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9/21/19 — 9/23/19 9/21/19 — 9/25/19 9/21/19 — 9/27/19 or
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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: 0.7 mile

  • Duration : 2 Hours (approx.)
From USD $28.00

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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), or water ($3).

Walking distance: .75 miles

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

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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

On this fun and insightful walking tour, you’ll venture into some of downtown Chicago's beautiful architectural spaces that remain from the era of the World's Fair. You will play a few thoughtfully designed games, like visual scavenger hunts. Along with guide commentary, photographs and archival materials on shared iPads illuminate the 1893 World’s Columbian Exposition and help us consider why it still captures our imaginations more than 125 years later. 

You can think of this 2.75-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 is great in all seasons. We hope you’ll join us!

Walking Tour Highlights
  • Marvel at colorful mosaics in a hotel built for the 1893 World’s Fair
  • Step into the sweeping grand lobby of Louis Sullivan's Auditorium Building
  • Ride one of the downtown’s last human-operated elevators
  • Discover a secret building hidden in an alley
  • See the Monadnock Building, a landmark early skyscraper
  • Explore 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 snack
  • 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 ($8 for beer, $10 for wine, includes gratuity). At the third drink stop, you may independently purchase a beer, wine, or cocktail of your choice.
  • Dietary Restrictions: One small snack is included. It is vegetarian and gluten-free. If you are dairy-free, or have other allergies, we cannot make substitutions.
  • Tour guide gratuity.
Walking distance: 0.9 mile

  • Duration : 165 Minutes (approx.)
From USD $42.00

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Best Architecture Walking Tour for Design Lovers Book Now Available × × × × × Book Now Available
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

This creative tour for curious people connects architectural styles to other elements of design, art history, and popular culture. In an action-packed 90 minutes, this tour covers Chicago’s vast architectural history, from fur-trappers of early America to Mies van der Rohe’s modernism to contemporary developments. This is not your grandma’s architecture tour! 

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? You will learn about architectural styles through their connections with technology and pop culture. Styles in creations like architecture, graphic design, fashion design, and pop culture have similar qualities when they come from the same era. In order to learn how to contextualize and identify architecture, this tour compares buildings with works from other media like these.

You’ll look at lots of gorgeous buildings while expanding your understanding of architectural styles and Chicago history, right in the heart of downtown Chicago. Tour starts at the Michigan Avenue Bridge, where the city began, and finishes at the new Maggie Daley Park. 

Why is this the “best” architecture walking tour for design lovers? The fun and creative educational approach makes this unlike any other architecture tour in the city. The tour appeals to people looking for an introduction to Chicago architecture, as well as guests who are well-versed in art history

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

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: 0.6 mile

  • Duration : 90 Minutes (approx.)
From USD $25.00

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

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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.

Walking Distance: 1.2 miles.

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

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Century of Contrasts South Loop Walking Tour

Century of Contrasts South Loop Walking Tour

From the Great Chicago Fire to the disco inferno, this curated South Loop walking tour contrasts the social history and architecture of two crucial periods in Chicago history.

Guests will experience incredible architecture among the famed historic districts of Motor Row and Prairie Avenue. Beyond the architecture, guests will discover the unexpected stories of the people who lived and worked in Chicago’s South Loop from 1871 to 1971.

The neighborhood’s Prairie Avenue once boasted “Millionaire Row.” At the peak of the Gilded Age in the late 19th century, some of the wealthiest people in American history built palatial mansions in this bucolic area.

By the 1970s, the neighborhood was spattered with industrial buildings, shuttered train stations, parking lots, and McCormick Place, the just-opened, colossal convention center. Despite this unbecoming state in the 1970s, the choices made and forces unleashed at that nadir of urban decay led to the vibrant and redeveloped neighborhood of today.

1971 was a crucial and overlooked year in Chicago history, a time of transition. City leaders opened America’s biggest convention center, a Modernist corporate acropolis. The roots of the historic preservation movement were taking form mere blocks away. The closure of passenger railroad lines marked the end of an era that defined Chicago’s role in the country, and began the era that we now live in.

Learn the massive histories and inside stories at mom and pop factories and visit both the famous and less-known locations of Chess Records. Guests will learn of the dramatic fall of the mansion district, as beautiful greystones went from high-class soirees to flophouses and publishing offices. This walking tour presents new perspectives on how the South Loop became the vibrant neighborhood it is today.

  • Duration : 105 Minutes (approx.)
From USD $32.00

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