When you think of Chicago, what comes to mind? Deep-dish pizza, championship sports teams, and a vibrant cultural scene might top your list. But there’s something else that truly sets the Windy City apart: its breathtaking architecture.

Chicago isn’t just another skyline—it’s a living museum where each building tells a story of innovation, resilience, and artistic vision. From the pioneering skyscrapers that rose from the ashes of the Great Chicago Fire to cutting-edge contemporary designs, the city’s architectural landscape offers an unparalleled journey through American history and creativity.

The Loop: Where Modern Architecture Was Born

The heart of Chicago’s architectural wonders lies in the Loop—downtown’s bustling core where historical landmarks stand shoulder-to-shoulder with modern marvels. Here, the Chicago School of architecture revolutionized building design following the Great Fire of 1871, introducing steel-frame construction and expansive glass windows that would forever change skylines worldwide.

Walking through the Loop is like stepping through different chapters of architectural history:

• The Rookery Building showcases the genius of both Daniel Burnham and Frank Lloyd Wright, with its stunning light court that blends old-world charm with modernist touches.
• The Chicago Board of Trade Building stands as an Art Deco masterpiece, its stepped-back design topped with the statue of Ceres, the Roman goddess of grain—a nod to Chicago’s commercial roots.
• Willis Tower (formerly Sears Tower) once held the title of world’s tallest building and remains an iconic symbol of the city’s ambition.
• The Chicago Cultural Center dazzles visitors with its stunning Tiffany glass domes and exquisite Beaux-Arts detailing.

Want to explore these architectural gems and more? Our Chicago Loop Architecture Tour takes you on a journey through time, revealing the stories behind these magnificent structures and the visionaries who created them. From Chicago School pioneers to modernist masters, you’ll discover how this city became a laboratory for architectural innovation.

The Riverwalk: Where Urban Design Meets Nature

Chicago’s relationship with its river has evolved dramatically over the centuries—from industrial lifeline to recreational oasis. Today, the Chicago Riverwalk stands as a testament to thoughtful urban planning, offering both a stunning perspective on the city’s architecture and a peaceful retreat from urban bustle.

A stroll along the Riverwalk rewards you with breathtaking views of:

• Marina City’s iconic “corncob” towers, designed by Bertrand Goldberg, that revolutionized urban living
• Merchandise Mart, once the largest building in the world, showcasing the grandeur of Art Deco design
• Wrigley Building’s gleaming white terra cotta façade, inspired by the Giralda tower in Seville
• Tribune Tower’s neo-Gothic details and its collection of embedded stones from famous structures worldwide
• 150 N. Riverside, a modern marvel that seems to defy gravity with its narrow base

Our Riverwalk, North Loop Walking Tour offers the perfect introduction to this architectural showcase. As you wander along the river, our knowledgeable guides will help you appreciate not just the buildings themselves, but how they interact with the surrounding environment and reflect Chicago’s evolution from a gritty industrial hub to a vibrant, forward-thinking metropolis.

River North: From Warehouses to Wonder

Just north of the river lies one of Chicago’s most dynamic neighborhoods: River North. Once dominated by factories and warehouses, this area has transformed into a vibrant district of galleries, restaurants, and striking architectural contrasts.

River North’s architectural character showcases Chicago’s talent for adaptive reuse:

• Former industrial spaces now house thriving art galleries and tech startups
• Holy Name Cathedral’s Gothic Revival spires stand in contrast to sleek glass towers
• 330 N. Wabash (formerly IBM Building) represents Mies van der Rohe’s modernist vision
• Carbide and Carbon Building gleams with its dark green and gold Art Deco styling
• Contemporary structures like Aqua Tower with its undulating balconies push design boundaries

The neighborhood perfectly illustrates Chicago’s knack for honoring its past while embracing innovation—a theme you’ll encounter throughout our walking tours.

Why Chicago Architecture Matters

Chicago’s architectural significance extends far beyond aesthetic appreciation. The innovations developed here—from the first skyscrapers to sustainable green buildings—have influenced urban development worldwide. When Louis Sullivan declared “form follows function,” he wasn’t just creating a catchy phrase; he was establishing a philosophy that would guide generations of architects.

The city’s buildings reflect its history, values, and aspirations. The soaring skyscrapers speak to ambition and progress. The preserved landmarks demonstrate respect for heritage. The thoughtful integration of green spaces reveals a commitment to livability. Together, they create a cityscape that’s not just beautiful, but meaningful.

Experience Chicago Architecture Firsthand

Reading about Chicago’s architectural wonders is one thing—experiencing them in person is something else entirely. Nothing compares to standing beneath the towering Tribune Tower, feeling dwarfed by its neo-Gothic grandeur, or gazing up at the perfect geometric harmony of a Mies van der Rohe creation.

Our walking tours offer more than just facts and figures. They provide context, stories, and insights that bring these magnificent structures to life. From the scandalous tales behind certain buildings to the revolutionary techniques that made them possible, you’ll gain a deeper appreciation for Chicago’s architectural legacy.

Whether you’re a dedicated architecture buff or simply someone who appreciates beauty and innovation, our Chicago Loop Architecture Tour and Riverwalk, North Loop Walking Tour offer unforgettable journeys through one of the world’s most architecturally significant cities.

Join us as we explore the buildings that don’t just shape Chicago’s skyline—they tell its story.

Introduction

Welcome to Chicago’s infamous gangster history! This self-guided walking tour will take you through approximately one mile of the Windy City’s most notorious neighborhoods, revealing the dark and fascinating criminal past that helped shape Chicago’s identity. The tour focuses primarily on the North Side and Loop areas where much of the city’s gangland activity took place during the Prohibition era and beyond.

Tour Length: Approximately 1.8 miles
Duration: 90-120 minutes
Start Point: Old Water Tower/Jane Byrne Plaza (Michigan and Chicago Ave)
End Point: Federal Plaza (Jackson and Dearborn St)
Google Maps: Crime & Gangster Tour Route

Prefer to join a guided tour? Check out our schedule and book your Crime and Gangster tour online: Chicago Crime & Gangster Tour

Stop 1: Old Water Tower/Jane Byrne Plaza

Location: Michigan Avenue and Chicago Avenue

Begin your tour at Chicago’s historic Old Water Tower, one of the few structures to survive the Great Chicago Fire of 1871. This limestone tower, built in 1869, originally held a huge pipe containing Lake Michigan water for firefighting. When the Great Fire destroyed most of the city, this tower remained standing and became a symbol of Chicago’s resilience.

This neighborhood was once the territory of Dean O’Banion, an important figure in Chicago’s criminal history. Born in 1892, O’Banion grew up in a dangerous neighborhood called Little Hell and ran with the Market Street Gang. Initially a safecracker and burglar, O’Banion eventually controlled the bootlegging operations in Chicago’s North Side during Prohibition, which began in January 1920 when the National Prohibition Act (Volstead Act) became law.

O’Banion and his North Side Gang competed with Johnny Torrio and Al Capone’s South Side operation, creating tensions that would eventually erupt into the deadly “Beer Wars.”

Walking Directions to Stop 2: Head west on Chicago Avenue, then turn south onto State Street. Walk to 730 N. Wabash Ave.

Stop 2: Holy Name Cathedral

Location: 730 N. Wabash Ave (stop on State Street side)

Holy Name Cathedral, dedicated in 1875, is not only a beautiful church but also a site with deep connections to Chicago’s gangland history. Across the street once stood Schofield’s Flower Shop, where Dean O’Banion worked as part owner. The flower shop provided O’Banion with a legitimate business front for his bootlegging operations.

Despite his reputation as a ruthless killer (allegedly responsible for about 25 deaths), O’Banion was known for his friendly demeanor and always wore a flower in his lapel. His bootlegging empire was incredibly lucrative, particularly in this wealthy area of the city.

In 1924, relations between O’Banion’s North Side Gang and Torrio/Capone’s South Side operation deteriorated rapidly. After several disputes, including O’Banion’s sabotage of Sieben’s Brewery that cost Torrio approximately $7 million in today’s money, Torrio ordered a hit on O’Banion.

On November 10, 1924, three men entered Schofield’s Flower Shop. One offered his hand to O’Banion in what locals call a “Chicago Handshake” – grabbing and holding O’Banion’s right hand so he couldn’t reach for his gun. O’Banion was shot twice in the chest, twice in the throat, and once in the head. His funeral featured an astounding 26 truckloads of flowers.

After O’Banion’s death, Hymie Weiss took over the North Side Gang. Known for his intense, scary presence, Weiss was reportedly the only man Al Capone feared. On October 11, 1926, Weiss and his entourage were crossing the street near the cathedral when gunmen raked them with Thompson submachine gun fire from a second-floor apartment. Weiss took 10 bullets and died that day. Some stray rounds struck the church, and locals claim that one bullet hole can still be seen in the cornerstone.

Walking Directions to Stop 3: Continue south on State Street to East Ontario Street, then turn east. Walk to 55 E. Ontario St.

Stop 3: 21c Museum Hotel (formerly James Hotel)

Location: 55 E. Ontario St.

The James Hotel, formerly the Hotel McCormick, plays a significant role in Chicago gangster lore. This location is associated with “Machine Gun” Jack McGurn, one of Al Capone’s most trusted killers.

Born as Vincenzo Antonio Gibaldi in Sicily in 1902, McGurn immigrated to America at age 4 and eventually settled on Chicago’s West Side. A talented boxer who changed his name to sound more Irish (as Irish boxers were considered the toughest), McGurn caught the attention of the Capone organization after killing those responsible for his stepfather’s murder.

On March 7, 1928, McGurn and real estate man Nick Mastro were in the Hotel McCormick’s tobacco shop when members of the North Side Gang, who controlled this territory, decided to send McGurn a message. Two men burst into the shop with a pistol and a Thompson submachine gun. McGurn was wounded in the chest and arm but managed to escape to his room, where a hotel doctor treated him before he was taken to the hospital.

McGurn survived but refused to identify his attackers to police, saying he would “take care of it himself.” Witnesses identified the gunmen as Frank and Peter Gusenberg, hitmen from the North Side Gang. Both Gusenberg brothers were later killed in the infamous St. Valentine’s Day Massacre of 1929, which many believe McGurn helped orchestrate for Capone. McGurn himself was eventually murdered in a bowling alley on Milwaukee Avenue in 1936.

Walking Directions to Stop 4: Walk west back to State Street, then south to the corner of Grand Avenue and State Street.

Stop 4: Grand and State (Juice Loan Corner)

Location: Southeast corner of Grand Avenue and State Street

After Prohibition ended in 1933, Chicago mobsters diversified their criminal enterprises. One lucrative business was “juice loans” – illegal, high-interest loans that were common until a few decades ago. When banks were less accessible and credit cards weren’t widespread, the Chicago Outfit provided quick cash with no questions asked – but at an enormous price, with interest rates reaching 20% per week.

This intersection was where Frank and Nick Calabrese, two brothers from Chicago’s West Side, sold newspapers as children. As adults, they became top juice-loan racketeers for the Chicago Outfit, making millions for their bosses. This trust led them to become mob enforcers involved in at least 14 Outfit murders between 1970 and 1986.

The Calabrese brothers’ story took a dramatic turn decades later. While serving prison terms for loan-sharking, Frank Jr. (Frank’s son) approached the FBI wanting to keep his father locked up forever. Frank Jr. wore a wire to record his father discussing crimes, and Nick Calabrese eventually cooperated with the FBI in their investigation of old Outfit murders. This led to “Operation Family Secrets,” a landmark trial in 2007 that resulted in life sentences for several mobsters, including Frank Calabrese Sr., who died in prison on Christmas Day 2012. Nick Calabrese received a reduced sentence for his cooperation and entered witness protection upon release in 2013.

Walking Directions to Stop 5: Continue south on State Street to Wacker Drive. Turn west and stop in front of Marina Towers.

Stop 5: Marina Towers

Location: 290 N. State St (north side of Wacker Drive)

The distinctive Marina City towers, built in 1964, housed a fascinating character in Chicago organized crime history – Murray Humphreys, known as “The Camel.” Born to Welsh immigrants, Humphreys was a non-Italian associate of Al Capone who became a crucial part of the Chicago Outfit.

Humphreys started as a restaurant cook who was caught hijacking Capone’s bootleg liquor. Rather than punishing him, Capone was impressed and gave him a job. Humphreys eventually became the Outfit’s financial advisor, handling money transfers to politicians and other officials.

At the end of his life, Humphreys lived on the 51st floor of the east Marina City tower. The FBI had hidden microphones in his apartment to monitor conversations. In November 1965, FBI agents came to arrest him for dodging a subpoena. They had to wrestle the aging Humphreys to handcuff him. Although they didn’t lock him up that night, Humphreys was found dead of a heart attack hours later, likely from the stress of the confrontation.

Many believe that Murray Humphreys was the inspiration for the character Tom Hagen (played by Robert Duvall) in “The Godfather.”

Walking Directions to Stop 6: Continue west on Wacker Drive to the Clark Street Bridge.

Stop 6: Clark Street Bridge

Location: Clark Street Bridge over Chicago River

Built in 1929, the Clark Street Bridge offers excellent views of the Chicago River and downtown. It’s also connected to Vincent “Schemer” Drucci, who took over the North Side bootlegging gang after Hymie Weiss was killed in 1926.

Born in Chicago to Sicilian parents in 1898, Drucci served in the U.S. Navy during World War I before turning to crime. He got his nickname “The Schemer” from his wild ideas, like overthrowing the government to become president or stealing England’s crown jewels. Despite his prankster reputation (he once dressed as a priest to make inappropriate comments to passersby), Drucci had a violent temper that earned him enemies.

On April 4, 1927, police arrested Drucci for attempting to ransack a political opponent’s office during a mayoral election. While being transported from the police station to the Criminal Courts building, Drucci began threatening Sergeant Dan Healy, the arresting officer. When Drucci lunged at Healy and tried to grab his gun, Healy shot Drucci in the arm, leg, and abdomen. Drucci died later that day, becoming the only Chicago mob leader killed by law enforcement.

Some believe Drucci’s unpredictable and manic personality inspired the character of the Joker in Batman comics.

Walking Directions to Stop 7: Continue south on Clark Street, then turn east on Adams Street. Walk to Dearborn Street and turn south. Continue to Federal Plaza at Jackson and Dearborn.

Stop 7: Federal Plaza

Location: Jackson and Dearborn Street

Your final stop is Federal Plaza, home to the Kluczynski Federal Building, Post Office, and Dirksen United States Courthouse. This site represents law and order in Chicago’s gangland saga.

Before this complex was built, this was the location of the old Chicago Federal Building until 1965. The building hosted Al Capone’s famous 1931 tax evasion trial that resulted in his 11-year prison sentence. Though Capone had evaded prosecution for bootlegging and murder, the IRS eventually built a case against him for tax evasion following a 1927 Supreme Court ruling that illegally earned income was still taxable. Capone served time in Atlanta Federal Penitentiary and later Alcatraz before being released in 1939 due to declining health. He died in 1947 from complications of syphilis.

The modern Dirksen United States Courthouse hosted the landmark “Operation Family Secrets” trial in 2007, which dealt a significant blow to the Chicago Outfit. The case began when Frank Calabrese Jr. and his uncle Nick Calabrese (whom you learned about at Stop 4) cooperated with the FBI. The trial resulted in convictions for 18 gangland murders and life sentences for major Outfit figures, including Frank Calabrese Sr.

This operation marked the first time an official member of the Chicago Outfit (Nick Calabrese) testified against his former associates. While the trial significantly disrupted the Outfit’s operations, it didn’t eliminate the organization entirely. Both Frank Calabrese Jr. and Nick Calabrese still cannot return to Chicago for fear of retribution.

Conclusion

Congratulations on completing the Chicago Crime & Gangster Self-Guided Walking Tour! You’ve walked in the footsteps of some of America’s most notorious criminals and witnessed firsthand the locations where Chicago’s dark history unfolded.

If you enjoyed this self-guided experience and want to learn even more about Chicago’s fascinating criminal past, consider joining our expert-guided Chicago Crime and Gangster Tour. Our knowledgeable guides provide additional stories, insights, and historical context that bring these locations to life in even greater detail.

For more information or to book a guided tour, visit Free Chicago Walking Tours.

Map of Tour Route

Google Maps: Crime & Gangster Tour Route
Start Point: Old Water Tower/Jane Byrne Plaza (Michigan and Chicago Ave)
End Point: Federal Plaza (Jackson and Dearborn St)

Note: This self-guided tour is designed for informational and educational purposes only. Please be aware of your surroundings at all times and respect private property. Some historical sites may be located in busy areas; please use crosswalks and follow traffic signals for your safety.

Chicago – a city known worldwide for its stunning architecture, deep-dish pizza, and vibrant culture. But beneath its gleaming skyscrapers and beautiful lakefront lies a captivating darker history that has fascinated generations: its notorious legacy of crime and gangsters. From the early days of frontier lawlessness to the infamous Prohibition era and beyond, Chicago’s underworld has shaped not just the city’s identity but American popular culture as a whole.

Join us as we journey through the shadowy streets and hidden haunts of Chicago’s most infamous characters and discover why this captivating history continues to intrigue visitors from around the world.

The Seeds of Lawlessness: Chicago’s Early Criminal Days

Chicago’s reputation for lawlessness wasn’t born during Prohibition – it stretches back to the city’s earliest days. As early as the 1840s, while Chicago was transforming from a frontier outpost to a booming metropolis, it was already earning a dubious reputation for horse theft, robberies, and various criminal enterprises.

The city’s strategic location made it a hub for commerce, and where commerce thrived, so did illicit activities. By the mid-19th century, Chicago reportedly hosted more gambling establishments than Philadelphia (a larger city at the time) and had a higher per-capita concentration of gambling venues than New York.

The Great Chicago Fire of 1871 marked a turning point, not just in the city’s architectural development but also in its criminal landscape. The chaotic aftermath of the fire, with widespread looting and a breakdown in social order, created fertile ground for criminal activities to flourish.

Experience History Firsthand: On our Chicago Crime and Gangster Tour, you’ll walk through the very streets where Chicago’s criminal saga began. Our expert guides will bring these forgotten stories to life against the backdrop of Chicago’s historic landmarks.

 

The Birth of Chicago’s Underworld Legends

The late 19th and early 20th centuries saw Chicago’s criminal enterprises becoming more organized and its criminals more colorful. One such character was Michael “Mickey” Finn, owner of the Lone Star Saloon. In 1903, Finn was discovered to have been drugging his patrons’ drinks for years, allowing his staff to rob them while unconscious. His nefarious practice gave birth to the term “Mickey Finn” or “slipping a Mickey” – terminology that persists in our cultural lexicon more than a century later.

This period also saw the rise of powerful street gangs, such as Ragen’s Colts, an Irish gang whose influence extended beyond mere criminal activities and into Chicago’s social and political landscape. The gang’s involvement in the Chicago Race Riot of 1919 – which erupted after a Black teenager drowned in Lake Michigan and a white man was arrested for throwing rocks at Black swimmers – demonstrated how deeply criminal organizations had embedded themselves into the city’s fabric. The ensuing violence lasted for days, resulting in numerous deaths, injuries, and extensive property damage.

The Golden Age of Gangsters: Prohibition and the Rise of Organized Crime

While Chicago’s criminal history runs deep, it was the Prohibition era (1920-1933) that truly cemented the city’s reputation as America’s gangster capital. The nationwide ban on alcohol created an unprecedented opportunity for organized crime to flourish, and Chicago’s gangsters seized it with both hands.

Under figures like Johnny Torrio and later Al Capone, the Chicago Outfit transformed from a neighborhood gang into a sophisticated criminal empire that controlled a vast network of speakeasies, gambling dens, and brothels. The enormous profits from bootlegging allowed these organizations to expand their influence, bribing police officers, judges, and politicians to turn a blind eye to their activities.

Walk in Capone’s Footsteps: Our Chicago Crime and Gangster Tour guides you through the neighborhoods where the infamous “Beer Wars” between rival gangs played out, with stops at Holy Name Cathedral where you can still see evidence of a gangland shooting, and past sites where notorious figures like Dean O’Banion and Hymie Weiss conducted their deadly business.

 

The Key Players: Faces of Chicago’s Underworld

Al “Scarface” Capone

No discussion of Chicago’s criminal history would be complete without substantial mention of Alphonse Gabriel Capone. Rising from humble beginnings as a Brooklyn street thug to become the most notorious gangster in American history, Capone’s seven-year reign over Chicago’s underworld has become the stuff of legend.

What made Capone unique wasn’t just his willingness to use violence – though the brutal St. Valentine’s Day Massacre of 1929, where seven members of the rival North Side Gang were gunned down, certainly demonstrated that willingness. It was also his understanding of public relations. Despite his criminal activities, Capone carefully cultivated an image as a benevolent community figure, opening soup kitchens during the Great Depression and presenting himself as a businessman providing services the public demanded.

This carefully managed public persona helped Capone maintain popular support even as law enforcement intensified their efforts to bring him down. Ultimately, it wasn’t murder or bootlegging charges that ended Capone’s career, but tax evasion – a fact that highlights the complex relationship between Chicago’s gangsters and the law.

John Dillinger: Public Enemy Number One

Though not a Chicago native, bank robber John Dillinger’s dramatic final chapter played out on the city’s streets, forever linking him to Chicago’s gangster lore. Known for his daring bank robberies and prison escapes, Dillinger captured the public imagination during the depths of the Great Depression, with some seeing him as a folk hero striking back against the financial institutions many blamed for their economic suffering.

Dillinger’s story came to its dramatic conclusion outside the Biograph Theater in Chicago in 1934, where he was gunned down by FBI agents after being betrayed by the “Lady in Red,” Anna Sage. The theater and the alley where Dillinger fell remain popular stops for those interested in Chicago’s criminal history.

Stand Where History Happened: While our Chicago Crime and Gangster Tour focuses primarily on the North Side and Loop areas, our knowledgeable guides will share fascinating stories about Dillinger and other notorious figures who made their mark on the city’s criminal landscape. You’ll hear tales of “Machine Gun” Jack McGurn at the James Hotel and learn about the Chicago handshake – a deadly greeting in the gangster world.

 

The Supporting Cast

Chicago’s gangland drama featured a colorful cast of characters beyond just Capone and Dillinger:

• Vincenzo “Big Jim” Colosimo: Considered Chicago’s first “Vice Lord,” Colosimo established the South Side Gang that would later evolve into the Chicago Outfit under Torrio and Capone.
• Johnny “The Fox” Torrio: Colosimo’s successor and Capone’s mentor, Torrio was a strategic thinker who laid the groundwork for modern organized crime in America before passing the reins to Capone.
• Frank “The Enforcer” Nitti: Taking over after Capone’s imprisonment, Nitti expanded the Outfit’s operations into labor racketeering and extortion, ensuring the organization’s continued prosperity after Prohibition.
• George “Bugs” Moran: Leader of the North Side Gang and Capone’s chief rival, Moran was the intended target of the St. Valentine’s Day Massacre but arrived late, narrowly escaping death.

The Stage: Infamous Locations in Chicago’s Crime Saga

Chicago’s landscape is dotted with locations that played significant roles in its criminal history, many of which still stand today:

The Biograph Theater

This historic movie house in the Lincoln Park neighborhood remains perhaps the most famous site in Chicago’s gangster geography. It was here, on July 22, 1934, that John Dillinger attended a showing of the film “Manhattan Melodrama” before being gunned down by federal agents in a nearby alley. Today, the theater operates as a live performance venue, but its iconic marquee and façade remain largely unchanged from that fateful night.

St. Valentine’s Day Massacre Site

Though the original building at 2122 North Clark Street has long since been demolished (replaced by a parking lot for a nursing home), this site in Lincoln Park marks one of the bloodiest episodes in gangland history. On February 14, 1929, seven members of George “Bugs” Moran’s North Side Gang were lined up against a wall and executed by men posing as police officers, presumed to be working for Al Capone. The massacre shocked the nation and brought unprecedented law enforcement attention to Capone’s operations.

Holy Name Cathedral

This magnificent cathedral on State Street bears a unique connection to Chicago’s gangland wars – a bullet hole in its cornerstone from a 1926 shootout that killed Hymie Weiss, a member of the North Side Gang. This physical scar on one of the city’s most important religious buildings serves as a permanent reminder of how completely the violence of the gangster era permeated Chicago society.

Green Mill Cocktail Lounge

This Uptown jazz club, opened in 1907, was a favorite hangout of Al Capone, who had a regular table with a clear view of both entrances. The Green Mill also had a series of underground tunnels, allowing for quick escapes during police raids. Today, the Green Mill remains a popular jazz venue with much of its Prohibition-era ambiance preserved, offering visitors a chance to sip cocktails in the same space once frequented by Chicago’s most notorious gangster.

Experience Authentic Locations: The Chicago Crime and Gangster Tour brings you to many historic sites, including the Marina Towers where “The Camel” Murray Humphreys once lived, and locations associated with the notorious Calabrese brothers. You’ll stand at the Clark Street Bridge where Vincent “Schemer” Drucci met his end, and visit the Federal Plaza where some of Chicago’s most significant mob trials took place.

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Speakeasies: The Social Centers of Prohibition Chicago

The Prohibition era gave rise to one of Chicago’s most enduring cultural institutions: the speakeasy. These illicit drinking establishments, often hidden behind false fronts or requiring passwords for entry, became important social spaces during the dry years. Unlike the saloons they replaced, speakeasies often welcomed women as patrons, creating more integrated social scenes and challenging traditional gender norms.

Some notable Chicago speakeasies included:

• The Green Mill: Beyond being a Capone hangout, this venue was a premier jazz destination.
• Twin Anchors: Operating under the name “Tante Lee Soft Drinks” during Prohibition, this Old Town establishment claims to be one of Chicago’s oldest bars.
• The Drifter: Located beneath the Green Door Tavern, this modern speakeasy pays homage to its Prohibition-era roots.

Many of these establishments survived the end of Prohibition and continue to operate today, offering visitors a tangible connection to Chicago’s past. The legacy of speakeasies can also be seen in Chicago’s modern craft cocktail culture, which often draws inspiration from Prohibition-era mixology.

Cultural Impact: How Gangsters Shaped Chicago’s Identity

The impact of crime and gangsters on Chicago extends far beyond the historical events themselves. This era profoundly influenced Chicago’s culture in numerous ways:

Music and Entertainment

Chicago’s speakeasies became crucial incubators for jazz music, with musicians like Louis Armstrong and King Oliver finding receptive audiences in these underground venues. The association between jazz and the criminal underworld created a sense of danger and rebellion that helped propel the genre to national prominence.

Literature and Film

Chicago’s crime history has inspired countless works of literature and film, from contemporaneous novels like James T. Farrell’s “Studs Lonigan” trilogy to later works like Nelson Algren’s “The Man with the Golden Arm.” In cinema, gangster films became a distinct genre, with movies like “Scarface” (1932), “The Untouchables” (1987), and “Road to Perdition” (2002) all drawing inspiration from Chicago’s criminal past.

Architecture and Urban Development

The enormous profits generated by bootlegging and other illicit activities during Prohibition found their way into legitimate investments, including some of Chicago’s iconic buildings. The Carbide & Carbon Building, with its dark green and gold façade resembling a champagne bottle, is just one example of how Prohibition-era wealth shaped the city’s skyline.

The Legacy: Chicago’s Ongoing Relationship with its Criminal Past

While the era of Al Capone and the Chicago Outfit’s dominance has long passed, the city continues to grapple with this complex legacy. Today’s Chicago presents two faces to visitors interested in its gangster history: the romanticized version found in tours and museums, and the more sobering reality of how organized crime impacted communities and continues to influence perceptions of the city.

Modern organized crime in Chicago looks very different from its Prohibition-era counterpart, but echoes of that history occasionally resurface in news headlines. Recent developments, like the February 2024 delayed sentencing of reputed mobster Paul Carparelli and the March 2025 judicial decision regarding bribery convictions in the ComEd 4 case, demonstrate that Chicago’s relationship with corruption and organized crime remains an ongoing story.

Experience Chicago’s Gangster History Firsthand

Reading about Chicago’s fascinating criminal history is one thing, but walking the actual streets where these events unfolded creates a connection to the past that no book or film can match. Our Chicago Crime and Gangster Tour offers precisely this immersive experience.

Led by expert guides with deep knowledge of Chicago’s history, our tour takes you to the actual locations where gangland history was made:

• Visit Holy Name Cathedral and see evidence of gangland violence, including the site where Dean O’Banion and Hymie Weiss operated
• Stand at the James Hotel where “Machine Gun” Jack McGurn narrowly escaped death
• Learn about the notorious “juice loan” operations run by the Calabrese brothers
• Visit the Marina Towers where Murray “The Camel” Humphreys, a close associate of Al Capone, spent his final days
• Stand at the Clark Street Bridge where “Schemer” Drucci was killed
• Explore the site where Tony Accardo ran his illegal gambling operations
• Finish at Federal Plaza, where both Al Capone and modern mobsters faced justice

Whether you’re a history buff, a true crime enthusiast, or simply curious about Chicago’s colorful past, our tour offers insights and stories you won’t find in guidebooks. Our knowledgeable guides bring these historical events to life, placing them in the broader context of Chicago’s development while separating fact from the many myths surrounding these infamous figures.

Conclusion: Why Chicago’s Gangster History Still Captivates

Chicago’s crime and gangster history continues to fascinate because it represents more than just a collection of colorful characters and violent events. It tells a larger American story about immigration, social mobility, prohibition, and the urban experience. The gangsters of Chicago, with their custom suits and tommy guns, have become cultural archetypes that continue to influence how we think about crime, wealth, and power.

Whether experienced through books, films, or walking tours, Chicago’s gangster history offers a window into a transformative period in American urban life. As you walk Chicago’s streets today, among its gleaming skyscrapers and bustling neighborhoods, remember that you’re treading the same ground once walked by some of history’s most notorious figures – characters whose legacy continues to shape the city’s identity over a century later.

Ready to step back in time and experience Chicago’s gangster era firsthand? Book your spot on our Chicago Crime and Gangster Tour today. Our tour takes you on a fascinating journey through the dark side of Chicago that’s easy to overlook but impossible to forget. Join our expert guides as they peel back the curtain on Chicago’s criminal past and discover the fascinating stories behind the Windy City’s most notorious chapter.

This self-guided tour is perfect for guests that cannot join a scheduled Chicago Holiday Walking Tour.

Welcome to our self-guided Chicago Holiday Walking Tour! Experience the magic of the holiday season in the heart of the Windy City. This tour will take you through some of Chicago’s most iconic landmarks, all dressed up in their festive best. Along the way, you’ll discover rich histories, enchanting decorations, and heartwarming stories that embody the spirit of the holidays in Chicago.

Stop 1: Millennium Park Christmas Tree and Ice Skating Rink

201 E Randolph St, Chicago, IL 60602

What to See

• Chicago’s Official Christmas Tree: Admire the towering Christmas tree adorned with thousands of twinkling lights and ornaments.
• McCormick Tribune Ice Rink: Watch skaters glide under the city skyline or rent skates yourself for a memorable experience.
• Cloud Gate (“The Bean”): Don’t miss this iconic sculpture reflecting the festive surroundings.

Points of Interest

• Photo Opportunities: Capture the festive atmosphere with the illuminated tree and skyline as your backdrop.
• Holiday Music: Enjoy seasonal tunes often played around the rink and tree area.

Stories to Share

• Chicago’s Christmas Tree Tradition: In 1913, Chicago lit its first municipal Christmas tree, a 35-foot Douglas spruce, in Grant Park. Mayor Carter Harrison Jr. dedicated it as a symbol of hope and unity.
• Transformation of Millennium Park: Once a desolate rail yard, the park opened in 2004 and has become a central hub for Chicago’s cultural and holiday festivities.
• “The Bean” in Winter: Designed by Anish Kapoor, the Cloud Gate sculpture offers a unique view during the holidays, reflecting the lights and snow, creating a magical visual effect.

Stop 2: Chicago Cultural Center

Address: 78 E Washington St, Chicago, IL 60602

What to See

• Preston Bradley Hall: Marvel at the world’s largest Tiffany stained-glass dome, measuring 38 feet in diameter.
• Rotunda and Grand Staircase: Observe the intricate mosaics and marble detailing.
• Holiday Exhibits: Check for seasonal art installations and free concerts.

Points of Interest

• Warm Indoor Space: Take a break from the cold while enjoying the opulent interior.
• Information Desk: Pick up brochures about current exhibits and events.

Stories to Share

• A Palace for the People: Opened in 1897 as Chicago’s first public library, the building symbolized the city’s commitment to accessibility and education.
• Architectural Marvel: The Beaux-Arts building was designed by Shepley, Rutan, and Coolidge, showcasing lavish materials and craftsmanship meant to inspire visitors.
• Cultural Hub: Since 1991, it has served as the Chicago Cultural Center, hosting over 1,000 programs annually, all free to the public.

Stop 3: Macy’s on State Street (Formerly Marshall Field’s)

Address: 111 N State St, Chicago, IL 60602

What to See

• Holiday Window Displays: Stroll along State Street to view the elaborate, themed displays enchanting visitors since the early 1870s.
• The Walnut Room: Located on the 7th floor, it’s home to the Great Tree, a two-story Christmas tree decorated with hundreds of ornaments.
• Tiffany Ceiling: Inside the store, look up to see the largest unbroken example of Tiffany Favrile glass in the world.

Points of Interest

• Dining Experience: Consider making a reservation at The Walnut Room to dine next to the Great Tree.
• Shopping and Souvenirs: Explore unique gifts and holiday specials throughout the store.

Stories to Share

• Marshall Field’s Legacy: Established in 1852, the store became a retail pioneer, introducing concepts like the bridal registry and in-store dining.
• Holiday Windows Tradition: The animated window displays began in the early 20th century, delighting generations with stories like “A Christmas Carol” and “The Nutcracker.”
• The Great Tree: Since 1907, the Walnut Room has featured a grand Christmas tree, becoming a cherished Chicago tradition.
• Transition to Macy’s: In 2006, Marshall Field’s was rebranded as Macy’s, sparking local debate but continuing the store’s holiday customs.

Stop 4: The Palmer House, A Hilton Hotel

Address: 17 E Monroe St, Chicago, IL 60603

What to See

• Grand Lobby: Admire the French Baroque-style ceiling frescoes, chandeliers, and the majestic “Winged Angels” on the grand staircase.
• Historical Displays: Find exhibits showcasing the hotel’s rich history and famous guests.
• Lockwood Bar and Restaurant: A cozy spot to warm up with a drink or snack.

Points of Interest

• Art and Architecture: Pay attention to the intricate designs by architect John M. Van Osdel.
• Palmer House Brownies: Try the original brownie recipe created here.

Stories to Share

• A Love Story Built in Stone: Potter Palmer built the original hotel as a wedding gift for his wife, Bertha Honore Palmer. After it burned down in the Great Chicago Fire of 1871, he rebuilt it grander than before.
• Innovation and Luxury: The rebuilt Palmer House was the nation’s first fireproof hotel and featured modern amenities like electric light bulbs, telephones, and elevators.
• Invention of the Brownie: In 1893, Bertha Palmer requested a portable dessert for ladies attending the World’s Columbian Exposition, leading to the creation of the chocolate fudge brownie.
• Famous Guests: The hotel has hosted luminaries like Charles Dickens, Oscar Wilde, Judy Garland, and every U.S. president since Ulysses S. Grant.

Stop 5: Christkindlmarket Chicago at Daley Plaza

Address: 50 W Washington St, Chicago, IL 60602

What to See

• Festive Market Booths: Explore over 50 vendors selling handmade ornaments, nutcrackers, cuckoo clocks, and other gifts.
• Culinary Delights: Enjoy German specialties like bratwurst, schnitzel, potato pancakes, and Glühwein (hot spiced wine) served in collectible mugs.
• Daley Plaza Christmas Tree: A beautifully decorated tree that serves as the market’s centerpiece.
• The Picasso Sculpture: An untitled 50-foot steel sculpture by Pablo Picasso.

Points of Interest

• Live Entertainment: Check the schedule for carolers, dance performances, and appearances by the Christkind.
• Souvenir Mugs: Each year features a new mug design—great keepsakes!

Stories to Share

• German Heritage in Chicago: In the 19th century, German immigrants were the largest ethnic group in Chicago, greatly influencing the city’s culture and traditions.
• Origin of Christkindlmarket: Established in 1996, it was inspired by the 16th-century Christkindlesmarkt in Nuremberg, Germany. It’s now the largest Christmas market in the U.S.
• The Christkind: A fairy-like being from German folklore who brings gifts to children. The market’s Christkind opens the event with a prologue.
• The Picasso Sculpture: Unveiled in 1967, it was initially met with mixed reactions but has since become a beloved landmark. Its abstract form adds a modern contrast to the traditional market.

Additional Tips

• Stay Warm: Between stops, consider warming up with a hot beverage from local cafes like Intelligentsia Coffee (53 E Randolph St) or Caffè Rom (200 S Michigan Ave).
• Accessibility: The route is wheelchair and stroller friendly.
• Plan Ahead: Check the operating hours of Christkindlmarket and The Walnut Room, especially if visiting on a holiday.

This festive tour showcases the heart and history of Chicago’s holiday celebrations. From glittering lights to timeless traditions, each stop offers a unique glimpse into what makes the season special in the Windy City. We hope this journey fills you with joy and creates lasting memories. Happy Holidays!

A big shout out and thank you to Nikola at Structure Photography (http://www.structurephotography.org) for braving the elements with one of our Free Chicago Walking Tours and sharing some incredible pictures he captured while visiting Chicago. He shows that even on a not-so-perfect-day you can still get your great shot.

About Structure Photography & Nikola Olic

Nikola Olic is a photographer living and working in Dallas, Texas, focusing on architectural photography and abstract structural quotes that reimagine their subjects in playful, dimensionless and disorienting ways. His photography has appeared in various galleries, art events, museums, magazines, newspapers, and websites around the world.

Without further ado, please enjoy the photos Nikola captured on his visit to Chicago along with the location and information about each shot.

8:01am – 899 W Harrison St / UIC School of Architecture. The early morning gray was opportunely countered by the colorful public display across the street from the UIC School of Architecture, offering a seemingly conflicted visual space of a colorful public display and a gray colorless city behind it.

8:21am – 50 Ida B. Wells Dr / Roosevelt University Another way to improve the weather — at least temporarily — is to replace the gray background with a blue one, even if it belongs to a modern building and its glass facade.

9:02am – Prudential Plaza + Buckingham Fountain This photographs represents 3 rather than just one location. It was taken from Shedd Aquarium, and it depicts the water fountain of the Buckingham Fountain, decorating the uniform facade of the Prudential Plaza a few blocks behind.

9:41am – Jay Pritzker Pavilion The pavilion has ample opportunities for photography, with such a diversity of Chicago architectural options and styles offered around it. In this case, the overhead structures that help bring sound and lights closer to the audience also help frame a building near by.

10:00am – Shedd Aquarium Back to the Aquarium for more photographs, in this case lightly quoting famed Italian photographer Luigi Ghirri and his vertical dividing beams, used to frame distant water activity.

10:32am – Prudential Plaza The public space in front of the building offers a performance space and a Colosseum-like structure that can also be used to help frame and isolate interesting architectural details nearby.

11:16am – 432 W Lake St / Fulton River District From a particularly extended spot in the walking area in front one of the buildings facing the river, surrounding buildings come together in an unexpected visual space that combines and breaks and bends visual lines in dimensionless and disorienting ways.

11:33am – 432 W Lake St A small convenience store offers a unique and different view of the famed Marina City buildings, instantly recognizable to Chicago residents, even when reflected in a window which almost morphs the buildings into something else.

12:14am – Waterview Tower Another unique view of the famed Marina City buildings, this time reflected in an even less recognizable fashion, of the facade of the Waterview Tower.

1:47pm – The Bean / Cloud Gate One of the most recognizable visuals in Chicago, the Cloud Gate sculpture in Millennium Park (aka The Bean) helps a bird rest, while also providing cover for a building behind it.

2:52pm – Sofitel Hotel The striking building of the Sofitel hotel provides a sharp angle that can be used as a central figure in a photograph that balances the hotel and its facade with the empty Chicago sky, offering a quick break from the saturated architectural visual space of this fascinating city.

3:06pm – John Hancock Center The world-famous John Hancock Center has an interesting addition on its west side: a garage with a spiral driveway visible from the outside.

3:21pm – 840 N Michigan Ave The non-descript building near John Hancock center offers another view of the famous building, contrasting Hancock’s cross beams with this building’s horizontal facade sections.

4:11pm – 120e E Walton St Different sections of the building offer a unique opening towards the sky, and a unique light-shaped space that breaks the shadow in the early afternoon hours.

5:00pm – 1100ish N State St I had to “-ish” the address because I cant find it on Google Maps; Not the first time this happened with the dynamic city such as Chicago. The building offers a Picasso-like cubist reflection of — and reflection on — the famed Hancock tower a few blocks east from here.

5:21pm – 505 N St Clair St Eating pizza nearby, the similarly colored buildings a few blocks behind combine their similar facades and their sun reflections and reflections of each other, to provide an entertaining visual space.

6:11pm – 899 W Harrison St / UIC School of Architecture Back to the place where the walk started 10 hours ago, the improved light conditions provided new opportunities with the colorful public display, now worthy of its dedicated own photographic space.

This post contains affiliate links and I will be compensated if you make a purchase after clicking on my links.

With summer finally arriving in Chicago it’s about time to talk about all that the city has to offer. One of our favorite ways to experience attractions in Chicago AND save some money is by purchasing a Chicago Explorer Pass from Smart Destinations.

The Chicago Explorer Pass allows you to purchase admission to 3, 4 or 5 different attractions in Chicago for a discounted price. Below are our top 3 attractions. (Note: You can select from 28 different ones, so even if there isn’t something you like below make sure to check out all they have to offer.)

The 3-attractions Chicago Explorer Pass will cost $79/adult. The 3 destinations that we selected below would cost $114.92 at the gate for a total savings of $35.92 or 31%! If 3 attractions is not enough there are 4 attraction, 5 attraction and unlimited options as well.

Hop on, Hop off Big Bus Chicago 1-Day classic tour

Gate Price: $45.00

We’re guessing that after a 2-hour Free Chicago Walking Tour you’ll want to kick back and relax and there isn’t a better way to do than on the Big Bus Chicago 1-Day Class Tour with live guides, a comprehensive route that takes you through the best Chicago sites & gives you a chance to hop on and off at your leisure.

shoreline architecture river cruise

Gate Price: $45.92

We’ve said a million times (ok, not really). There is nothing better than being on a boat cruising the Chicago River. The sun. The beer. The gorgeous architecture. The incredible live guides.

Honestly, every guide for Free Chicago Walking Tours takes a Chicago River Architecture cruise each year. And most times we’re bringing our families along too. Every single year!

As a guest aboard the Shoreline Architecture River Cruise you will sail all 3 branches of the Chicago River: Main Branch, North Brand & South Branch. Heads up that this tour is CLOSED from November to April.

skydeck chicago

Gate Price: $24.00

Skydeck Chicago is perched some 1,353 feet above the streets of Chicago in The Willis Tower (formerly Sears Tower). From up there you can see parts of 4 different states and take a step out onto “The Ledge” which is a glass balcony that extends past the side of the building. Fair waring it is nerve-racking.

Make sure to bring your camera and if you’re able to try and go early on a weekday as the weekends can get really busy and sometimes the wait is more than an hour to get up there.

One of the greatest things about Chicago is the nightlife~ Chicago is full of great clubs, bars, and after hour eating establishments. Now that the weather is getting warmer, it’s time to switch from indoor bars to exciting outdoor rooftop bars! Rooftop bars in Chicago are great places to visit for many reasons; not only will you get to grab a drink in a cool establishment, but you can also grab a view of the Chicago skyline! Check out the list below and be sure to stop by one of these great locations.

The J. Parker

1816 N Clark St, Chicago, IL 60614

Source: The J. Parker

We put The J. Parker first on our list for a reason. Most of the popular rooftop bars are located in The Loop or River North, and we totally get it. They’re awesome. If however you’re looking for something a little different head north to Lincoln Park and to the 14th floor of the Lincoln Hotel and you’ll find yourself the beneficiary of panoramic views of Lincoln Park, the shores of Lake Michigan and a spectacular view of the Chicago skyline looking south.

My wife and I lived in Lincoln Park for a couple of years and grabbing a drink here in the summer never got old. Head to the Green City Farmers Market on Saturday morning and then cross the street to grab a cocktail and soak in the views. Now that’s a great start to the day!

Cindy’s Rooftop Restaurant

12 S Michigan Ave, Chicago, IL 60603

Source: Cindy’s Rooftop Bar

When people think rooftop bars in Chicago, they think of Cindy’s. Not only will this bar give you great views of Lake Michigan and Millennium Park, but you also get a five-star dining experience.

Cindy’s is open until 1am on weekdays, and 2am on weekends, making a great late night spot too for a nightcap drink or even a midnight meal. This bars rooftop is covered, so you can enjoy Cindy’s year round, even in the bitterly cold Chicago winters!

AIRE

100 W Monroe St, Chicago, IL 60603

Source: Hyatt Centric

AIRE is the hidden gem of rooftop bars. You will pay a bit of money to dine here, but remember, it’s about the atmosphere! There are very few rooftop bars in Chicago that offer the high end atmosphere that AIRE does. Make sure to plan your time here on a clear night, there is no awning covering the lounge area. If it’s a rainy or windy night, reschedule for another time. It will be worth it!

Drumbar

201 E Delaware Pl, Chicago, IL 60611

Source: Drumbar

Forbes magazine named Drumbar the best rooftop bar in Chicago, and they did so for a good reason. Drumbar was also named the “Best Whiskey Bar” by GQ Magazine. They have an incredible indoor lounge, as well as an outdoor terrace with downtown and speakeasy-style decor. Located at the top of the Raffaello hotel, this rooftop bar is a must-see for locals and tourists alike. With all cocktails being $16, you know exactly what you are going to pay. No hidden fees or upsells. Spots fill up fast, so be sure to fill out a reservation!

Raised

1 West Upper Wacker Drive, Chicago, IL 60601

Source: Raised Bar

Not only is Raised a great place to grab drinks, but they have an incredible menu. All of their menu items are made using ingredients sourced from within 200 miles of the restaurant. Sometimes, you want to grab a meal while you are at a bar, and this is the place to do it. The cool thing about this bar is that there are no reservations, making it a great choice for you and your friends when you just randomly decide that you want to attend a rooftop bar.

No matter which rooftop bar in Chicago you want to attend, going to either one of these locations means you will have a great night filled with memories!

Chicago doesn’t have a shortage of things to do. In fact, we’ve written about Chicago FREE Things to Do, non-free Chicago Things to do and the top paid tours in Chicago. Almost no matter what the number one question we receive is “what are the best non-touristy things to do?” Markets. Chicago Markets. And here are the best of the best.

These markets contain dozens of vendors all under one roof (or at least in the same vicinity if a roof doesn’t exist). It’s easy to explore new foods, new cultures, and check out all the best new “stuff” that is available. Instead of heading to an Italian restaurant, head on over to an Italian market where you can explore different restaurants and vendors, and even buy some food to take home with you!

Here is a list of the top four markets you MUST check out in the Chicago area.

Eataly

43 E Ohio St, Chicago, IL 60611

© 2013 Galdones Photography/Eataly

Ok, we admit it, this one is sort of touristy. But still, if you are looking for an authentic and eventful Italian marketplace, look no further than Mario Batali and Joe Bastianich’s Eataly Market. There are several different locations all over the world, but the Chicago location is actually the largest, spanning 65,000 square feet.

This marketplace is full of retail stores, restaurants, and ‘street sellers’ selling different authentic foods just like a real Italian marketplace. Not only will you get to buy delicious foods and wine, but you will also get an incredible experience.

They have a Nutella bar. You can walk around with a beer or glass of wine in your hand. Do you need more reasons to go?

French Market in Ogilvie Transportation Center

131 N Clinton St, Chicago, IL 60661

From Italy to France. The French Market in Ogilvie is an indoor, year-round, farmers market full of amazing foods, gifts, and other merchandise. The French Market brings in some of the best vendors that Chicago has to offer from all sorts of different neighborhoods. This marketplace contains smaller vendors who are entrepreneurs and families who own their own businesses. Not only are you getting some great stuff, but you are also supporting local small businesses in Chicago.This market’s vendors sell cheeses, meats, wine, seafood, and even ice cream.

Lincoln Park Farmers Market

1817 N Clark St, Chicago, IL 60614

The Lincoln Park Farmers Market is one of the most popular farmer’s markets in the Chicago area. This farmers market is a one-stop shop to get all of your in-season produce fresh from the farms themselves. Farmers from all over come to the Lincoln Park Farmers Market every Saturday morning to showcase their goods. Imagine buying fresh apples from a farmer in Indiana, or amazing grapes from the infamous southwest Michigan vineyards! There are so many great options here. This farmers market is open every Saturday from 7 am to 1 pm from May-October.

Logan Square Farmers Market

2363 N Milwaukee Ave, Chicago, IL 60647

The Logan Square farmers market is a one-stop shop for organic foods, retail merchandise, and live music. This market is year round, but it moves outdoors every spring! You can come visit this market on Sundays from 10 am – 3 pm. With new vendors all the time, you can come by and find something unique!