Chicago is hands-down one of the most fascinating cities in the world, with a sharp and dramatic history that takes place in the city where Al Capone quite literally built his empire.

From speakeasies and shootouts to shadowy alleyways and illustrious skyscrapers, the Windy City is perfect for anyone who wants a bit of grit with their glamor. To experience it in all its glory, the best way to go is through a proper tour – though many out there are underwhelming.

I’m here to help – I’ve curated a guide to the 3 best mobster tours in Chicago, that will leave your curious mind satisfied and the history nerds fascinated. Let’s jump right in.

Be sure to see our reviews of Chicago Architecture Boat Tours, Chicago River Dinner Cruises and Chicago Food Tours.

Best Mobster Tours in Chicago

	Chicago Crime and Mob Bus Tour	Chicago Night Crimes Tour by Bus	Chicago Mobs and Haunts Walking Tour
Location:	520 S Michigan Ave	163 E Pearson St, Chicago	520 S Michigan Ave, Chicago
Start:	10:00 AM, 12:00 PM, 2:00 PM, 4:00 PM	7:30 PM	7:00 PM
Duration:	1.5 hours	2 hours to 2.5 hours	1.5 hours to 2 hours
Includes:	Luxury, enclosed, temperature-controlled coach bus, souvenir pamphlet	Luxury temperature controlled coach bus, professional tour guide	Luxury, enclosed, temperature-controlled coach bus, souvenir pamphlet
	Tour Information & Booking	Tour Information & Booking	Tour Information & Booking

Quick Answer: The 3 Best Rated Mobster Tours in Chicago For 2025

1. Chicago Crime and Mob Bus Tour
2. Chicago Night Crimes Tour by Bus
3. Chicago Mobs and Haunts Walking Tour

Chicago Mobster Tour Reviews

1. Chicago Crime and Mob Bus Tour

Something that I actually find a bit charming about Chicago is that it doesn’t sweep its past under the rug – rather, it leans into it with a cigar in hand.

The Chicago Crime and Mob Bus Tour will highlight exactly that, offering not some cheesy reenactment, but a deep dive into the darkest stories of the city’s most notorious history.

While it is a bus tour, the vehicle is only there to facilitate transport from point A to point B, ensuring you get to stop and get out to see these sights up close and personally. Clocking in at 1.5 to 2 hours long, this tour is super easy to fit into even the busiest of schedules – more so when you consider that they offer so many different start times!

We met our guide on Pearson, and I knew right away that his caffeinated crime reporter-esque way of speaking promised a real good time. Our luxury coach was super comfortable and spacious, and when you consider Chicago’s rather extreme weather, it’s more than welcome.

We hit all the big names – Capone, Dillinger, Moran, and others – while we cruised past former speakeasies, the site of the St. Valentine’s Day Massacre, and plenty of other interesting spots I’d frankly never know about, otherwise.

With grade-A storytelling, you’ll learn all about the gangsters, crooked cops, and bootleggers who turned illegal booze (at the time) into massive business opportunities! While it’s no doubt entertaining, it’s incredibly educational, with plenty of stories and places you likely won’t have learned about in a history book.

I absolutely love architecture, and it was so interesting learning about how various iconic buildings around Chicago directly related back to the mob – from homes of former mafia members to champagne-bottle-shaped towers.

After the tour, we were so curious we ended up making dinner reservations for the next night at the Harry Caray restaurant site (you’ll learn why!).

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience

2. Chicago Night Crimes Tour by Bus

While Chicago may be fascinating in the daytime, the city after dark becomes even more interesting – especially when it comes to learning about the mob.

The Chicago Night Crimes Tour by Bus is the perfect opportunity to learn about the vice and violence of the Windy City, through the grittiness of one of the US’ most storied metropolises. Lasting about 2 hours or less, it’s an educational yet entertaining way to spend an evening, after dinner.

Starting at 7:30 pm, it’s ideal if you’ve already had dinner and are fueled up for some world-class storytelling and explorations into the griminess just as well as the glitz of Chicago’s mobsters.

Meet up at the corner of N. Michigan and Pearson, hopping on your comfortable, luxury coach, which has full climate control so you’re never too chilly or too hot. The coach also comes with a nice speaker PA system so you can hear your guide sharing interesting stories as you cruise along.

You’ll pass the sites of infamous mob hits, hear about Chicago’s most dangerous neighborhoods during the 20s and 30s, and get a window into the organized crime world that has inspired countless films and TV series.

The night we took this tour, it was foggy, with the ominous white cirrus lingering near the tops of the notorious buildings and around the river, which seemed to transport us back in time.

Learn about incidents like the handshake murder, the Enforcers safe and tunnels, and more, while also getting to “know” leading mobster figures like Capone, Nitti, O’Banion, and other head honchos.

I have to say that while every single stop was interesting in its own way, going into the steakhouse to see Nitti’s Vault, the crime museum, and the historic bootlegging tunnel was really something unique.

Whether you’re a mobster “enthusiast” or would simply like to gain more insight into Chicago’s dark past, this tour should be on your list!

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience

3. Chicago Mobs and Haunts Walking Tour

While there is certainly a place for bus tours, there’s something special about walking at street level, right in the footsteps of the people involved in the legends you’re learning about.

The Chicago Mobs and Haunts Walking Tour is my top pick if you want to go that route – it’s not a challenging walk and feels like you’re almost going on a ghost-hunting trip with your small group and expert local guide.

It’s a bit more laidback, covering some dark subject matter at times, with guides who remain entertaining, passionate, and animated throughout. Even if you don’t consider yourself a mob nor paranormal enthusiast, you’re bound to have a great time if you’re in any way curious about Chicago’s history.

This is easily one of the most educational tours I’ve been on, skipping the more generic stuff that you could learn on any other Windy City tour. I recommend going on one of the other tours first, so you get a good base of mob knowledge, then can relate it back to the ghost sightings and hauntings covered here (not that you need to).

The pace of the tour was just right – never too slow nor too fast – though I do recommend bringing warm clothes during the colder months as it really gets FRIGID!

Start out at the infamous Congress Plaza Hotel (known as one of the most haunted in the US), learning about many horrors that happened here, including the link to a notorious serial killer. Continue on throughout the city, from Grant Park to West Couch Place, as your guide brings the past to life!

If you don’t feel like taking a dedicated “Chicago tour”, but would still like to learn a bit about the more famous sites, this is a great choice. It’s one of the most affordable around, and I’d consider the best “bang for your buck” if you prefer to experience the city on sidewalk-level instead of from behind windows.

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience