The Staypineapple Hotel in Chicago: A Story About Prohibition, Al Capone, and One Infamous Dentist

Upon walking into The Staypineapple Hotel (formerly called The Alise) in Chicago,  you would be hard pressed to believe there is any other side to this distinctively upbeat boutique hotel.   For starters, a huge crocheted pineapple seems to greet you from the window as the age-old symbol of wealth and welcome adopted by hotel owner and operator, the Staypineapple Hospitality Corporation.

Cheerful pineapple-yellow accents are everywhere, from the artwork to the free bike rentals that are ready and waiting for you to explore the city’s landmarks from this perfectly situated spot in the central Loop. There’s a stuffed husky mascot that sits on every bed in the 122 guest rooms, next to a suggestive pineapple pillow with the embroidered words, “Sleep with me.”

There are even pineapple cupcakes in the lobby every afternoon, with pineapple-infused water to wash them down. You can’t help but smile. But as you walk through the lobby you begin to notice the wrought iron railings, the rich mahogany doors, and the marble mosaic floor tiles. The original hydraulic elevator, though refurbished, is clearly from a different time. Instead of a magnetic card, you are handed a real metal key, etched with your room number. As you insert the key into the doorknob of your room you see the word “Reliance” carved in it and wonder why. Perhaps the cheerful exterior of The Staypineapple Hotel Chicago is just that: an exterior.

Like the history of Chicago itself, the story of the hotel seems to be so much more. It’s an iconic, bold, and truly American story. But the undercurrent of subterfuge, darkness, and murder is a constant whispered undercurrent. You can’t deny it’s a part of the hotel’s history, a history that is uniquely Chicago.

A Hotel Was Never the Plan


In the late 1870’s and early 1880’s commercial real estate in Chicago was booming in the wake of the Great Chicago Fire of 1871 and as the country bounced back after a seven year economic depression. William Ellery Hale was the founder of the Hale Elevator Company, one of the first manufacturers of hydraulic elevators as cities began envisioning and constructing “skyscrapers.” In 1880 Hale purchased an existing building on West Washington Street in the heart of the burgeoning Loop. The building was currently in use as a bank with renters living on the second, third and fourth floor apartments above but Hale envisioned a “tower” in that spot, showcasing one of his latest elevator designs. He bought the property and, when the renters didn’t want to terminate their leases early, he hoisted the second through fourth floors up on jackscrews and ordered the first floor and basement to be demolished.

When the leases were up and the tenants moved out, Hale commissioned the Chicago-based architecture firm of Burnham & Root to design his vision. Daniel Burnham and John Wellborn Root were well known and respected throughout the city but were about to become architects for the ages for their design of the Chicago World’s Fair fairgrounds. While immersed in work for the fair, John Wellborn Root designed Hale’s ground floor and basement and had begun work on the rest of the building’s design when he prematurely died of pneumonia in 1891. Drowning in work on the World’s Fair and struggling to overcome his grief over the loss of his partner and friend, Daniel Burnham hired Boston-based architect Charles Atwood to complete the rest of Hale’s vision, as Root’s initial plans became forever lost in the wake of his death.

In learning that Hale intended the building to be used as office space for physicians and dentists while also being a unique part of the Loop’s new skyline, Atwood created a 14-story building with expansive glass windows to let in as much natural light as possible. Meanwhile, he designed the building’s exterior walls to be constructed from white terracotta. Windows this large were expensive to produce but Atwood’s thinking was that they would allow for the maximum amount of natural light to enter the office spaces, making for better visibility during medical and dental exams in an age of coal dust and gas lighting.

The white terracotta exterior was a material that had never been used in the construction of previous Chicago buildings but would continue to be used by Atwood for the buildings of the Fairgrounds to give the impression of cleanliness and purity, which he also thought would be advantageous to doctors and dentists. The building was completed and named the Reliance Building in 1895, with its first tenant being a dry goods store on the ground floor. Over the course of the next few decades, other merchants and medical and dental professionals would occupy the ample space and the Reliance became one of the first skyscrapers in Chicago to offer electricity and telephones in all of its offices.

Prohibition, Al Capone, and One Infamous Dentist

The Reliance Building led an innocuous life of providing office space to health care providers until Prohibition in the 1920s and the rise of gangster-related crime. As Prohibition prohibited the sale and consumption of alcohol, illegal speakeasies run by gangsters like Al Capone and his Chicago Outfit, which came to dominate the city, sprang up everywhere. Capone not only controlled the speakeasies but the gambling houses, brothels, night clubs and breweries as society rebelled against Prohibition using the very vices it sought to eliminate.

Leading a double life was not unheard of, as milkmen by day became speakeasy bartenders by night while others (policemen and politicians included) aided and abetted the gangsters that were the spiders at the center of this corrupt web. It was not uncommon for gangsters to also have a doctor in their back pocket to supply them with drugs for the burgeoning narcotics trade as well as lend their knowledge of chemistry for the use of explosives.

As he would have you believe, Dr. Frank Brady was a dentist whose offices where housed in room 809 of The Reliance Building. But, in addition to pulling teeth and filling cavities, “Dr. Frank” was also Al Capone’s narcotic connection. When Al had a toothache (and he seemed to have them regularly) he stopped by Dr. Frank’s office for treatment and would leave with more than a few aspirin for pain relief.

This relationship continued for almost a decade until 1929 and the infamous St. Valentine’s Day Massacre, in which several gangsters in Bugs Moran’s rival gang were murdered by members of Capone’s gang on February 14th. As the story goes, the police questioned Dr. Frank about his most regular (and most infamous) patient as they investigated the massacre. Though no one knows if the good dentist betrayed the mob boss or not, it was clear that Al couldn’t afford to care.

On April 29th, 1929, two members of Al’s gang broke into Dr. Frank’s office and, in broad daylight with patients throughout, shot Dr. Frank to death. The police and newspapers were quick to discover the dual nature of Dr. Frank’s practice and, in addition to providing narcotics, it was unveiled that he had also developed an acid that erased the numbers and letters on stolen checks, bonds, and stock certificates. The Reliance Building earned its place in the annals of Chicago infamy that day and so did Dr. Frank Brady.

The Fall Before the Rise

When Prohibition ended and the Great Depression began the Reliance started to have trouble keeping its numerous offices occupied. Most Chicagoans’ struggle to survive simply left no spare money for preventative health care or even treatment and many of the building’s offices remained empty for the better part of a decade.

Even after the Great Depression and WWII ended, the Reliance’s small offices were becoming old and out of date. In 1970 the National Park Service listed the Reliance Building on its National Register of Historic Places and, in 1976, it even became a National Historic Landmark.  However, the building’s upper floors continued to remain largely unoccupied and it fell into disrepair. After years of disagreement in City Hall about what to do with the building, the city of Chicago purchased it in 1994 and restoration of its unique terracotta and glass exterior began.


This process took four years and $27.5 million, with the city selling the property during the renovation to Canal Street Partners, LLC, who began remodeling the interior into a boutique hotel. Kimpton Hotels took over and completed the renovations in 1999. The Reliance now had a new name and a new identity as the Hotel Burnham, honoring one of the visionaries that created it.

A New Name, An Old Story


In 2016 Kimpton Hotels sold the Hotel Burnham to the Staypineapple Hospitality Corporation, which gave the hotel its unique pineapple-themed touch and the name  which was also the name of their successful San Francisco hotel.  21st century amenities such as free bike rentals for exploring the city, pet friendly accommodations, and structuring almost all the guest rooms to have a view of Chicago landmarks like Millennium Park, the Chicago Theater, and Lake Michigan were initiated.

In keeping with the building’s historical significance, Staypineapple also agreed to have the hotel be part of several local historical tours and guests and visitors alike marvel at the distinctive terracotta exterior, the Florentine glass and mahogany guest room doors that still evoke the appearance of an office, and the wrought iron and marble staircases.

The juxtaposition of old and new is not novel in cities these days as we seek to preserve and modernize at the same time. But only in Chicago can infamy and history blend into a story that will forever intrigue.

StayPineapple Chicago
1 W. Washington Street
Chicago, IL, 60602


Read reviews, compare prices, and book on TripAdvisor

More Stories
The Algonquin Hotel New York: Literary Legends Know Why The Caged Bird Sings