Chicago Magnificent Mile

Tour Creator

Wendy Bright is passionate about sharing the beauty and wonder that is Chicago. She has an MA in Art History with an emphasis on architecture. For over 25 years she…Read More Bio »



Remote Tour Included



Our tour will show you the highlights of this famous Chicago street. We will learn about some of the Chicago’s most iconic skyscrapers, exotic and elegant private clubs, and historic hotels. We will look at architecture old and new and explore how North Michigan Avenue has evolved over time.

Chicago was long known for being a sprawling, industrial powerhouse, gritty, dirty, and not a little corrupt. With the success of the gleaming White City at the heart of the 1893 Chicago World’s Fair, the city’s leaders were inspired to clean up and transform the less than beautiful parts of the permanent city. The resulting 1909 Plan of Chicago called for a remaking of the city into an elegant “Paris on the Prairie.” This shopping boulevard was part of the plan.

We will give you the grand sweep of history along the Magnificent Mile, including highlights of Chicago’s early history. You will come away with a deeper appreciation of this iconic street and a more thorough understanding of Chicago.

Avoid the Crowds

Allows you to explore without having to be shoulder-to-shoulder in a large tour group

Expert-created Tour

Written by a long-time Chicago tour guide with a Master of Arts

GPS Directions

Easy-to-follow GPS directions to get you from one point to the next on your tour

Highlights include:

Wrigley Building, Historic Water Tower, and First Presbyterian Church

Remote Tour Included

As with all our tours, a remote tour is included that can be enjoyed from home


Chicago: Magnificent Mile

  1. Plaza in front of Wrigley Building - We will explore the backstory of Chicago’s Magnificent Mile and the reminders of the city’s earliest history.
  2. Wrigley Building - We will explore the beloved and iconic Wrigley Building’s design and history.
  3. Tribune Tower - We will learn the remarkable story of this world-famous building.
  4. Medinah Athletic Building (Interior) - We will discover the original interior of this exotic private men’s athletic club, why it was designed as it was, and how it is a hotel today.
  5. McGraw-Hill Building - We will continue the story of this street from 1920 to today and learn why it was called the Magnificent Mile, then explore a fascinating account of architectural preservation.
  6. Chicago Women’s Athletic Club - We will discover the story of the world’s first women’s athletic club and their building.
  7. Former Crate & Barrel flagship store, and Starbucks Reserve Roastery - We will discuss an excellent example of adaptive reuse in this former Crate & Barrel flagship store, today’s Starbucks Reserve Roastery.
  8. Historic Water Tower, Great Chicago Fire - In the middle of this buzzing retail district is a poignant reminder of the tragedy of the Great Chicago Fire and of the city’s recovery, the Historic Water Tower.
  9. John Hancock Tower - The city of skyscrapers has some beloved favorites and the John Hancock is one of them. We will learn the story of this groundbreaking supertall building and how you can visit its heights.
  10. Fourth Presbyterian Church (Interior) - This century-old church was here before the street was developed as an exclusive shopping enclave and it provides a peaceful respite. We will explore Fourth Presbyterian’s almost entirely original interior.

Check out a free sample of this tour!

Share this tour


Get the tour in our app today!