Three Must See Sites for Chicago Architecture

There are an enormous range of reasons to take a tour of Chicago’s stunning architecture. Not only is it a greatly enriching experience from a cultural standpoint, but it’s also a huge opportunity to get to enjoy some of the finest aesthetics the city has to offer and enjoy the beauty of astounding architectural design and implementation! Whether you are seeking a tour guide with expertise on the finest details of Chicago’s architecture, variety, or flexibility, you can’t go wrong with a tour of these great architectural sites. Here’s some additional information on touring Chicago’s fantastic architecture!


#1 The Chicago River

The first and one of the most impressive sites for Chicago architecture is none other than the Chicago River. The Chicago River is a stunning system of canals and rivers which, when combined, adds up to a length of over 156 miles! Not only is that an impressive reality in and of itself, but the Chicago River is the site of some of the most impressive infrastructure and artificial structures in all of America.


If you’re looking for a great place to start on your knowledge and experience of Chicago’s architecture, you really can’t go wrong with the Chicago River!


#2 The Willis/Sears Tower

Holding the title of the world’s tallest building for almost 25 years, the Willis Tower (commonly referred to as the Sears Tower due to its original name) is truly one of the most impressive examples of architecture in all of Chicago. Designed by Fazlur Rahman Khan, the Willis Tower is considered one of the most groundbreaking achievements in the history of American architecture!


With that knowledge, how could anyone not have an interest in touring this truly stunning example of Chicagoan architecture? Touring the Willis/Sears Tower is not only an experience that you will remember for the rest of your life, but it’s also a great way to advance your understanding of both architecture and the city of Chicago. Thus, a tour of the tower can really be seen as a crucial experience in understanding and appreciating Chicago architecture.


If you still have any doubts, just keep in mind: This is one of the tallest buildings in the world! That fact alone should be enough to compel just about anyone to at least consider a tour of the tower. After all, what’s more exciting than seeing one of the tallest buildings in the world?


#3 The Magnificent Mile

Another great site for touring Chicago’s architecture is the Magnificent Mile. Part of Chicago’s Michigan Avenue, this section of the city is a fantastic display of the ingenuity, vision, and craftsmanship of Chicago’s great architects. Given its name by the Rubloff Company in the 1940’s, the Magnificent Mile has really got it all: Shops, hotels, museums, and more!


Anyone who has an even passing interest in Chicago’s architecture will find it hard to resist the sheer magnetic appeal of the Magnificent Mile. It is truly and incontrovertibly one of the best, brightest and most impressive architectural features Chicago has to offer!

Chicago’s #1 Gangster and Ghost Tour

Chicago Gangster and Ghost Tours

If you’re visiting Chicago, you can’t truly experience the city without immersing yourself in the criminal history of the gangster town. What better way to learn about the city’s shady past than by tracing the footsteps of its most notorious gangsters on a Chicago Walking Tour? Get transported back in time to experience Chicago as it was lived by locals during the bootlegging gangster reign of the 1920s.

Our 1.5-mile Chicago Gangster Tour guides you through the locations where some of the most memorable events in Chicago’s history occurred. Fancy a stop at the Chicago Congress Hotel where Al Capone ran his bootlegging operations incognito? Perhaps you’ll be lucky enough to spot a glimpse of his ghost stalking the halls. Our historian guides will dish up the details of Scarface’s colorful tenure in Chicago as he turned increasingly violent towards his gangster competitors whilst making a fortune throughout Prohibition. A divisive figure, he is lauded for his impressive ability to provide people with banned substances and also condemned for his remorseless nature. Our Chicago Gangster Tours and Chicago Crime Tours use compelling information and settings to show how Al Capone became a central figure in American criminal folklore and a crucial piece of Chicago’s historical character.

Accurate information is provided. In addition to gangsters like Al Capone, Chicago is known for its infamous fires. You won’t find many buildings older than 1871, when the Great Chicago Fire swept through the city and destroyed most of it. But perhaps a lesser known fire, though appalling in its result, was the 1903 Iroquois Theatre fire. The new theatre was packed with guests and stage performers enjoying an Eddie Foy matinee when a stage light caught fire. The building was soon engulfed, and hundreds of people were trapped inside. Over 600 people lost their lives. The alley behind the theater, now known as the Oriental Theater, has been dubbed “Death Alley” because of the unusually high sightings of ghosts and apparitions in the area. If you’re interested in Chicago Ghost Tours, Death Alley will raise your hair with the sense of someone else’s presence.

The Chicago Congress Hotel is also a grand piece of architecture filled with hauntings and unearthly sensations. Rumors abound about the strange happenings within Plaza. Take a Chicago Ghost Tour, if you dare, to find out for yourself whether all the talk is true!

No Chicago Ghost Tour or Chicago Crime Tour would be complete without a reference to notorious serial killer Dr. H.H. Holmes, recently returned to the public eye once again by The Devil in the White City, written by Erik Larson. Discover the creepy true story of how Holmes constructed a three-story “Murder Castle” in 1892. Though it fronted as a pharmacy, apartments, and retail space, H.H. Holmes actually built a labyrinth with chutes, trapdoors, and a crematorium where he trapped and murdered an unknown number of women before he was caught and hung for his despicable crimes.

Embarking on a walking tour through the Chicago Loop Vice District setting will certainly help you appreciate the characters and events that made Chicago grow into the city it is today.

The Congress Hotel…Al Capone’s Old Haunt?

CHICAGO — The Congress Plaza Hotel has been named the most haunted spot in Illinois.

The hotel at 520 S. Michigan Ave. is supposedly the home of a number of ghosts — including that of notorious gangster Al Capone, according to Travel + Leisure magazine, which picked the most haunted spots in the United States.

The Congress also is reported to be the home of ghosts Karel Langer, a young boy who runs around the halls, and Peg Leg Johnny, who plays with the light switches, according to WBEZ. And the hotel supposedly inspired Stephen King’s horror story,“1408.”

Tour Chicago With Us

Chicago Private Tours and Productions

Here at Chicago Private Tours and Productions, we specialize in providing Chicago visitors, tourists, and locals with unique and exclusive tours, experiences, and insight today. We work with you to create your own custom Chicago private tour, bespoke experiences, corporate events, and any other tailor-made Chicago tour your heart desires.

We offer specialized private tours of Chicago, handcrafted to highlight the best attributes, historical elements, and notable spots in the city. Our production team can help you develop:

  • Chicago food tours
  • Dining events
  • Themed parties
  • Distinctive occasions
  • Celebrations

And the list goes on. We work with private, small, large, and corporate group sizes today.

It is our goal to arrange an experience that reflects the connection between your interests and all that our Chicago tour company can offer you. The sky is the limit!

Our Guarantee

Here at Chicago Private Tours and Productions, we guarantee:

  • Special Access: Gain access to unique venues that are sequestered from the general public through our private Chicago tours.
  • Local Perspectives: Meet with Chicagoans who love to share the secrets of their city.
  • Personal Concierge: We offer full-service concierge support for all of your transportation requirements.
  • Custom Private Tours: All of our private Chicago tours come with a specialist tour guide, private luxury transportation, and a chauffeur. Tours contain frequent stops and some walking, if it suits the customer. All of our tours begin at $165 per hour, with a 3-hour minimum.


  • Architecture of Chicago Tour
  • Chicago Foodie Tour
  • The Speakeasy Pub Crawl
  • Custom City Tour
  • Neighborhoods of Chicago Tour
  • Magnificent Mile Shopping Tour
  • Gangsters, Mafia, and Crime Tour
  • Haunted History Tour

The Bespoke Chicago Experience

Our bespoke Chicago tour experiences are made from scratch with each and every one of our patrons in mind. Our goal is to curate something uniquely memorable for you and your party that will really resonate with your group.

Some examples of our custom Chicago private tours include:

  • Dinner parties at Al Capone’s Old Suite at Congress Hotel
  • Shopping on the Magnificent Mile with a local fashion designer
  • Batman’s Penthouse parties

Our special events and productions team can provide your board of directors, clients, and colleagues with a unique experience they will never forget. Some of our notable corporate Chicago events include:

  • Exclusive rooftop parties
  • Chartered super yachts along the Chicago River and Lake Michigan
  • Prohibition themed parties in old speakeasies

We want to work with YOU! We want to plan your perfect private Chicago tour or corporate event, no matter the party size.


Phone: 1-708-613-5400


The Windy City’s Architecture

The buildings and architecture of Chicago have influenced and reflected the history of American architecture. The built [constructed] environment of Chicago is reflective of the city’s history and multicultural heritage, featuring prominent buildings in a variety of styles by many important architects. Since most structures within the downtown area were destroyed by the Great Chicago Fire in 1871 (the most famous exception being the Water Tower) Chicago buildings are noted for their originality rather than their antiquity.

Chicago is world-famous for its plethora of unique architectural styles, from Chicago Bungalows and Two-Flats to the grand Graystones along Logan Boulevard and Lawndale Avenue, from the skyscrapers of the Loop as well as a wealth of sacred architecture such as the city’s ornate “Polish Cathedrals”.