Chicago Riverwalk & Mobsters: The Architecture of Crime and Titans
A walk through the birthplace of the skyscraper, Al Capone's speakeasies, and soaring Art Deco riverside canyons
Chicago · 7 stops · 10 min audio · Generated
-
1. Wrigley Building & DuSable Bridge: Gateway of the Magnificent Mile
400-410 N Michigan Ave, Chicago, IL 60611
Stand right here on the plaza paving at the northern abutment of the DuSable Bridge and gaze up at the gleaming, brilliant white towers of the Wrigley Building. Completed in nineteen twenty-four as the global headquarters of chewing-gum magnate William Wrigley Junior, this French Renaissance revival marvel was clad in over two hundred and fifty thousand glazed terra-cotta tiles that are still hand-washed with soapy water to keep their luminous shine.
Notice how the clock tower resembles the Giralda tower of Seville Cathedral. Look down at the bridge below your shoes: inaugurated in nineteen twenty, the DuSable Bridge was the world's first double-deck trunnion bascule bridge, connecting downtown Chicago to the Magnificent Mile. The four stone bridge tender houses feature colossal carved limestone reliefs depicting early French explorers and the bloody eighteen twelve Fort Dearborn Massacre, which occurred just yards from where you stand.
During Prohibition, the waters flowing below this bridge were the nocturnal highway of bootleg rum-running speedboats smuggling Canadian whiskey from Lake Michigan straight into Al Capone's subterranean river vaults.
Cross Michigan Avenue to the soaring Gothic buttresses of Tribune Tower.
-
2. Tribune Tower & The Embedded World Relics: The Gothic Giant
435 N Michigan Ave, Chicago, IL 60611
Walk right up to the heavy limestone exterior wall of Tribune Tower and run your fingers across the rough stones set into the facade. You are looking at an architectural museum of world history: eccentric newspaper publisher Colonel Robert McCormick instructed his foreign correspondents to bring back authentic stone fragments from the greatest monuments on Earth. Embedded right at eye level, you can touch fragments from the Great Pyramid of Giza, the Parthenon, the Taj Mahal, the Roman Colosseum, and even a rock from the Moon!
In nineteen twenty-two, the Chicago Tribune hosted the most famous international architectural competition of the twentieth century to design the most beautiful office building in the world. New York architects John Mead Howells and Raymond Hood won with this soaring neo-Gothic skyscraper, crowning its top with thirty-six-foot flying buttresses inspired by Rouen Cathedral in France.
McCormick was so paranoid during the gangster wars that he kept two loaded pistols in his desk drawers and rode through the streets in an armored limousine, fearing ambushes from Capone's North Side rivals.
Walk down the staircase to the Chicago Riverwalk below.
-
3. Chicago Riverwalk & Vietnam Veterans Memorial: The Reclaimed River
Chicago Riverwalk at State St, Chicago, IL 60601
Step down to the water's edge along the wide concrete promenade of the Chicago Riverwalk and listen to the gentle lap of the river against the timber fenders. You are walking along what city planners once called a foul open sewer, now transformed into one of the most breathtaking urban waterfronts in the world.
In nineteen hundred, Chicago performed one of the greatest civil engineering feats in human history: engineers permanently reversed the flow of the entire Chicago River! By constructing the sanitary canal, they made the river flow backward away from Lake Michigan toward the Mississippi River basin, protecting the city's drinking water from deadly typhoid and cholera epidemics.
Pause at the semicircular granite plaza of the Vietnam Veterans Memorial: inscribed with the names of nearly three thousand Illinois servicemen who lost their lives in Southeast Asia, the terraced waterfall provides a serene sanctuary amid the echoing city canyons.
Look across the river at the iconic twin circular towers of Marina City.
-
4. Marina City: The Corncob Towers of Bertrand Goldberg
300 N State St, Chicago, IL 60654
Look up across the river at the twin sixty-story cylindrical towers of Marina City, affectionately dubbed the Corncobs by generations of Chicagoans. Notice the remarkable design: the bottom nineteen floors are open spiral parking ramps where parked cars seem to dangle dramatically over the edge of the abyss, while the upper forty stories blossom into semicircular residential balconies.
Designed by visionary architect Bertrand Goldberg, a student of Ludwig Mies van der Rohe at the Bauhaus, Marina City was completed in nineteen sixty-four as a radical city within a city. At a time when suburban flight was draining American downtowns, Goldberg designed these towers with a bowling alley, ice-skating rink, theater, marina for seven hundred boats, and groceries so residents could live, work, and play twenty-four hours a day without ever leaving the property.
Movie lovers will remember the famous stunt in the nineteen eighty Steve McQueen film The Hunter, where a stunt driver raced a Pontiac off the sixteenth floor of the parking ramp, plunging straight into the Chicago River below!
Continue west along the riverwalk toward the colossal Merchandise Mart.
-
5. The Merchandise Mart: The Titan on the River
222 W Merchandise Mart Plaza, Chicago, IL 60654
Stand on the riverbank opposite the gargantuan limestone and terracotta facade of the Merchandise Mart. Stretching for two full city blocks with four million square feet of floor space, this colossal Art Deco monolith was the largest building in the world by floor area when Marshall Field and Company opened it in nineteen thirty, surpassed only by the Pentagon during World War Two.
The building is so massive that it was assigned its very own dedicated United States postal ZIP code: sixty-six-fifty-four. In nineteen forty-five, Joseph P. Kennedy, patriarch of the Kennedy political dynasty, purchased the entire building for a bargain twelve and a half million dollars, generating the enormous family fortune that financed John F. Kennedy's presidential campaign.
Look across the water at night: the facade becomes the canvas for Art on theMart, the largest permanent digital projection mapping installation on Earth, projecting moving contemporary art across two and a half acres of stone.
Head north into River North toward the bullet scars of Holy Name Cathedral.
-
6. Holy Name Cathedral & The Hymie Weiss Hit: Mobster Bullets in Stone
735 N State St, Chicago, IL 60654
Walk up to the corner of State and Superior Streets and examine the limestone cornerstone near the entrance steps of Holy Name Cathedral. Look closely at the carved lettering: you can see a distinct, chipped indentation in the stone. You are touching an authentic bullet scar from the violent zenith of the Chicago Beer Wars of nineteen twenty-six.
On October eleventh, nineteen twenty-six, Earl Hymie Weiss, leader of the North Side Gang and the only man Al Capone truly feared, was walking toward his headquarters right across the street alongside his bodyguard. Suddenly, two hitmen armed with a Tommy gun and a shotgun opened fire from second-story windows of a nearby brownstone. Over ten bullets struck Weiss, killing him instantly.
Stray machine-gun rounds tore into the sacred facade of Holy Name Cathedral, leaving this bullet mark that church officials have deliberately left unpatched for a century as a solemn reminder of the city's turbulent past.
Step inside the serene Gothic interior: hanging high in the ceiling vault are the red galero hats of Chicago's deceased cardinals. According to Catholic tradition, when the hats eventually rot and fall to the floor, the cardinal's soul is released from purgatory.
Walk east toward the historic watering holes of the Gold Coast.
-
7. The Biograph & Green Mill Legacy: Dillinger's Last Stand
Lincoln Ave & Michigan Ave Corridor, Chicago, IL 60614
Conclude your journey reflecting on Chicago's legendary criminal underworld along the historic entertainment corridor. Picture the hot summer night of July twenty-second, nineteen thirty-four, outside the Biograph Theater. Public Enemy Number One, bank robber John Dillinger, walked out of the cinema after watching the gangster film Manhattan Melodrama, accompanied by the mysterious Woman in Red, brothel madam Anna Sage, who had tipped off the FBI in exchange for avoiding deportation.
As Dillinger walked into the alley, FBI special agent Melvin Purvis lit a cigar—the prearranged signal. Federal agents closed in shouting Halt! Dillinger reached for his pistol in his trousers, but four bullets tore into his back and neck, dropping him into the bloodstained alley paving. Bystanders rushed forward, dipping handkerchiefs and newspapers into his blood for macabre souvenirs.
Across town at The Green Mill Lounge in Uptown, Al Capone had his own private booth reserved with trapdoors leading to tunnels beneath the street for rapid escape during police raids, where jazz clarinetist Johnny Dodds played through the night.
From the ashes of the Great Fire to the rise of architectural titans, Chicago turned adversity into unyielding strength: a city whose towering skyline touches the clouds.