Hell or Heaven? 200 Years of Chicago Gambling

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Hell or Heaven? 200 Years of Chicago Gambling

(1 review)
Chicago, Illinois audio tour: Hell or Heaven? 200 Years of Chicago Gambling
This is a 2.2mi walking tour
It takes an average of 60 mins to complete.
Chicago, Illinois
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$8.99
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About the Tour

Jackpot! Whether you‘re looking to pull the lever or are just curious, this walking tour takes you on an entertaining journey to Chicago‘s only legal casino. Along the way, you‘ll hear about the city‘s 200-year-old love affair with gambling, from seedy dens of vice once known as “hells” to Bally‘s “heavenly” new casino, scheduled to re-open in 2026.

This tour starts and ends a little bit west of the Magnificent Mile. You‘ll walk to Bally‘s construction site, and return via Bally‘s temporary 24/7/365 operation on Ontario Street.

Along the way, I‘ll regale you with local lore about how gambling helped earn Chicago its reputation as the “evilest” city in the world. You‘ll hear amazing stories about the city‘s bygone eras as you walk in the literal footsteps of the con men, crooks, crusaders, and gambling kingpins – not to mention the gangsters, mobsters, and even a few Hollywood stars – who made Chicago famous. You‘ll also hear about the 19th-century Chicago card game which you could never win.

Other highlights include:

  • Standing at the actual location where Capone‘s lieutenants gunned down Scarface Al‘s leading competitor
  • Seeing the street once nicknamed “Hair Trigger Block” when Chicago was the Wild West
  • Visiting Holy Name Cathedral, with its prominent bullet hole
  • Getting to know Chicago‘s gambling lords before Al Capone, including the kingpin who changed horserace bookmaking forever
  • Pausing at some of the famous Chicago night spots that hosted Hollywood types like Frank Sinatra while they operated as clandestine casinos
  • Finding out why Chicago and Illinois finally gave in and legalized gambling

Allow for 1.5 hours for this walk unless you want to stop and gamble. There are plenty of cafes, restaurants and bars along the route for quick or longer non-casino stops. Whether it‘s your first time in Chicago or you‘re a curious local, this tour is a fascinating introduction to the city‘s iconic past.

Categories
Celebrities And Gossip Modern History Local Legends Crime And Mystery

Tour Producer

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Richard Junger

5 tours

Professor, urban historian and former broadcast journalist. Just epublished is my "Real, True Backstories of Old Chicago: As told Day by Day from 1673 to 1925". In it I recount hundreds of the same kinds of Chicago stories as heard in my audio tours, some short and some longer.

Right now only available as an Amazon Kindle ebook (just search for "Backstories of Old Chicago") but a print edition is forthcoming. Meanwhile watch for me on Chicago's streets. I'm the guy who's always asking "guess what happened here?" as I walk with friends.

Preview Location

Location 6

The North Clark Street Gambling District

Turn right at the corner of West Chicago Avenue and keep walking straight.

This area was once known as the North Clark gambling district and police staged occasional raids around here just to give the appearance of being honest. One 1917 raid at a nearby hotel called the T... Read More
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Major Landmarks

  • Temporary Bally Chicago Casino

  • Site of Permanent Bally Chicago Casino

  • Hotel Sofitel Chicago

  • Near to Magnificent Mile

  • The Original Rock 'N Roll McDonald's

  • Short walk along North Chicago River

  • River North neighborhood

  • Ward (A. Montgomery) Park

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Getting There

Route Overview

VoiceMap tours follow a route from a set starting point. It’s how we give turn-by-turn directions and tell a story greater than the sum of its parts.
  1. Start location
    20 E Chestnut St, Chicago, IL 60611, USA
  2. Total distance
    4km
  3. Final location
    N State St, Chicago, IL 60610, USA
  4. Distance back to start location
    94.62m

Directions to Starting Point

The tour starts outside the Hotel Sofitel, 20 E Chestnut St, Chicago, IL 60611-2664. That is two-and-a-half blocks west of Mag Mile Michigan Ave on E. Chestnut Street. Parking is available in several places in the vicinity but is pricey, even on weekends. Going either direction, get off the "L" Red Line subway at Chicago Avenue and walk north two blocks on State Street to Chestnut Street . The Hotel Sofitel is one block over toward N. Wabash Ave. CTA Mag Mile Michigan Ave. street-level buses 143, 146, 147, 148 and 151 all run past E. Chestnut St. Walk two blocks west to the Hotel Sofitel.

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Tips

Places to stop along the way

If you want, stop at the temporary Bally Casino toward the end of the tour and play. There are also other restaurants and bars along parts of the tour including McDonald's original Rock 'n Roll restaurant on N. Clark Street if you don't want to stop at the casino. You can even get a haircut or style on Chicago Avenue, in the River North neighborhood.

Best time of day

From dawn to dusk seven days a week. Casino is open 24/7/365 but outdoor walking is best done in daylight hours. Lake Michigan can be windy at times (Chicago is the Windy City.) Dress for the weather, not the time of year.

Precautions

Safe, but motorists aren't always looking for pedestrians. Watch at intersections, especially for right turns on red.

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