Please enable cookies in your browser to place a booking

how do I enable cookies?

10/20/18 — 10/22/18 10/20/18 — 10/24/18 10/20/18 — 10/26/18 or
Sat 20 Oct Sun 21 Oct Mon 22 Oct Tue 23 Oct Wed 24 Oct Thu 25 Oct Fri 26 Oct
Loop Interior Architecture Walking Tour Book Now Available Book Now Available Book Now Available Book Now Available Book Now Available Book Now Available Book Now Available
Loop Interior Architecture Walking Tour

Loop Interior Architecture Walking Tour

Explore Chicago from an insider's perspective with architectural interiors and some of the underground passages of the Pedway.

Interior Architecture Tour Overview

With so many architecture tours to choose from, how do you know your guide isn’t going to be a volunteer tour docent rambling a bunch of dates, names and minutia? Come on a tour with Chicago Detours!

On the Loop Interior Architecture Walking Tour, you’ll step inside magnificent lobbies, corridors, and the underground Pedway system for an in-depth, personal approach to a Chicago architecture walking tour downtown. The Loop Interior Architecture Walking Tour takes you on a creative route that weaves through buildings and secret short-cuts. 95% of the tour takes place inside, making it great for any kind of our Chicago weather.

Tour guests share iPads with archival images of maps, historic photos and documentary video clips while the tour guide shares stories of Chicago history. As one of the top-rated tours of Chicago, the Loop Interior Architecture Walking Tour has received plenty of five-star ratings on Yelp.

Our fun and passionate tour guides are highly trained professionals with degrees in architecture, design, art history and history. They know how to connect with a group, spark imaginations, and communicate new concepts in relating to architecture.

Looking at the outside of buildings, such as with architectural boat tours, can be a great first step in engaging with Chicago architecture. For the next level of connection with Chicago architecture, go inside of the buildings. You will appreciate Chicago architecture from new perspectives. From the interiors, you can truly experience architectural space rather than from the more isolated perspective of a downtown sidewalk.

If you are looking for a Pedway-only tour, this walking tour is much more than just a Pedway walking tour. We  venture into beautiful lobbies and corridors of both Chicago landmarks and lesser-known historic sites.

To be honest, walking through parts of the Pedway is like walking through a modern basement. It is generally not very visually enticing. A portion of this tour takes you into Pedway passages, and you get the gift of our color-printed map of the Chicago Pedway System so that you can explore on your own.

This Chicago architecture walking tour is also available as a private group tour for nine or more guests.

Interior Walking Tour Highlights

  • Church in a skyscraper with stained glass windows
  • The “Chicago Picasso” sculpture
  • Chicago’s underground Pedway system
  • The contemporary Block 37 development
  • Marshall Field’s department store
  • Sparkling Tiffany mosaics
  • Chicago Cultural Center

Stories and Ideas

  • How to read Chicago architecture to understand history
  • Stories of corruption and generosity
  • Why the ‘L’ is elevated
  • Design psychology behind interior space
  • A surprising history of shopping
  • Religion and social diversity

Interior Architecture Tour Includes:

  • Engaging tour guide commentary
  • Shared use of iPads with video & photos
  • Professionally printed Chicago Pedway map
  • Special Chicago gifts
  • Discounted flat-rate parking at Grant Park North Garage ($15)
Walking distance: 0.5 mile

  • Duration : 2 Hours (approx.)
From USD $26.00

Enter Number of Participants *

Choose a Time *

Historic Chicago Walking Bar Tour Book Now Available Book Now Available Book Now Available × × Book Now Available Book Now Available
Historic Chicago Walking Bar Tour

Historic Chicago Walking Bar Tour

Eat, drink and learn about Chicago's entertainment history with appetizers, beer or wine, and beautiful historic architecture.

Historic Chicago Pub Crawl Tour Overview

Join us for a historic Chicago pub crawl with an educational twist! You’ll explore Chicago’s entertainment history and learn about prohibition, jazz, theater, vices, and social clubs. In addition to the tour guide’s stories, guests interact with historic photos and videos on shared iPads to connect with Chicago’s party past.

Our evening walking tour stays mostly indoors, making it great for any kind of weather. We’ll enjoy our appetizers and your choice of wine or beer at three drink stops and explore history and architecture in between. In addition to bar stops, our groups see magnificent lobbies, Gilded Age mansions, and Chicago’s multiple underground layers. Drinks are on you - please see below. 

Who comes on a historic pub crawl tour of Chicago? Many tour guests enjoy the tour’s fun and social dynamic. Solo travelers often join us. As a great Chicago date idea, it can be a fun thing to do in Chicago with your boyfriend or girlfriend. Groups of friends make the tour into a cool weekend event, too. Family groups love it!

This tour more than a historic Chicago pub crawl – you’ll eat, drink, and learn about architecture, Prohibition-era history, and party culture.

We’d like to say it’s a Speakeasy Tour or a Chicago Prohibition Tour, but truthfully very few bars in Chicago remaining today were ever speakeasies. We did find one stop on our tour that was a true speakeasy though, and an early Chicago jazz club to boot!

Who wants to listen to a volunteer tour docent rambling dates and names? Don’t fret with us – our tour guides are highly trained, smart and fun! We are proud to be a top-rated Chicago tour company, with five-star ratings on Yelp and TripAdvisor.

The Historic Chicago Bar Walking Tour is like a mix of a food tour, an architecture walking tour, and a mobile documentary film. Book your tour early as the historic Chicago pub crawl often sells out. It’s a unique Chicago thing to do this summer!

Walking Bar Tour Highlights

  • Michigan Ave, aka “Magnificent Mile”
  • Tribune Tower
  • Chicago’s underground layers
  • The famous Billy Goat Tavern
  • A former historic jazz club and speakeasy
  • A 19th-century mansion

Stories and Ideas

  • Architecture as a cultural artifact
  • The “Hex of the Billy Goat”
  • Chicago jazz era
  • History of Chicago breweries
  • Prohibition and gangsters
  • 1960’s swanky nightlife
  • Private clubs and debauchery

Historic Chicago Pub Crawl Prices

Reservations are $36 per person. Guests bring cash for beverages. Total cost is $39-$58 per tour guest inclusive of tour, food, beer, wine, gratuities, taxes. 

Chicago Walking Bar Tour Includes:

  • Engaging tour guide commentary
  • Shared use of iPads with historic photos and video clips
  • Appetizers
  • Special gifts
  • Discounted flat-rate $15 parking at the Grant Park North Garage (ask for voucher at tour)

Tour Reservations Do Not Include:

Drinks and server gratuities. All guests must choose a beverage for the walking tour and bring cash to cover 2.5 servings of beer ($23), wine ($29), soda ($8) or water ($3).

Walking distance: .75 miles

  • Duration : 150 Minutes (approx.)
From USD $36.00

Enter Number of Participants *

Choose a Time *

1893 World's Fair Tour with Bars Book Now Available × × × Book Now Available × Book Now Available
1893 World's Fair Tour with Bars

1893 World's Fair Tour with Bars

A combination of drinks with incredible architecture, fascinating historical stories of turn-of-the-century Chicago, and visual scavenger hunts.

1893 World’s Fair Tour Overview

This very special walking tour digs into how and why the 1893 World’s Fair captures imaginations more than any other event in Chicago history. Unlike other World’s Fair tours and Devil in the White City tours, which likely revolve around facts and trivia, you’ll dig deeper on this tour.

On this fun and insightful walking tour, you’ll venture into beautiful architectural spaces from the era. You will play a few thoughtfully designed games, like visual scavenger hunts. Along with guide commentary, your guide will show you on shared iPads material from archives and photographs that illuminate this event, also known as the 1893 World’s Columbian Exposition.

This downtown tour visits some of the few remaining and spectacular buildings from the time of the World’s Fair. The fairgrounds themselves were south of downtown, but you can best see the impact of the fair in the Loop. Here the architecture and landscape still show the World’s Fair imprint even today, nearly 125 years later. And beyond just looking at buildings from outside, our mostly indoor walking tour sees the beauty of architectural details within.

On this walking tour, you will eat a couple light snacks (we used to call this a “food tour” but have minimized the food, just fyi in case you’re reading reviews on Yelp or TripAdvisor). Plus, you can opt to get drinks (on you), too!

You can think of this 3-hour-long walking tour as being 5% outdoors, 95% indoors, 20% clue-based games and visual scavenger hunts, 10% drinking time, and 100% awesome historical tour time. We know the math doesn’t add up – we hope you get the idea!

With just intermittent walks outside, the 1893 World’s Fair Tour makes for a great walking tour in all seasons. This tour makes the World’s Fair’s lasting impact come to life. We hope you’ll join us!

Walking Tour Highlights
  • Colorful mosaics in a hotel built for the 1893 World’s Fair
  • The sweeping grand lobby of the Auditorium Building
  • Ride one of the downtown’s last human-operated elevators
  • A secret building hidden in an alley
  • See the Monadnock Building, a landmark early skyscraper
  • The opulent Chicago Athletic Association Hotel, once an exclusive men’s club

Stories and Ideas

  • The rapid changes in culture around the turn of the century
  • The 1893 Fair’s array of foods and even food sculpture
  • Parlor songs of the past
  • The beginnings of consumer culture and advertising
  • Amusements on the Midway at the 1893 World’s Fair

1893 World’s Fair Tour Includes:

  • Professional tour guide commentary
  • Shared iPads with historic photos
  • Light snacks
  • Game prizes and gifts

Reservation Does Not Include:

  • Drinks: At the tour meeting spot, we welcome you to get a drink at the bar before check-in. To streamline the tour, we take your order and cash for your second drink at check-in ($6 for beer, $8 for wine, includes gratuity). At the third drink stop, you may independently purchase a beer, wine, or cocktail of your choice.
  • Dietary restrictions: two small snacks are included. We may be able to accommodate vegetarians. If you are gluten-free, dairy-free, or have other allergies, we cannot make substitutions.
  • Tour guide gratuity.
Walking distance: 0.9 mile

  • Duration : 3 Hours (approx.)
From USD $40.00

Enter Number of Participants *

Choose a Time *

Best Architecture Walking Tour for Design Lovers $22.00
× × × × × ×
Best Architecture Walking Tour for Design Lovers

Best Architecture Walking Tour for Design Lovers

This fun and creative Chicago architecture walking tour puts architecture in context of the arts and pop culture.

Best Architecture Walking Tour Overview

What does Michael Jackson’s Thriller have to do with the design of a post-modern skyscraper? Or Andy Warhol’s soup cans with modernism? The Architecture Walking Tour for Design Lovers is a creative tour of Chicago architecture. We designed it for curious people.

On this condensed architecture tour of an hour and a half, you will learn about architectural styles through their connections with technology and culture. All arts are a reflection of an age. Styles in creations like architecture, graphic design, fashion design and pop culture have similar qualities when they come from the same era. We will compare architecture with contemporaneous works other media to help us learn how to identify architectural styles.

This includes pop culture, like shoulder pads fashion of the eighties and comic books! We’ll look at lots of eye candy while expanding our understanding of architectural styles and Chicago history. It’s a very visual and interactive tour.

Most of all, we’ll understand architectural style’s deeper connections with history. And we’ll consider how the advancements in technology and engineering have shaped buildings. This is the foundation of a Chicago architecture tour.

The fun and creative educational approach of this Chicago architecture walking tour makes it unlike any other architecture tour in the city.  You won’t be bogged down with dates and names with us, but we will introduce you to new ideas on how to look at architecture.

And the tour is “the best” for Detours-minded folks. This best architectural walking tour appeals to both Chicago locals and visitors. People well-versed in art history will enjoy it, as well as tour guests new to looking at art and architecture. You will learn about various architectural styles, both by looking at buildings in front of us and at images and video on shared iPads.

Have you been on the architectural boat tour, perhaps with the Chicago Architecture Foundation? This would be your next step for the curious who want a deeper understanding of Chicago architecture.

Our architecture walking tour goes south of the Michigan Avenue bridge. This is a route where many people walk but rarely look up. We conclude at the very new contemporary playground of Maggie Daley Park.

With so many architecture tours to choose from, how do you know you aren’t going to get a volunteer tour docent rambling dates, names and minutia? Come on a tour with Chicago Detours and our fun, passionate, and highly trained tour guides. We have a solid five stars on Yelp andTripAdvisor.

Architecture Walking Tour Highlights

  • Chicago’s underground layers
  • Michigan Avenue Bridge
  • The gold-topped Carbide and Carbon Building
  • The massive Mies van der Rohe’s Illinois Center
  • The Diamond Building and its anatomical nickname
  • Jeanne Gang’s famous Aqua Tower
  • The new Maggie Daley Park

Architecture Walking Tour Stories and Ideas

  • Fort Dearborn and the “simple life”
  • Chicago School of Architecture
  • Art Deco and the Roaring ’20s
  • Mechanization and the spirit of modernist architecture
  • The fun shapes of post-modern forms
  • The latest trends in city evolution and living

Walking Tour Tickets Include

  • Shared iPads with historic photos and video clips
  • Engaging tour guide commentary
  • Special gifts
  • Discounted flat-rate parking at Grant Park North Garage ($15)
Walking distance: 0.5 mile

  • Duration : 90 Minutes (approx.)
From USD $22.00

Enter Number of Participants *

Choose a Time *

Factories to Calories Fulton Market Food Tour Book Now Available × × × × × ×
Factories to Calories Fulton Market Food Tour

Factories to Calories Fulton Market Food Tour

Discover the history and dramatic transformations of this industrial-to-chic neighborhood while sampling delicious gourmet foods.

Discover the dramatic transformations of Chicago’s most rapidly booming neighborhood on this walking tour. Over the course of this two-hour excursion, you’ll get a glimpse of Fulton Market’s meatpacking past and enjoy a taste of its gourmand present.

We call our Fulton Market food tour the “Factories to Calories” tour because of the area’s shift from a place of production of appliances, furniture and meat products to a hub of consumption of food and drink. The walking tour starts with a grand view. You’ll see the train and highway systems that made Fulton Market into a vital industrial and meatpacking district. From there, we’re off on a one-mile jaunt through a neighborhood defined by change.

Guests will sample some of the culinary delights of Fulton Market without feeling overstuffed. You’ll get to taste artisanal deli meats from Publican Quality Meats and half of the signature sub at J.P. Graziano, a family-owned shop in its third generation. The tour finishes with pickles and a craft beer sample at Haymarket Pub & Brewery. Please keep in mind that this is an educational tour. Other food tours may focus more on eating, but we will eat a light amount and most of all learn!

Until very recently, Fulton Market was a gritty meatpacking district. You’ll see the historic Fulton Market buildings that housed 19th-century meat and produce vendors. Today, of course, they’re home to an array of high-end restaurants. We’ll discuss how even the streets and sidewalks themselves were designed to aid the often grisly work of butchering and processing meat.

Beyond that, this walking tour of Fulton Market will explore just how quickly the neighborhood has changed and gentrified. As recently as the ’80s and ’90s, Fulton Market was home to underground parties, drug busts and low-rent art galleries. Today you will find high-end retailers and headquarters for corporations like Google and McDonald’s.

And how did this all happen?! Your tour guide will talk about how the city of Chicago eased the way for gentrification over the past 20 years. As we walk through the neighborhood, we will see active demolition and construction. Finally, we’ll discuss the infamous Haymarket Affair and labor history with drinks and snacks at the eponymous brewpub.

Tour is capped at 14 tour guests. Space is very limited and tours do sell out, so we recommend booking your Fulton Market food tour ASAP!

This Fulton Market food tour is also available as a private group tour for nine or more guests.

Fulton Market Tour Highlights

  • A grand view of the railroad tracks and surrounding industrial buildings
  • Redeveloped meatpacking facilities, now trendy restaurants
  • A giant cold storage facility, now Google offices
  • “Gourmet Food Trend Row”
  • The striking art deco Richter Foods building
  • Hidden clues in the landscape tied to the meatpacking past

Walking Tour Stories and Ideas

  • Chicago’s meatpacking history and the role of Fulton Market
  • Impact of transportation infrastructure on neighborhood identity
  • The industrial neighborhood disappearing before our eyes
  • Family businesses and traditions
  • Urban renewal and redevelopment
  • Labor history and the Haymarket Affair

$42 Walking Tour Includes

  • Engaging tour guide commentary
  • Artisanal deli meat sample from Publican Quality Meats
  • Beverage and half-size signature sub at J.P. Graziano
  • Sample-size glass of beer and pickles at Haymarket Pub & Brewery
  • All gratuities for servers
  • Special gifts

Tour Location

We start inside Stumptown Coffee Roasters at 311 N Morgan St. Parking recommendation will be included in your confirmation email.

We end inside the Haymarket Pub & Brewery at 737 W. Randolph St.

  • Duration : 2 Hours (approx.)
From USD $42.00

Enter Number of Participants *

Choose a Time *

Old Polonia and Wicker Park Walking Tour with Food × × × × × × ×
Old Polonia and Wicker Park Walking Tour with Food

Old Polonia and Wicker Park Walking Tour with Food

We will explore the past and present of the people, architecture, and foods of these vibrant and changing neighborhoods of Noble Square and Wicker Park.

Wicker Park Walking Tour Overview

On this Wicker Park walking tour, we will explore the past and present of the people, architecture, and foods of two vibrant and changing neighborhoods. In addition to Wicker Park, we tour Noble Square. This Chicago neighborhood was once known as “Old Polonia” and is located within the West Town neighborhood.

Wicker Park has been studied by sociologists around the world for its rapid transformation in the ’80s and ’90s. Wicker Park had been home to gang bangers, drug addicts and prostitutes. Instead today it is often ranked in lists of “Coolest Neighborhoods” in America. Now neighboring Ukrainian Village and Noble Square have been moving in the same direction, too.

The Chicago Detours kind of food tour means that beyond just eating, we are going to really learn. To have a more meaningful connection with the places we visit, stories on this walking tour range from the voyage of Polish immigrants to the “bard of the down-and-outer” of Nelson Algren, to the “Die Yuppie Scum” graffiti of the ’90s gentrification movement.

Our walking tour starts at the former “Polish Broadway” with a visit inside a stunning Polish Catholic Church, filled with paintings, gold leaf details, and sweeping arches. Our walk around the Old Polonia neighborhood reveals clues to incredible contrasts of old and new, like a taqueria in a building from a 1930s hamburger joint or one of Chicago’s last newspaper stands. Over a huitlacoche quesadilla with home-made tortillas, we consider Mexican immigration to Chicago and Ashland Avenue’s “taco row.” Then we sample home-style Polish food in a restaurant that feels just like going to visit your Polish grandmother.

We take the CTA up to the Damen stop to stroll through the blooming park of Wicker Park (guests bring their own train cards). In this vibrant park we begin to see the neighborhood mix of people, before wandering down “Beer Baron Row” to see massive 19th century mansions. For this Wicker Park walking tour, you’ll hear the history of the Turkish Baths, which often peeks interest from Blue Line riders that see it from the CTA train. We’ll consume the new school vibe of the hip neighborhood with a gourmet doughnut from Stan’s Donuts. And our tour concludes by the massive gears of a bank vault, now a Walgreen’s Pharmacy.


Wicker Park Walking Tour Highlights

  • Step inside a dazzling Catholic Church
  • Walk by Gilded Age mansions on “Beer Baron Row”
  • Eat Polish food like grandma used to make
  • See writer Nelson Algren’s home
  • Step inside a bank vault, now a pharmacy

Stories and Ideas

  • Old Polonia, aka “Polish Downtown”
  • What old Wicker Park was like
  • Mexican immigration to Chicago
  • The ’90s gentrification of Wicker Park
  • Current changes in Chicago neighborhoods

Wicker Park Walking Tour Includes

  • Expert guide commentary
  • Special Gifts
  • Tastings at top-rated establishments:
    • La Pasadita
    • Podhalanka
    • Stan’s Donuts

 Tickets Do Not Include

CTA train fare – you must bring your own Ventra card for one train ride with the tour group.

  • Duration : 150 Minutes (approx.)
From USD $45.00

Enter Number of Participants *

Choose a Time *

Español - Tour de Arquitectura del Loop × × × × × × ×
Español - Tour de Arquitectura del Loop

Español - Tour de Arquitectura del Loop

En este tour arquitectónico a pie, entrarás en hermosos vestíbulos, corredores, y el sistema Pedway subterráneo para experimentar un método exhaustivo y personal al tour del centro de Chicago.


Pasa adentro para experimentar otra clase de tour de arquitectura. 

Chicago tiene muchos tours de arquitectura para escoger. ¿Cómo  se sabe si el guía turístico no es un voluntario que no hace más que repetir nombres y fechas? ¡Ven con nosotros al tour a pie de arquitectura interior con Chicago Detours!

En este tour, visitarás magníficos espacios interiores y la vía peatonal subterránea, que en Chicago se llama “El Pedway.” Hemos planificado una ruta creativa que entreteja edificios y pasajes secretos. Tendrás una sólida perspectiva de la historia de Chicago, y una nueva perspectiva al mirar nuestra famosa arquitectura desde afuera y desde adentro! El 95% del tour se desarrolla desde el interior, lo cual es perfecto para cualquier tipo de clima.

El guía turístico compartirá cuentos sobre la historia de Chicago mientras que los invitados compartan sus iPads repletas de mapas y fotos históricas, y videos documentales. Aspectos interesantes incluyen una iglesia dentro de un rascacielos, una urbanización contemporánea, y una tienda por departamentos histórica con mosaicos radiantes de Tiffany.

El Tour a Pie de Arquitectura Interior del Loop es uno de los tours más valorados en Chicago. Ha recibido cientos de calificaciones de 5 estrellas en Yelp y TripAdvisor. Nuestros guías turísticos son profesionales altamente entrenados y con formación en historia, humanidades y arquitectura. Ellos saben conectarse con el grupo y despertar la imaginación.

Los tours externos, como las salidas en bote, solo te permiten ver la parte externa de los edificios. Y puede ser un buen primer paso, pero tienes que entrar para experimentar por completo la arquitectura de Chicago. Ir más allá de la fachada significa experimentar realmente la dinámica psicológica de la arquitectura del espacio.

Nos aventuramos a vestíbulos y corredores hermosos tanto en los lugares de estado histórico de Chicago como en los sitios históricos menos conocidos. Honestamente, ciertas partes del systema subterránea del Pedway parecen un simple sótano, no son muy estimulantes visualmente. Una porción del tour nos lleva al Pedway, y recibirás como regalo un mapa del Pedway imprimido a color. ¡De esta manera puedes explorar todo el sistema por tu cuenta!

Este tour es una excelente introducción para los visitantes de Chicago, mientras que los lugareños obtienen una perspectiva completamente renovada al mirar la arquitectura y los detalles que nunca habían notado en el centro de Chicago. 

Este tour a pie de la arquitectura de Chicago también está disponible para grupos privados de nueve o más.


  • Iglesia en un rascacielos con ventanas de vitral
  • Escultura “Chicago Picasso”
  • Sistema Pedway subterráneo de Chicago
  • La urbanización contemporánea Block 37
  • La tienda por departamentos, antes el viejo Marshall Field’s
  • Mosaicos brillantes de Tiffany
  • Centro Cultural de Chicago


  • Cómo leer la arquitectura de Chicago y comprender su historia
  • Historias de corrupción y generosidad
  • ¿Por qué es elevado el “L”?
  • Psicologia del diseño del espacio interior
  • La sorprendente historia de las compras
  • Religión y diversidad social


  • Comentario cautivador del guía turístico profesional
  • Uso compartido de iPads con videos y fotos
  • Mapa del Pedway profesionalmente imprimida
  • Regalos especiales de Chicago
  • Descuento de tarifa plana en el parqueadero del Grant Park North Garage ($15)

  • Duration : 2 Hours (approx.)
From USD $26.00

Enter Number of Participants *

Choose a Time *

Free Chicago Walking Tour Inside a Historic Skyscraper × × × × × × ×
Free Chicago Walking Tour Inside a Historic Skyscraper

Free Chicago Walking Tour Inside a Historic Skyscraper

This free walking tour of the Monadnock Building showcases its monumental architecture, gorgeous interiors and fascinating history.

This free Chicago walking tour of the Monadnock Building showcases its monumental architecture, gorgeous interiors and fascinating history. The groundbreaking restoration of this 19th-century skyscraper demonstrates the value of preserving historic architecture. Gratuities for this brief and mostly indoor tour, which is available for a limited time, will benefit Preservation Chicago!  


On this free Chicago walking tour, you’ll discover the elegant architecture of the Monadnock Building, one of the oldest skyscrapers of downtown Chicago. During your 30-minute-long architectural walking tour, your professional tour guide will share the larger-than-life story and structure of this classic 1890s skyscraper. You’ll enter the building to experience the Monadnock’s inspiring interiors. The tour will be inside 75% of the time, meaning you’ll be comfortable on this tour even in inclement weather.

The tour group starts in a cafe, and then steps outside to contrast the dark brick of the Monadnock Building with the gleaming terracotta of the neighboring historic Fisher Building. Once inside the Monadnock, it’s like stepping back to 19th-century Chicago. Tour guests see architectural details like intricate brass doorknobs, glamorous aluminum stairs and old-fashioned mailboxes. You’ll also see old-time businesses like a haberdashery and florist. The original look and feel of the Monadnock was carefully restored in the 1980s. Thanks to the foresight of the building’s current owner, today our walking tour groups can enjoy the enchanting details and extravagant materials of commercial architecture from a century ago. 

After we explore the Monadnock’s beautifully restored interiors, we step outside briefly. Here our free walking tour concludes by connecting the Monadnock’s monumental exterior with Mies Van Der Rohe’s modernist style across the street.

The Monadnock Building demonstrates how crucial it is to preserve Chicago’s incredible architecture. Chicago Detours is committed to supporting efforts to save our city’s historic architecture. Thus our tour guides are donating 100% of all gratuities received on this free walking tour to Preservation Chicago. This non-profit organization “protects and revitalizes Chicago’s irreplaceable architecture, neighborhoods and urban spaces.”

Please note that because we are walking and standing on the tour we have to call this a “walking tour” but we are not walking much distance at all.

This tour is free and offered weekly on Fridays until December 8th. Reservations are required! Please book now.


As a top-rated tour company, with professional (not volunteer) tour guides, why are we offering this Chicago walking tour by foot for free?

  • To give back to the community! Tour guides will donate all gratuities to Preservation Chicago.
  • To welcome new walking tour guests! Come experience our style of walking tour.
  • To thank our previous tour guests and see them again!
  • Lastly, the Monadnock Building is our office home. We love sharing our appreciation for the Monadnock Building’s incredible architecture on this free walking tour. 

LENGTH - .5 hour
DISTANCE - .2 mile
COST - FREE - all gratuities donated to Preservation Chicago

Fridays, 12:30pm

- Architecture by Chicago masters Burnham & Root and Holabird & Roche
- Historic details like old-fashioned mailboxes, original doorknobs and ornate light fixtures
- Dramatic cast-aluminum staircases
- Original 19th-century mosaic tile floor preserved beside a modern replica
- Old-timey businesses like a haberdashery, shoe repair shop and florist

- Chicago’s rapid growth at the end of the century
- The preservation and restoration of historic architecture
- Connections between the Chicago School of architecture and Modernism
- Challenges of precise engineering in the nineteenth century

- Professional tour guide commentary
- Discount for our other walking tours

Tour meets inside Dollop Coffee at 343 S. Dearborn. Look for the tour guide with the name tag and clipboard.
Tour ends inside the Monadnock at 53 W Jackson

  • Duration : 30 Minutes (approx.)
From USD $0.00

Enter Number of Participants *

Choose a Time *