Private Sightseeing Tours in Chicago
Top 10 Best Chicago Private Sightseeing Tours
Found 84 Private Sightseeing Tours activities in Chicago. Sort by Popularity.Private 45-Minute Chicago Skyline Helicopter Tour
This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the city of Chicago on a 45 minute thrill seeking guided tour. The price is... More
Private Tour
![Private 45-Minute Chicago Skyline Helicopter Tour Private 45-Minute Chicago Skyline Helicopter Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0c/02/6d/0b.jpg)
Private 45-Minute Chicago Skyline Helicopter Tour
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Chicago
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Superb114 reviews4.8
This tour is unique as it offers the ability for you and two of your friends or family (a total of 3....
Private Tour
Private 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
Private Tour
![Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/9a/56/a8.jpg)
Private Lake Michigan Sailing Charter and Sightseeing Tour of Chi....
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Chicago
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Superb60 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Private Tour
![Art Institute of Chicago Skip-the-Line Guided Museum Tour Art Institute of Chicago Skip-the-Line Guided Museum Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/10/09/77/d8.jpg)
Art Institute of Chicago Skip-the-Line Guided Museum Tour
The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour exclusive guided museum tour, you’ll be able to skip the line and explore it’s mo... More
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![Art Institute of Chicago Skip-the-Line Guided Museum Tour Art Institute of Chicago Skip-the-Line Guided Museum Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/10/09/77/d8.jpg)
Art Institute of Chicago Skip-the-Line Guided Museum Tour
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Chicago
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Superb169 reviews5
The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Me....
Free Cancellation
Private Tour
(Saving 20% )
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
Private Tour
![Chicago Private Sunset Sail on Lake Michigan Chicago Private Sunset Sail on Lake Michigan](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0b/b1/bf/a0.jpg)
Chicago Private Sunset Sail on Lake Michigan
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Chicago
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Superb23 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Private Tour
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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Private Tour
![Private Speakeasy Pub Crawl in Chicago with Local Historian Private Speakeasy Pub Crawl in Chicago with Local Historian](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/06/81/90/82.jpg)
Private Speakeasy Pub Crawl in Chicago with Local Historian
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Chicago
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Superb7 reviews4.7
Our Prohibition Era Speakeasy Pub Crawl is filled with cocktails and a perfect venue for bachelor or....
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Private Tour
Private Chicago Scenic Driving Tour
Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic Driving Tour wi... More
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![Private Chicago Scenic Driving Tour Private Chicago Scenic Driving Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0b/e8/50/77.jpg)
Private Chicago Scenic Driving Tour
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Chicago
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Superb10 reviews5
Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires ....
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Private Tour
Chicago Private Custom City Tour with Hotel Pick Up
PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS. Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago. Our services include pick up from your downtown Chicago hotel, a 3-4... More
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Private Tour
![Chicago Private Custom City Tour with Hotel Pick Up Chicago Private Custom City Tour with Hotel Pick Up](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0b/ca/1f/94.jpg)
Chicago Private Custom City Tour with Hotel Pick Up
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Chicago
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Superb187 reviews4.9
PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS. Thank you for contacting Chicago Privat....
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Private Tour
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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Private Tour
![Art Institute of Chicago Private Expert Guided Tour Art Institute of Chicago Private Expert Guided Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/12/54/36/13.jpg)
Art Institute of Chicago Private Expert Guided Tour
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Chicago
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Superb35 reviews5
Let our expert local guides share their passion with you for The Art Institute of Chicago on this pr....
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Private Tour
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 Tour
![Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/08/8a/ea/2c.jpg)
Your Way or the Highway: 2-hour Customized Private Walking Tour i....
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Chicago
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Superb32 reviews5
Enjoy a private 2-hour walking tour with Belgian-American tour guide Leentje. She will introduce you....
Skip The Line
Private Tour
Private Evening Sail in Chicago Ending with Navy Pier Fireworks
Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Navy Pier fireworks. Over the course of two hours, you’ll sail along Chicago’s beautiful lakefront with a view of the city skyli... More
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![Private Evening Sail in Chicago Ending with Navy Pier Fireworks Private Evening Sail in Chicago Ending with Navy Pier Fireworks](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/06/6c/6b/c8.jpg)
Private Evening Sail in Chicago Ending with Navy Pier Fireworks
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Chicago
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Superb7 reviews5
Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Na....
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Private Tour
Insta Walk and Polaroid Photoshoot in Chicago
Discover a new side of Chicago with Insta Walk! I offer stylish photos, cool angles, and creative ideas during our relaxed and friendly stroll. I'll use both iPhone and Polaroid cameras to capture your best shots. You'll get abou... More
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Private Tour
![Insta Walk and Polaroid Photoshoot in Chicago Insta Walk and Polaroid Photoshoot in Chicago](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/12/27/06/b1.jpg)
Insta Walk and Polaroid Photoshoot in Chicago
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Chicago
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Superb7 reviews5
Discover a new side of Chicago with Insta Walk! I offer stylish photos, cool angles, and creative id....
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Private Tour
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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![Best of Chicago: Architecture & Highlights City Private Tour Best of Chicago: Architecture & Highlights City Private Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0b/a5/24/c4.jpg)
Best of Chicago: Architecture & Highlights City Private Tour
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Chicago
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Superb93 reviews4.9
Get the best of Chicago with a local guide on this walking tour featuring the city’s best neighbor....
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Private Tour
Dragon Kings Quest Experience in Chinatown Chicago
Get ready to explore Chicago Chinatown landmarks, hotspots, and popular restaurants all while playing the role of a brave Imperial Advisor to the Emperor of China. As you solve challenges, the story unfolds and exact directions ... More
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![Dragon Kings Quest Experience in Chinatown Chicago Dragon Kings Quest Experience in Chinatown Chicago](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/12/20/1e/0d.jpg)
Dragon Kings Quest Experience in Chinatown Chicago
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Chicago
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Very Good4 reviews3.8
Get ready to explore Chicago Chinatown landmarks, hotspots, and popular restaurants all while playin....
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Chicago Deep Dish Pizza Self-Guided Tour
Take a deep dive into a deliriously delicious world, where lofty, flaky crusts brim with sweet tomato sauce and a brazen amount of melty, gooey cheese. No trip to Chicago is complete without indulging in its most iconic and origin... More
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![Chicago Deep Dish Pizza Self-Guided Tour Chicago Deep Dish Pizza Self-Guided Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0b/c7/4e/4a.jpg)
Chicago Deep Dish Pizza Self-Guided Tour
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Chicago
Take a deep dive into a deliriously delicious world, where lofty, flaky crusts brim with sweet tomat....
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Private Tour
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 Neighborhood Food Private Walking Tour Chicago Neighborhood Food Private Walking Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/10/7a/c1/fa.jpg)
Chicago Neighborhood Food Private Walking Tour
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Chicago
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Superb19 reviews4.9
This Chicago food tour gives you the chance to explore the city’s foodie scene to its fullest. Exp....
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Private Tour
![Chicago Millennium Park Self-Guided Walking Tour Chicago Millennium Park Self-Guided Walking Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0f/3a/f0/21.jpg)
Chicago Millennium Park Self-Guided Walking Tour
Enjoy moving at your own pace through Chicago's Millennium Park with an app as your guide. You and your private party can stop or start the app whenever you like; pausing to explore further on your own. Take in the sights of the p... More
Free Cancellation
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![Chicago Millennium Park Self-Guided Walking Tour Chicago Millennium Park Self-Guided Walking Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0f/3a/f0/21.jpg)
Chicago Millennium Park Self-Guided Walking Tour
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Chicago
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Exellent4 reviews4.5
Enjoy moving at your own pace through Chicago's Millennium Park with an app as your guide. You and y....
Free Cancellation
Skip The Line
Private Tour
(Saving 10% )
The Loop, River North and Chicago’s Theater District: A Self-Guided Audio Tour
Are you looking for a way to see Chicago without joining a tour group? Explore at your own pace with this affordable walking tour. • Take in Chicago’s concrete giants and hear fascinating stories about quirky artworks, local ... More
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![The Loop, River North and Chicago’s Theater District: A Self-Guided Audio Tour The Loop, River North and Chicago’s Theater District: A Self-Guided Audio Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0e/95/e1/ea.jpg)
The Loop, River North and Chicago’s Theater District: A Self-Gu....
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Chicago
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Exellent4 reviews4.5
Are you looking for a way to see Chicago without joining a tour group? Explore at your own pace with....
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Private Tour
Michigan Avenue Rendezvous Mobile App Self-Guided Walking Tour
Venture along Michigan Avenue on an interactive tour to uncover Chicago's hidden gems and iconic landmarks. Dive into the city's rich history, answer trivia, and complete challenges for a unique experience blending sightseeing wit... More
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![Michigan Avenue Rendezvous Mobile App Self-Guided Walking Tour Michigan Avenue Rendezvous Mobile App Self-Guided Walking Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/13/2c/53/43.jpg)
Michigan Avenue Rendezvous Mobile App Self-Guided Walking Tour
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Chicago
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Exellent4 reviews4.5
Venture along Michigan Avenue on an interactive tour to uncover Chicago's hidden gems and iconic lan....
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Private Tour
![Chicago Quest Experience: The Heist Chicago Quest Experience: The Heist](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0e/49/57/a5.jpg)
Chicago Quest Experience: The Heist
Play a city game where you will follow clues to discover amazing places and local stories in Chicago. You’ll tour Chicago’s famous Millenium Park and learn about the iconic works of art that populate the area on your way to r... More
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![Chicago Quest Experience: The Heist Chicago Quest Experience: The Heist](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0e/49/57/a5.jpg)
Chicago Quest Experience: The Heist
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Chicago
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Very Good8 reviews3.8
Play a city game where you will follow clues to discover amazing places and local stories in Chicago....
Free Cancellation
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(Saving 20% )
Haunted Quest Experience in Chicago
Discover Chicago’s haunted locations by following clues and solving puzzles on your phone. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. Ready for an adventure... More
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![Haunted Quest Experience in Chicago Haunted Quest Experience in Chicago](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0e/a5/25/af.jpg)
Haunted Quest Experience in Chicago
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Chicago
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Very Good5 reviews3.8
Discover Chicago’s haunted locations by following clues and solving puzzles on your phone. As you ....
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Private Tour