Chicago Crime and Gangster Tour

A completely customizable city tour that focuses on all aspects of Chicago’s amazing history, unique architecture, and culture - all you have to do is let us know your specific interests and we will make it happen!

Many will agree that Chicago is not only defined by its iconic skyline, but by its local historic neighborhoods and the people who call them home. The entire vibe of Chicago changes from neighborhood to neighborhood. Whether it is the stately old homes and the massive structures of the white city on site of the World’s Fair in President Obama’s neighborhood of Hyde park or the smiling locals living across the street from Wrigley field, you are sure to get a sense of the old world culture that still exists to this day in Chicago’s many different districts.
This tour includes your own local Historian Tour Guide and chauffeured luxury transportation. This tour has a 4 hour minimum, but can last longer at the client’s request.

Chicago is the birthplace of the modern day skyscraper, many of which rose from the ashes of the Great Chicago Fire over a century ago! The Windy City is home to unique and innovative designs that have shaped American architecture for decades. Although Chicago is the most vertical city from here to Hong Kong, there is great architecture to be seen at the street level as well. From modern marvel skyscrapers such as the Sears “Willis” Tower, to the Gothic designs all along the Magnificent Mile, the thousands of historic beautiful brown stones and the Frank Lloyd Wright Houses of Oak Park, you can be sure there will be something for everyone’s specific architectural tastes. Patrons will also have the unique opportunity to see the amazing hidden architecture and design inside many of these buildings as well.
This tour includes your expert Architect Tour Guide and chauffeured luxury transportation. This tour has a 4 hour minimum, but can last longer at the client’s request.

The Chicago food tour is a culinary touring experience like none other! Patrons will have the rare opportunity to taste famous Chicago cuisine at some of the most famous local, off the beaten path, eateries. Have a Chicago Dog in Wrigleyville, try the Chicago deep dish pizza in Little Italy, and head to China Town for a taste of authentic Chinese cuisine and culture. We can also head to some of the lesser known Chicago neighborhoods with amazing ethnic foods such as Ukrainian Village and Greek Town.
This tour includes your own local Foodie Tour Guide and chauffeured luxury transportation. The price of food is not included. This tour has a 4 hour minimum, but can last longer at the client’s request.

Chicago has no shortage of Haunted History. On this unique and underground haunted ghost tour, guests will have the rare opportunity to visit many of Chicago’s most haunted locations. Visit the old site of the “Murder Castle”, the hotel designed specifically for murdering people in the late 1800s by America’s first mass serial killer H.H. Holmes. There is also the creepy and infamously haunted “death alley” where the charred remains of hundreds of theatre patrons were stacked after perishing in the great fire at the Iroquois Theatre just to name a few. Patrons will also get to enter infamously haunted venues such as the old Congress Hotel, once the full time residence of its former owner Al Capone. This is not a theatrical tour, but rather a historian guided tour with historically documented tales of hauntings told in more of a “camp fire tale” fashion.
This tour includes your own local historian Tour Guide and chauffeured luxury transportation. This tour has a 4 hour minimum, but can last longer at the client’s request.

What is a shopping tour? When it comes to fashion, Chicago is a shopper’s paradise. Hit some of the oldest and most famous shopping establishments in the country with your own person local designer as your tour guide. Our tour delivers exciting perks not available to the regular visitor. Guests will gain special access to designer show rooms, exclusive discounts and rare opportunities to meet local designers. An introduction to new store brands is paired with exploring the beautiful architectural masterpieces which are the shops along Michigan Avenue, the Magnificent Mile. Fashionistas, avid browsers and the curious, will all love exploring Chicago’s best-kept shopping secrets on these guided fashion tours.
This tour includes your own local fashion designer Tour Guide and chauffeured luxury transportation. This tour has a 4 hour minimum, but can last longer at the client’s request.

Looking for a unique way to begin your corporate event, night out in Chicago with friends or bachelor/ bachelorette party? Join our Prohibition Speak Easy cocktail-filled tour and learn about the glamorous and not-so-glamorous Era of Prohibition. Visit the exciting neighborhoods and venues once frequented by notorious gangsters such as Al Capone and Public Enemy Number One, John Dillinger, Many of these old bars in Chicago are still in their original condition as they looked when they opened in the 1920’s during prohibition. Most still have their secret entrances in use today and serve the same cocktails to you over the bars that once catered to infamous Chicago gangsters such as Al Capone’s personal favorite, “The South-side”.
Re-live some of the glamour of the 1920’s and hear stories from the era while delving into rampant racketeering and bootlegging.
Your guide will be wearing 1920’s era clothing. You may do the same or dress in fancy casual attire, as you’ll be visiting some upscale cocktail lounges.
This tour includes your own local Historian Tour Guide and chauffeured luxury transportation. The price admissions and adult beverages are not included. This tour has a 4 hour minimum, but can last longer at the client’s request.