Chicago Private Sightseeing Tours
Private Chicago City Sights Helicopter Tour
Discover all of Chicago’s top sights from great heights on this private helicopter tour.
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$174.50Private City Tour (3-4 hours) - Vehicle, Driver and Guide included!
PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 4 PASSENGERS TOTAL.
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$379Chicago Private 30 Minute Tour For Two
Skim Chicago’s iconic skyline aboard Vertiport Chicago’s all-new two passenger Enstrom 280FX on a 30 Minute Private Tour for 2.
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$770Private 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.
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$660Private 2-hour boat rental aboard New York Style for 8 people ~ Free pizza!
Rent with us and you can take a private, self-guided cruise along the Chicago River where you’re the captain!
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$279Private Chicago Sunset Sail on Lake Michigan
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.
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$439.04Private Custom City Tour in Chicago
Let us put the Custom in Chicago Custom tours… What are your must-see venues?
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$660Chicago Helicopter Pilot Experience
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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$179Private Haunted History of Chicago Ghost Tour
Up for more of a spooky perspective of the Windy City?
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$660Private 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.
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$660Private 2-hour boat rental aboard Deep Dish for 9 people ~ Free pizza!
Rent with us and you can take a private, self-guided cruise along the Chicago River where you’re the captain!
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$299Private Chicago Craft Beer and Pizza Tour
Pair craft beer tastings at three of Chicago's finest breweries with a pizza dinner on these 3-hour tour in the Windy City.
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$9945 Minute Chicago Helicopter Skyline Tour Experience (for 3 passengers)
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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$549Magnificent Mile Photo Shoot and Walking Tour
Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, let us be your personal paparazzi.
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$150Private Chicago Highlights Driving Tour
See Chicago’s most essential landmarks from the comfort of a private vehicle on this 3-hour jaunt around town.
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$992019 Midwest Autumn Colors Excursion
To celebrate the glorious return of autumn, on October 26th and November 2nd we'll head out to superb Matthiessen State Park for an autumn colors hike!
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$36Private 2-hour boat rental aboard Plain Slice for 8 people ~ Free pizza!
Rent with us and you can take a private, self-guided cruise along the Chicago River where you’re the captain!
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$269Chicago Lakefront Electric bike Tour
This tour takes you along the Lakefront bike path.
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$65Museum Campus Photo Shoot and Walking Tour
Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, let us be your personal paparazzi.
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$150Millennium Park Photo Shoot and Walking Tour
Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, let us be your personal paparazzi.
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$150Chicago Riverwalk & History Tour - Self-Guided Walking Tour (iPhone & Android)
Welcome to Chicago’s scenic Riverwalk.
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$2.50