What you'll do:

You'll ride through Chicago's most notorious streets on a guided gangster and ghost tour, hearing the real stories behind the city's darkest history while stopping at landmarks most visitors never find on their own.

• Holy Name Cathedral - Stand at the site of Chicago's most notorious gangland hits and hear the story of the bullets that still mark the church's cornerstone today.

• Harry Caray's Italian Steakhouse - Step inside the restaurant built over Frank Nitti's secret vault, a hidden piece of Chicago crime history hiding in plain sight.

• The Jewelers Building - Explore the former home of Al Capone's speakeasy, tucked inside one of the Loop's most elegant addresses.

• West Couch Place (Death Alley) - Visit the site of the deadliest building fire in U.S. history and hear the chilling account of what happened there.

• The Congress Plaza Hotel - Get the full story on Chicago's most haunted hotel, where guests and staff have reported strange encounters for over a century.

Your expert guide ties it all together with sharp storytelling and details you won't find in any guidebook. By the end, you'll see the city's famous skyline and polished architecture in a completely different light.

Why we love it for your group:

• Luxury Minibus - Travel in a comfortable, climate-controlled vehicle so your group stays together and arrives at every stop ready to explore.

• Expert Guide - Your guide knows Chicago crime and ghost history cold, which means every stop comes with context, not just a quick photo op.

• Iconic Stops - The route covers eight distinct landmarks across the Loop and River North, giving your group a real cross-section of the city's layered past.

• Built for Groups - The private minibus format keeps your group together from pickup to drop-off, no splitting up or waiting for public transit.

• Palmer House Pickup - The tour starts and ends at one of Chicago's most storied hotels, which makes logistics easy no matter where your group is staying.

About this experience partner:

Empire Tours Chicago specializes in guided crime history and haunted Chicago tours for groups looking to go beyond the standard sightseeing circuit. Known for sharp, well-researched storytelling and a fleet of comfortable luxury minibuses, they've built a loyal following among birthday groups, bachelorette parties, and history buffs who want a night out with some substance to it. Their guides bring Chicago's Prohibition-era underworld and its most haunted addresses to life in a way that's engaging for first-timers and longtime Chicagoans alike.

Additional information:

• Expert guide included - A knowledgeable guide leads the full two-hour tour from start to finish.

• Pickup and drop-off - The tour departs from and returns to the Palmer House hotel in the Loop.

• One interior stop - Your group visits the inside of Harry Caray's Italian Steakhouse as part of the tour.

• Group experience - This is a shared minibus tour; guests are grouped with other booked participants unless a private booking is arranged.