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3/18/24 — 3/20/24 3/18/24 — 3/22/24 3/18/24 — 3/24/24 or
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Loop Interior Architecture Walking Tour × × × × × × ×
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. Much of the tour takes place inside, making it great for any kind of our Chicago weather.

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
  • 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
  • Professionally printed Chicago Pedway map
  • Special Chicago gifts
  • Discounted flat-rate parking at Grant Park North Garage ($15)
Walking distance: 0.7 mile

  • Duration : 90 Minutes (approx.)
From USD $28.00

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1893 World's Fair Tour with Bars × × × × × × ×
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 2.5-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 drink during the tour at the Berghoff at check-in ($8 for beer, $10 for wine, includes gratuity). The tour concludes in a hotel with several bars where you may independently purchase a beer, wine, or cocktail of your choice.
  • Dietary Restrictions: One small snack is included. It is vegetarian. If you are dairy-free, or have other allergies, we cannot make substitutions.
  • Tour guide gratuity.
Walking distance: 0.9 mile

  • Duration : 150 Minutes (approx.)
From USD $38.00

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Historic Chicago Walking Bar Tour × × × × × × ×
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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A Day at the 1893 World's Fair × × × × × × ×
A Day at the 1893 World's Fair

A Day at the 1893 World's Fair

You're invited to the World's Columbian Exposition! How will you get there? How much are tickets? Where do you go to the bathroom?! This one-hour virtual event will share the ins and outs of a typical day at the 1893 World's Fair.

You're invited to the World's Columbian Exposition! How will you get there? How much are tickets? What was for lunch? What's the bathroom like?! This one-hour virtual event will share the ins and outs of a typical day at the 1893 World's Fair. 

  • A passionate event host shares the people, places and ideas from the World’s Fair.
  • You’ll view historic photos, etchings and prints.
  • Includes 3D recreation of riding the ferris wheel. 
These virtual events are a great way to safely connect with friends and family from afar. 


We usually only offer this event for private groups starting at a flat rate of $475. We are offering this one-time opportunity for the public to join us for FREE as we fundraise for this charitable project with the Design Museum of Chicago. 

AFTER YOU REGISTER YOU WILL RECEIVE A CONFIRMATION EMAIL WITH THE ZOOM LINK. 

A recording of the event will be available for up to 3 days afterwards as we will be doing our last fundraising push to meet our goal! Thank you in advance. 


  • Duration : 60 Minutes (approx.)
From USD $0.00

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