Walking Tours

Ronnie’s in-person guided walking tours are an amazing way to see the City of Chicago and learn about its incredible history.

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If you love architecture, Ronnie has a tour for you!

Ronnie is an architectural photographer and interior designer. Having studied architecture and historical homes/buildings for more than 30 years, he has a passion for historical preservation that shows in his tours. You’ll discover hidden gems and historical tidbits that bring you back in time.

Running throughout the year, Ronnie’s Doorways of Chicago guided walking tours offer a glimpse into the history of Chicago’s finest and most photographed neighborhoods, districts, and buildings. Lace up your walking shoes and book any of the tours below or gift them to a friend with a Walking Tour Gift Card. Either way, they’re an unforgettable Chicago experience.

Walking Tour Gift Cards

Give the incredible gift of amazing architecture with a Doorways of Chicago Tour Gift Card!  Gift Cards are available in any denomination and can be used on any upcoming walking tour. 

FAB Finds at the Fine Arts Building
INSIDE WALKING TOUR

Embark on a time travel journey to uncover Chicago’s best-kept secret: a 125-year-old architectural marvel.

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Step into the heart of Chicago’s enchanting artist’s colony with this exclusive tour inside the Fine Arts Building. Nestled in the vibrant cultural landscape of downtown Chicago, this architectural gem has stood as a testament to creativity and craftsmanship since its inception in 1898.

As you traverse the ornate corridors, walk up and down the grand staircase and ride some of the last manually operated elevators in the city, you’ll be transported back in time to an era when the arts flourished. The Fine Arts Building, originally built in 1893, housed the Studebaker Carriage Company’s showroom and factory.

This guided tour will unravel the stories embedded in the building’s exquisite architecture, highlighting its role in fostering creativity. Explore the studios that once hosted influential artists, musicians, and writers, immersing yourself in the same spaces that inspired the likes of Frank Lloyd Wright, Lorado Taft, and Sherwood Anderson.

Every corner of the Fine Arts Building whispers tales of the creative and enduring spirit of Chicago’s artistic heritage. Designed by Solon S. Beman, the architect behind the Pullman Palace Car Company, the building served as a hub for Chicago’s burgeoning arts scene in the late 19th century. Now, 125 years later, it continues to play the same pivotal role, preserving the old and perpetuating a new and exciting artistic colony within its historic walls.

TOUR SEASON:
This tour runs throughout the year.

STARTING POINT
Fine Arts Building
Suite 424
410 S Michigan Avenue

Chicago Art Deco Madness
WALKING TOUR

Discover the perfectly preserved Art Deco architecture of Chicago’s Loop, a testament to the Roaring 20s, on this engaging walking tour.

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Go on a captivating journey through Chicago’s Financial District and the N. Michigan Ave. Immerse yourself in the glamour of the Roaring 20s as we explore 7 stunning Art Deco buildings, each a masterpiece in its unique and individual way. Along the way, discover other notable properties and outdoor sculptures that contribute to the rich tapestry of Chicago’s architectural history.

As we stroll you will be transported back to the era of the New Machine Age, where Art Deco reigned supreme, celebrating the modern life of the time. Be prepared to be mesmerized by the intricate details and grandeur of these architectural gems. Ronnie will paint a vivid picture of life in the Roaring 20s, providing insights into the stories behind these iconic structures.

While some stops may include brief tours of lobbies, please note that on certain days, interiors may be closed. In those cases, Ronnie has curated a photographic tour that showcases interiors through his lens and historic photos from various preservation websites. This fun and fabulous walking tour promises an unforgettable experience, blending architecture, history, and the vibrant spirit of the Jazz Age.

TOUR SEASON:
This tour runs from May through mid-October.

STARTING POINT
231 S. La Salle St., in front of the Wintrust Bank Building

Historic Homes, Cottages, & Buildings of Wicker Park
WALKING TOUR

Uncover Wicker Park’s rich building and labor history as you explore mansions, cottages, and iconic structures in this vibrant neighborhood.

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Step back in time and uncover the hidden treasures of Wicker Park, a neighborhood that preserves the enchanting legacy of Victorian architecture and plays a crucial role in U.S. labor history. Join me on a walking tour through the cobblestone streets, where time seems to stand still, revealing a captivating potpourri of architectural wonders.

Wicker Park’s architectural diversity is a testament to its rich history, featuring styles such as Carpenter Gothic, Chateauesque, Italianate, Queen Anne, Romanesque, Second Empire, and eclectic designs that defy categorization. From lowly cottages to extravagant mansions, each structure whispers stories of a bygone era, reflecting a long-lost set of skills and an elegant suburban lifestyle that once flourished in Chicago.

As we admire the beveled, jeweled, leaded, and stained glass windows, along with the charming gazebos and gingerbread porches, we’ll also delve into the social fabric that shaped Wicker Park. Originally settled by a vibrant community of Germans and Scandinavians, both rich and poor, the neighborhood played a pivotal role in U.S. labor history.

This walking tour is a journey through time, where the architectural splendor and the echoes of labor history intertwine, offering a unique and immersive experience in the heart of Wicker Park.

TOUR SEASON:
This tour runs from late April through mid-November.

STARTING POINT
In front of the small workers’ cottage home at 1236 N. Hoyne Ave.

Craftsman BUngalows of Ravenswood Manor
WALKING TOUR

Explore the enchanting Arts & Crafts bungalows and cottages in Chicago’s Ravenswood Manor Historic District.

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Set out on a delightful journey through the Ravenswood Manor Historic District, a hidden gem nestled along the North Branch of the Chicago River. This tour explores the charm and enchantment of this captivating neighborhood, where Arts & Crafts bungalows, cottages, and homes tell tales of a bygone era.

As we meander through the picturesque streets, discover the architectural wonders that grace this historic district, each structure a testament to the city’s rich history and the visionary spirit of William E. Harmon, an innovative real estate pioneer. The Arts & Crafts style homes, with their distinctive features and intricate details will transport you back in time.

Learn about the stories behind these homes, the people who once lived within their walls, and the cultural significance that defines this charming enclave. Every house is a piece of history waiting to be discovered. This tour promises to unveil the charm and enchantment of this hidden gem, leaving you with a deeper appreciation for the rich tapestry of Chicago’s diverse neighborhoods.

TOUR SEASON:
This tour runs from May through mid October.

STARTING POINT
Ravenswood Manor Park
4640 North Manor Avenue

Retro River North
WALKING TOUR

Discover the history behind Chicago’s vintage and neon signs in the lively River North Historic District on this fascinating tour.

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Step into the enchanting world of Retro River North with my curated walking tour, where the stars of the show are the dazzling vintage signs and neon wonders that light up the night. You’ll experience a lovely evening stroll through the captivating River North Historical District, where every sign tells a story and every corner holds a piece of Chicago’s rich history.

As we meander through the streets, the tour showcases several establishments adorned with amazing vintage signs, each a testament to the charm of a bygone era. But this tour is more than just a visual feast of neon brilliance. You will also hear tales of many notable properties, ensuring that you not only see the signs but also understand the historical significance of the places they illuminate.

This is a fun and informative evening walk, where the magic of vintage signs meets the allure of River North’s historical treasures. Discover the stories behind the neon glow, and let each sign be a beacon inviting you to explore the vibrant history of this iconic district.

TOUR SEASON:
This tour runs from May through mid-October.

STARTING POINT
LaSalle Flower Shop 
731 N La Salle St

The Deep Pockets of Graceland Cemetery
WALKING TOUR

Come explore the opulent tombs and captivating histories of Graceland Cemetery’s wealthiest residents on our exclusive walking tour.

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Dive into this captivating journey through the hallowed grounds of Chicago’s Graceland Cemetery. As we stroll amidst the stunning and serene beauty of historic resting places, you’ll encounter the final resting spots of architectural visionaries like William LeBaron Jenney, John Root, Louis Sullivan, Mies Van der Rohe, and Daniel Burnham.

This unique walking tour not only unveils the grandeur of tombs and mausoleums but also shares the stories of Chicago’s celebrated architects, whose creativity shaped the city’s skyline. Join me as we pay homage to the masterminds behind iconic structures, exploring the eternal homes of those who left an indelible mark on the the city’s architectural landscape.

But our journey extends beyond the architects’ realm, as we also discover the final resting places of other notable figures with deep pockets—pioneers of industry such as Marshall Field, Palmer Potter, George Pullman, Walter Newberry, and more. Their legacies, intertwined with the fabric of Chicago’s history, add an extra layer of richness to this immersive tour.

Come along for an unforgettable experience, where history, architecture, and the eternal peace of these illustrious individuals converge in a captivating exploration of Chicago’s past.

TOUR SEASON:
This tour runs from late April through mid-November.

STARTING POINT
Graceland Cemetery
Administration Building
4001 N. Clark Street

Worker's Cottages of Oldtown Triangle
WALKING TOUR

Explore Chicago’s late 1800s Workers Cottages and more on this captivating architectural walking tour.

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Explore the resilient spirit of Chicago through a captivating walking tour that traces the city’s remarkable transformation from the ashes of the Great Chicago Fire in 1871. Join me on a journey through the streets where history and architecture converge, showcasing the enduring charm of the iconic workers’ cottages. These humble dwellings, once flourishing before and after the fire, now face the threat of urban development.

Discover the unique designs and construction styles of these delightful cottages, each telling a story of Chicago’s architectural evolution. As demand for higher-density housing grows, the very essence of these historic homes is at risk. The tour will unveil not only individual cottages but also rare instances of entire blocks adorned with these charming structures.

Immerse yourself in the rich tapestry of Chicago’s past as we delve into fascinating tales dating back 150 years and beyond. From the resilience born out of adversity to the architectural gems lining the streets, this walking tour promises a unique blend of history, design, and the captivating spirit of the Windy City.

TOUR SEASON:
This tour runs from April through mid November.

STARTING POINT
Meet in front of the rowhouse at 164 W. Eugenie St

A MAGICAL WALK THROUGH TIME

"Absolutely magical walk through time to discover the amazing worker’s cottages of Chicago. Passionate tour guide Ronnie leads a walk through the history of these wonderful homes in a charming neighborhood you have to see to believe. Ronnie’s enthusiasm and knowledge are endless and his engaging narrative will enchant your experience of discovering these delightful cottages, the neighborhood, and lots of surprises along the way. I highly recommend this tour for any resident or visitor to Chicago!!!"
TripAdvisor.com User

Discover hidden gems

"We moved to Chicago eight months ago and Ronnie’s tour was a perfect mix of history, architecture, culture and neighborhood to start to get us acquainted with the beauty of our beautiful new city. Chicago is a city of neighborhoods, and of a million hidden gems. On this tour, you really get to see a few of them most major “best of Chicago” tours would never uncover. Highly recommend! "
TripAdvisor.com User

WONDERFUL TOUR!

"Very enjoyable and informative tour! I especially appreciated how Ronnie pointed out so many specific architectural features on the building facades. I learned a lot of new words and I'll really enjoy when I see them around Chicago and can name them myself!"
TripAdvisor.com User

AMAZING TOUR!

"Amazing tour! Ronnie’s passion for architecture comes through with not only the traditional tour details you’d expect, but personal anecdotes and humorous tidbits that you’re not going to find on mainstream tours that make the tour so memorable. Highly, highly recommended."
TripAdvisor.com User

INFORMATIVE AND ENTERTAINING

"If you are interested in the history of Chicago and it's architecture I highly recommend taking a Tour with Doorways of Chicago. Ronnie is knowledgeable, friendly and loves to share. I loved learning new facts about places I have walked by for years. Such a delightful way to spend an afternoon."
TripAdvisor.com User

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