Embark on a captivating journey through Chicago’s most illustrious addresses, where each step tells a story of architectural brilliance, historical grandeur, and cultural allure. From the soaring heights of 1150 Lake Shore Drive to the opulent corridors of the Original Playboy Mansion, this tour invites you to delve into the heart of the city’s rich heritage. Discover hidden stories behind iconic facades, walk the paths of the influential, and immerse yourself in the elegance that has shaped Chicago. This isn’t just a tour; it’s your gateway to experiencing the soul of a city that prides itself on architectural marvels and legendary tales. Make history your playground and become the hero of your own Chicago adventure with us.

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Highlights

  • Experience Chicago's Architectural Wonders
  • Journey through History and Luxury
  • Discover the Secrets of Chicago's Elite

Included

  • Professional local tour guide

Route & Duration

Duration
Duration
2 hours
  • 1

    1150 Lake Shore Drive Building

    Iconic skyscraper offering breathtaking Lake Michigan views; a marvel of modern architecture.

    15 minutes
    Free Admission
  • 2

    John Wellborn Root House

    Historic residence of the famed architect; a glimpse into Chicago's architectural heritage.

    15 minutes
    Free Admission
  • 3

    Ambassador Chicago - JDV by Hyatt

    Elegant hotel embodying Chicago's rich history and sophistication; a stay worth experiencing.

    15 minutes
    Free Admission
  • 4

    N Astor St

    Prestigious street lined with architectural gems; a walk through Chicago's elite history.

    15 minutes
    Free Admission
  • 5

    Charnley-Persky House Museum

    Masterpiece showcasing the collaboration between Adler, Sullivan, and Wright; a cornerstone of architectural innovation.

    15 minutes
    Free Admission
  • 6

    McCormick Mansion

    Grandiose mansion reflecting Chicago's Gilded Age luxury; a journey into opulent past lifestyles.

    15 minutes
    Free Admission
  • 7

    Original Playboy Mansion

    Infamous landmark blending luxury with cultural history; explore the legacy of an entertainment empire.

    15 minutes
    Free Admission
  • 8

    E Elm St

    Picturesque street known for its stately homes and tranquil ambiance; a serene escape in the city.

    15 minutes
    Free Admission

Meeting Point

We will meet outside the 1150 Lake Shore Drive Building.

1150 Lake Shore Drive Building, 1150 N Lake Shore Dr, Chicago, IL 60611, United States See Map

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.