A note on this page: we're actively setting up a formal partnership with this tour operator. Until that's confirmed, the link below goes straight to their own site — a plain, honest link, not a tracked one. We'll update it the moment the partnership is live, and you'll never pay more either way.
Chicago's Loop has two overlapping reputations: it's where Al Capone's Prohibition-era empire actually did business, and it's where a lot of the city's best ghost stories come from — often at the exact same buildings. The Gangsters and Ghosts walking tour, run by Empire Tours & Productions, leans into both at once instead of picking a lane, walking roughly a mile and a half through the Loop and South Loop over about two hours with a guide who's a historian first, not a costumed actor.
What's Actually On the Tour
Length
About 2 hours, covering roughly 1.5 miles on foot through the Loop and South Loop — a real walk, not a bus ride, so wear shoes you can stand a stretch in.
The Angle
This isn't a split "gangster tour" and "ghost tour" — it's one tour that tells both stories at the same stops, since a lot of Chicago's most notorious crime-era buildings are also the ones with the most persistent ghost stories attached.
The Guide
Led by a historian rather than an actor in costume — the format leans toward real history with ghost lore woven in, not a haunted-house-style jump-scare experience.
Who It's Through
Run by Empire Tours & Productions, which also operates a same-branded "Gangsters & Ghosts" tour in New York — a separate product covering different sites, not this one.
Stops & Stories You'll Hear About
Congress Plaza Hotel
Widely cited as one of Illinois's most haunted buildings — and separately tied to Al Capone, who's said to have used it as a base.
Death Alley
A narrow Loop passage with a reputation stretching back over a century as both a gangster meeting spot and the source of real ghost stories.
Palmer House
Described on the tour as a gangster-era meeting point during Chicago's Prohibition years.
The Chicago Riverwalk & Chicago Theatre
Both named as stops carrying their own ghost legends alongside the broader Loop history.
The throughline is Chicago's Prohibition-era "vice district" — speakeasies, bootlegging, and the smugglers' tunnels that supposedly ran beneath it — with names like Al Capone, Bugs Moran, and John Dillinger coming up along the way.
Worth Knowing Before You Book
- Pricing varies by where you book. Different ticketing platforms list this tour anywhere from around $32 to $44 per adult (with youth and senior pricing on some), and the operator's own site doesn't post a fixed price — check the actual total at checkout rather than assuming one figure.
- Several daily departures are commonly listed — around 11am, 1pm, 4pm, and 8pm — plus a seasonal late-night Halloween departure. Confirm the current schedule when you book, since it isn't posted on the operator's own site either.
- The most frequently cited meeting point is near 71 E Wacker Dr, by the Royal Sonesta Hotel at Wacker & Wabash — but double-check your exact meeting spot on your actual ticket, since it can vary by booking platform.
- This is a different company from "Inside Chicago Walking Tours," which runs its own similarly-named true-crime/ghost tour in the city — worth knowing so you book the one you actually mean to, since the names and subject matter overlap closely.
- It's a walking tour in all weather — unlike a river cruise, this one doesn't shut down for the season, but dress for whatever Chicago's doing that night.
Pair It With
The Loop stops on this tour sit close to a lot of the city's other after-dark options — a River North or South Loop dinner reservation, a nightcap near the Palmer House, or one of our other seasonal picks if you're building a full haunted-Chicago evening.
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Same Company Also Runs a River Cruise
Empire Tours & Productions, the operator behind this walking tour, also runs Chicago's architecture river cruise — a daytime-friendly way to see the city from a completely different angle.
See the Architecture Tour Guide →
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