A New View of Chicago from the Inside and Out

by J. Michael Albert, a local Chicago historian and community organizer

Chicago has countless opportunities for exploration available to tourists and natives alike, from well-known spots on well-worn paths to hidden wonders and off-the-beaten-path treasures. From river tours, to trolley rides, to guided bike, segway, walking tours and more, your choices are nearly endless -- and often difficult to narrow down. Even after reading reviews, choosing from among the many options proves to be a daunting task.

As a Chicago historian and entertainment journalist, it’s my job to find the gems. Recently I had the opportunity to be a guest on several sneak-preview tours, each showcasing a different route, with one of the city’s newest offerings, Inside Chicago Walking Tours, with Hillary as my guide – a seasoned Chicago tour guide and linguist with a knowledge bank of Chicago architecture and history that rivals that of any historian. It made sense when I later learned that Hillary also has over ten years of improvisational comedy training and performance experience, as well as a background in teaching, research, and tour development, as the tour turned out to be the most entertaining, educational, and well-rounded one that I’ve had the pleasure to experience.

Part of Hillary’s inspiration for founding her own touring company came after developing new tours for a major boat tour company in Chicago.  She decided to create her own company based on her standards, vision, and passion for architecture, sharing her knowledge and love for the city that she calls home -- characteristics that you quickly appreciate when you meet her.

Hillary’s approachable and down-to-earth nature put me at ease right away, and I could tell this wasn’t going to be the average tourist venture but something more special and engaging. She begins by putting the wonders of Chicago’s renowned architecture into perspective, noting the sheer magnitude of work and number of individuals that go into erecting the skyscrapers, buildings, and monuments we take for granted each day, and explaining that each has an original story to tell – many of which Hillary reveals over the course of the tour in her characteristically engaging narrative style. The tour balanced both architectural facts and a real understanding of the differing styles and their eras with historical information as well as folklore and interesting anecdotes – setting itself apart from many guided cruises or treks around the city that end up being a overwhelming (and forgettable) list of facts that I may as well have Googled. Instead, Hillary makes each tour both a fun adventure and a learning experience with her storytelling approach, communicating many historical facts, and adding dashes of humor and candid moments, and you carry home with you the memories of an organic, unscripted, unique tour experience.

Perhaps what sets Inside Chicago Walking Tours apart from other tours the most is the element that lives up to its name: not only are you seeing the historic buildings up front and personal from the outside, but you are often guided through the inside of many of them, giving you an intimate perspective on not only the facades and exterior structures, but also the inner details and design, and indeed the history of these marvels of construction. It’s all articulately narrated by one of the most qualified guides I’ve had the pleasure of meeting. And by the nature of being a walking tour, it provides visitors with a truly multisensory experience of Chicago as they voyage through downtown and hear the roar of the L, feel the buzz of activity, and delight in all the other enchanting stimuli that you simply can’t experience from a boat or bus.

Inside Chicago Walking Tours embodies the spirit of the touring adventure by displaying Chicago’s uniqueness through a mixture of architecture, astonishing facts, and incredible history, with dashes of "insider" Chicago folklore, tales, and traditions that no other tour company can give you. Each of the tour routes covers a combination of both the time-honored and the esoteric, and the Inside Chicago Walking Tours website describes each at length so that you can be the judge as to which adventure you embark upon.

Hillary’s tour left me feeling like I had just gone on an inspiring expedition that gave me a newfound perspective and respect towards the city I write about and call home, along with an enlightened take on its many architectural masterpieces. Whether you’re visiting for the first time or have called Chicago home for decades, you can now take a compelling -- and affordable! -- walk through the city, seeing it inside and out, a walk that encompasses so much more than the average guided sightseeing excursions around the city.  Inside Chicago Walking Tours guides visitors on a delightful journey to Chicago's rich past, through its evolving present, and into its fascinating future.  It reminds me of the many, many reasons I love this city.