Chicago River Architecture and History by Private Boat Tour

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Discover Chicago by private boat with a local Chicagoan to highlight its fascinating history and architectural marvels along the way!


  • Board your own private boat for an exclusive tour on the Chicago River!
  • See top Chicago attractions like Willis Tower and Union Station
  • Hear the history of the Chicago River and how it has shaped the city’s identity
  • Explore the Chicago Loop by foot and pass by its architectural marvels
  • Get to know the history of Chicago’s growth from pre-settlement to current day


To understand the city of Chicago, you need to know its river. Hop aboard a private boat with a Windy City local to hear how the Chicago River has shaped the city’s skyline and its very identity, taking in its beautiful architecture from a truly unique perspective! We’ll start with a short walk in the Chicago Loop, where the suits-and-ties speed along on their weekday work commutes. During our own leisurely stroll through the bustling financial and federal district, you’ll learn about several sites of interest, including a turn-of-the-century landmark once the largest store in the world; a neoclassical beauty containing one of the world’s largest Tiffany glass domes; and an iconic venue and its dazzling marquee that has announced top-tier shows since 1921! Once we arrive at the dock after our brief walking tour, you’ll board your very own private boat for a scenic cruise along the Chicago River. Along the way, your tour guide will share stories of the waterway and its historical significance to the city and its people. You’ll pass by the confluence of the north, south, and main branches of the Chicago River, a historic site formerly occupied by Native Americans and later by many of Chicago’s first commercial buildings. As you relax and take in the sights, you’ll spot one of our most innovative skyscrapers, Willis Tower, which held the title of the world’s tallest building for 25 years! Other notable buildings include a vital transit hub featured in many films including The Untouchables and Public Enemies as well as an Art Deco masterpiece so large it once had its own zip code! Once back at the marina, you’ll walk off your boat with plenty of places to explore on foot, with more recommendations from your local guide!


Local guide Private Boat

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