. Hosted by a local... More
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Chicago in a Day: Food and Architecture Private Walking Tour
Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish! Our two-part tour begins by exploring the heart of downtown Chicago - with its iconic architect... More
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Private Chicago Guided Tour with Hotel Pickup
One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour guide take you around the most important sites and locations of Chicago. Being a private tour, stop... More
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Private Chicago Architecture Tour
Despite the Great Fire that once ravaged the city of Chicago over a century ago, the city is credited as the birthplace of the modern skyscraper. Chicago is so renowned for architecture that it’s the most vertical metropolis fro... More
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Art Institute of Chicago Private Expert Guided Tour
Let our expert local guides share their passion with you for The Art Institute of Chicago on this private 2 hour tour. As you traverse the hallowed halls, you’ll discover an extraordinary collection spanning centuries and cultur... More
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Best of Chicago: Architecture & Highlights City Private Tour
Get the best of Chicago with a local guide on this walking tour featuring the city’s best neighborhoods, top attractions, and the Chicago ‘L’! We’ll start by exploring the Chicago Loop, home to an array of mind-blowing ar... More
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Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck
On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hancock Tower. Your guide is a local who has plenty of tales about Chicag... More
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Chicago Neighborhood Food Private Walking Tour
This Chicago food tour gives you the chance to explore the city’s foodie scene to its fullest. Explore legendary bakeries in neighborhoods around the city. You'll discover Chicago’s immigrant roots with incredible food from ar... More
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Chicago Private Foodie Tour: Windy City Faves
Our Chicago Foodie Lovers Tour will take you to the most iconic and delicious spots in Chicago all in one day. If you are looking for a little bit of culture, great photos, and a ton of delicious food then this is the tour for you... More
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Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago
Enjoy a private 2-hour walking tour with Belgian-American tour guide Leentje. She will introduce you to the city she calls home since 2014. Every tour is different and custom-made. Tours are available in English, French, or Dutch.... More
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Private Chicago Highlights Driving Tour
See Chicago’s most essential landmarks from the comfort of a private vehicle on this 3-hour jaunt around town. Your guide will pick you up directly from your Chicago accommodation, after which you’ll be whisked away to see the... More
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Chicago 2-Hour Sightseeing Transfer by Luxury Stretch Limo
Choose the number of hours and we can help you make the most out of your time! Book a VIP treatment to see the city in your private car. Our knowledgeable drivers will do the hard work so that you an enjoy the view. Limo service H... More
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Luxury SUV 4-Hours Sightseeing Tour in Chicago DT Hourly Service
Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking parks, the famous Cloud Gate (The Bean), world-class museums, and reno... More
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Private Haunted History of Chicago Ghost Tour
Up for more of a spooky perspective of the Windy City? Boy, does it deliver. We have curated a unique and underground ghost tour, providing you with the rare opportunity to visit many of Chicago’s notable haunted locations. â... More
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Private Chicago 6-Hour Boat Tour with Captain
Our Mission: We are dedicated to curating exceptional boating experiences, offering day and night cruises, fireworks displays, and serene voyages along the Chicago River. Our goal is to share the magic of the city's waterways, ble... More
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Private Custom City Tour in Chicago
Let us put the Custom in Chicago Custom Tours. What are your must-see venues? What would personalize your excursion? We’ll plan your tour and make it happen, and also provide suggestions based on your interests.... More
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