Top Chicago Private Sightseeing Tours

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Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
2
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...
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2 hours Instant Confirmation
from
$427.28
Details
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$427.28
Details
Private Sightseeing Cruise in Chicago
What an amazing experience you will have on this One of a Kind Private Sightseeing tour! We will explore the wonders of Chicago from a...
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4 hours
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$1,750
Details
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$1,750
Details
Private Al Capone Gangster Tour in Chicago
2
Chicago and the history of the mob are synonymous when we look back at history. That’s why we provide an in-depth Chicago Gangster Tour that...
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3 hours Hotel pickup offered Instant Confirmation
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$330
Details
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$330
Details
Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
5
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...
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2 hours Instant Confirmation
from
$427.28
Details
from
$427.28
Details
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...
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3 hours Hotel pickup offered Instant Confirmation
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$330
Details
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$330
Details
Chicago Private Tours
3
PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 4 PASSENGERS TOTAL. Thank you for contacting Chicago Private Tours! We would love to help...
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3 to 4 hours Hotel pickup offered Instant Confirmation
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$425.34
Details
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$425.34
Details
Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket
The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2 to...
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120 to 150 minutes Instant Confirmation
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$153.70
Details
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$153.70
Details
Learn to Fly a Helicopter: Chicago Helicopter Pilot Intro Flight
This experience is as unique as it gets, as you will be allowed to take to the controls and see just what it takes to...
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30 minutes Instant Confirmation
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$193.85
Details
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$193.85
Details
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...
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3 hours Hotel pickup offered Instant Confirmation
from
$330
Details
from
$330
Details
Private Chicago Architecture Tour
3
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...
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3 hours Hotel pickup offered Instant Confirmation
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$660
Details
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$660
Details
Private Secret Food Tour of Chicago
We are Chi-Town foodies of the first order, and we're so excited to share with you all the culinary delights this historic Midwestern city has...
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3 hours
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$103.36
Details
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$103.36
Details
Chicago Lakefront Electric Bike Tour
This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will...
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1 to 2 hours Instant Confirmation
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$69.34
Details
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$69.34
Details
Private Half Day Highlights of Chicago Tour with 360 Chicago Observation Deck
Discover the compelling character of America’s third-largest city, renowned for its jazz-and-blues heritage, striking architecture, historic streets and fine array of public art.On your Private...
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4 hours Instant Confirmation
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$270
Details
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$270
Details
Shoot My Travel- Experience Chicago With a Local Photographer
1
Chicago is the perfect city to get a dose of all that is great about America: beautiful parks, innovative architecture, and historic figures. All with...
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1 hour Instant Confirmation
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$250.67
Details
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$250.67
Details
Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago
1
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...
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2 hours Hotel pickup offered
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$200
Details
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$200
Details
Chicago Riverwalk Self-Guided Walking Tour
Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city second Lakefront', the Riverwalk contains restaurants during the summer...
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1 to 2 hours Instant Confirmation
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$6
Details
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$6
Details
Discovering Vintage Chicago: The Loop Walking Audio Tour by VoiceMap
1
Amy Bizzarri, author of Discovering Vintage Chicago and 111 Places in Chicago That You Must Not Miss will take you on a fascinating journey to...
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50 minutes Instant Confirmation
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$5.34
Details
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$5.34
Details
Private Exploration Game of Eastside Chicago
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...
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1 hour 35 minutes Instant Confirmation
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$3.91
Details
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$3.91
Details
Personal Travel and Vacation Photographer Tour in Chicago
No more selfies or pestering strangers for photos of yourself and loved ones, enjoy the services of a professional vacation photographer in Chicago to capture your...
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1 to 3 hours Instant Confirmation
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$312.25
Details
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$312.25
Details
Millennium Park Photo Shoot and Walking Tour
1
Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us. You...
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30 to 120 minutes Instant Confirmation
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$150
Details
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$150
Details
Private 45-Minute Chicago Skyline Helicopter Tour
8
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...
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45 minutes Instant Confirmation
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$849
Details
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$849
Details

Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What are the best options for Chicago Private Sightseeing Tours?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best Chicago Private Sightseeing Tours are:

Q: What Chicago Private Sightseeing Tours are taking additional safety precautions?

A: The following activities in Chicago experiences are providing additional COVID-19 safety measures (to read the specific policies please click the activity name and read the "Keeping you safe during COVID-19" section located underneath the booking calendar):

Top Chicago Private Sightseeing Tours

Chicago Tours

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Nearby

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

Private Sightseeing Cruise in Chicago

Private Al Capone Gangster Tour in Chicago

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

Private Custom City Tour in Chicago

Chicago Private Tours

Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket

Learn to Fly a Helicopter: Chicago Helicopter Pilot Intro Flight

Private Speakeasy Pub Crawl in Chicago with Local Historian

Private Chicago Architecture Tour

Private Secret Food Tour of Chicago

Chicago Lakefront Electric Bike Tour

Private Half Day Highlights of Chicago Tour with 360 Chicago Observation Deck

Shoot My Travel- Experience Chicago With a Local Photographer

Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

Chicago Riverwalk Self-Guided Walking Tour

Discovering Vintage Chicago: The Loop Walking Audio Tour by VoiceMap

Private Exploration Game of Eastside Chicago

Personal Travel and Vacation Photographer Tour in Chicago

Millennium Park Photo Shoot and Walking Tour

Private 45-Minute Chicago Skyline Helicopter Tour

Frequently Asked Questions

Q: What are the best options for Chicago Private Sightseeing Tours?

Q: What Chicago Private Sightseeing Tours are taking additional safety precautions?