Chicago, Illinois audio tour: Chicago’s Ragtime & Jazz Eras: Stories of Al Capone & the Everleigh Sisters

Chicago’s Ragtime & Jazz Eras: Stories of Al Capone & the Everleigh Sisters

Walking Tour

45 mins

About the Tour

Ever wanted to walk in the footsteps of major league gangsters with colorful nicknames like Al “Scarface” Capone, Frank “the Enforcer” Nitto, or “Greasy Thumb” Jake Guzik? How about big time flesh peddlers and saloon keepers like the Everleigh sisters, Victoria Shaw, or Mickey Finn? On this walking tour, you’ll go back in time to Chicago’s ragtime and jazz eras to do exactly that. Along the way, you’ll hear stories about the assorted pimps, procurers, madams, and slumlords who ran the ill-famed Levee Red Light vice district, and the bootleggers, traffickers, card sharks, hoodlums, gunmen, and crooked cops and politicians who made up what was known as the “Chicago Outfit.”

This circular walk takes you through Chicago’s Motor Row and Prairie districts, leading you to or telling you about sites including:

• Saloons like the original Bucket of Blood and Mickey Finn’s
• Brothels and bagnios, both posh and fleabag
• Speakeasies like Al Capone’s Four Deuces and Hymie Jacobs’
• A dance hall which served as the center of a vast white slave trade
• Several of Capone’s “headquarters” including the infamous Lexington hotel
• Hourly hotels that catered to transient sex workers who were known as “roomers”
• Capone’s Depression-era “soup kitchen” for the unemployed

No soup kitchens for you! There are plenty of cafes, restaurants and bars along this 1.5 mile trip for quick or lengthier stops, and Chinatown is a few blocks away.

Join me on this tour and discover why early twentieth-century Chicago had the largest Red Light vice district in the entire world, and the most notorious Prohibition gangsters and mob connections!

Tour Producer


Richard Junger

Professor, urban historian and former journalist. Most recent book is "Becoming the Second City: Chicago's Mass News Media, 1833-1898" from University of Illinois Press. I'm the guy who says "guess what happened here?" as I walk around Chicago with friends.

How VoiceMap Works

Focus on your surroundings, not the screen

VoiceMap’s audio tour app uses GPS to play audio automatically, at the right time and place. Just install it, then download your tour and go to the starting point to begin your walk, drive, cycle, train trip or even boat ride.

Follow a route with turn-by-turn-directions

Tours follow a route from a fixed starting point. This is how we provide turn-by-turn directions. It also helps publishers tell a story greater than the sum of its parts. But you can use Resume to pick up a tour from the closest location whenever you like.

Listen as many times as you like

You can listen to your tours as often as you like using both the VoiceMap app and the VoiceMap website. Your access to tours doesn’t expire.

Take virtual tours anywhere

Just select Virtual mode in the VoiceMap app to listen to tours at home – or anywhere else. You’ll see the option after you download the tour. You can also listen to the whole tour here on the website.

Buy for less on and sync

Once you’ve purchased a tour, it’s added to your VoiceMap library. If you sign into the app using the same method you used on the website, you’ll have access to your full library of tours in both places.

Use VoiceMap offline

The VoiceMap app works entirely offline if there’s no data connection, so you don’t have to pay roaming fees. Just download the tour over WiFi before you get started.

Major Landmarks

  • Chinatown

  • McCormick Place

  • Wintrust Area

  • Soldier Field

  • Museum Park

Directions to Starting Point

For GPS purposes, use the address of 2 W. Cermak Road, Chicago, IL 60616, as your destination. The tour begins and ends near the Chicago Transit Authority Green Line Cermak-McCormick L station at 12 E. Cermak Road. There is hourly on-street parking in the immediate vicinity of the station at the cheapest posted rate in the city. In particular, the southern side of Cermak just to the east of the station often has open parking because it fronts an empty lot. Parking may or may not be available in other locations along and near the tour route, but spots may not be available weekdays and cost more per hour.

The Green Line Cermak-McCormick L station is roughly in the middle of the line, a few stops south from the Loop. The Cermak-Chinatown Red Line L station at 140 W. Cermak, is three blocks west of the starting point and a few stops south of the Loop as well.

The tour's starting and stopping points are six-or-so walking blocks from the McCormick Place North building, a few blocks closer from many of the McCormick-area hotels. Use the 2 W. Cermak Road address as your GPS destination point.

The Metra Electric line McCormick Place stop is about a six block walk from the starting point. The South Shore commuter line will stop at the same McCormick Place stop, but it is best to check with a conductor ahead of time and tell them that you want to get off there.

Show Directions
Buying for somebody else?
If you’d like to give VoiceMap tours as a gift, you have two options: choose the tours yourself, or buy a voucher redeemable against any of VoiceMap’s tours in 167 cities worldwide.
Buy a gift voucher
VoiceMap tours for large groups
If you’d like to provide groups of guests with access to a VoiceMap tour, you can buy a specific number of copies for a particular event or obtain a license for more regular use.
Find out more


Places to stop along the way

There are several small restaurants and bars along parts of the route, but many specialize in take-out food only. There is a nice sit-down White Castle restaurant in the middle of the tour. For more sit-down dining, walk a couple of blocks east along Cermak toward the hotel district west of McCormick Place or walk six blocks west to Chinatown, which has many takeaway and sit-down dining locations and shops.

Best time of day

Dawn to dusk seven days a week. The tour passes through residential areas and past a school, so the route may be busier at certain times of the day. The route is about one mile west of Lake Michigan and cold winds and lake-effect snow can still make the walk chilly in the late fall, winter, and early spring. Check the weather forecast.


The route is safe but be aware of traffic as Cermack, Michigan, State, and other streets are busier daytime thoroughfares. Most of the tour goes past small shops, restaurants, and offices, but a few blocks are through residential and warehouse areas and past a school.


Preview mode limited to first 3 locations.
Chicago’s Ragtime & Jazz Eras: Stories of Al Capone & the Everleigh Sisters