Top Chicago Private Sightseeing Tours

Let us put the Custom in Chicago Custom tours… What are your must-see venues?
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PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 4 PASSENGERS TOTAL.
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Chicago and the history of the mob are synonymous when we look back at history.
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Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.
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Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.
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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.
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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.
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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.
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Up for more of a spooky perspective of the Windy City?
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See Chicago’s most essential landmarks from the comfort of a private vehicle on this 3-hour jaunt around town.
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Please note: Chicago's reopening plan requires that we limit capacity on all boats to 4 adults and 2 children (6 total).
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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 fly a helicopter!
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Chicago Premium Outlets is the premier shopping destination in the Chicago metro area.
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Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us.
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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 travels in a contemporary and candid style.
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Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us.
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Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us.
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This tour takes you along the Lakefront bike path.
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Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us.
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Please note: Chicago's reopening plan requires that we limit capacity on all boats to 4 adults and 2 children (6 total).
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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 the timeless, classic spots that evoke the unique character of Chicago's Loop.
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