Chicago – The Capital of Prohibition
When the 18th Amendment to the U.S. Constitution prohibited the production, sale, and transportation of alcohol on January 17, 1920, no other American city responded to this ban with such audacity as Chicago. Within a few years, the city had around 20,000 illegal establishments – three times more than the 7,000 legal saloons that were closed after Prohibition was enacted. Chicago became synonymous with organized crime, political corruption, and a cultural revolt against the federal ban.
It was here that Al Capone built an empire worth $120 million a year. Here, gangsters waged bloody wars for control over alcohol smuggling. And here – particularly significant for Polish readers – one of the most powerful mafia bosses was a Pole, Henryk Wojciechowski, known as Hymie Weiss, the only man whom Capone feared.
Today, Chicago is a city that has not forgotten its Prohibition past. Hidden bars in speakeasy style thrive in former basements and behind unmarked doors, while legendary establishments like the Green Mill have been operating continuously for over a hundred years. This guide will take you on a journey from the bloody twenties to the best contemporary hidden bars in the Windy City.
Chicago During Prohibition
Chicago was the ideal city for smugglers. Its location – on Lake Michigan, at the center of a railway network connecting the East with the West – made it a natural hub for distributing illegal alcohol. Whiskey flowed from Canada through the Great Lakes, beer was brewed in hundreds of secret breweries in basements and on farms outside the city, and the finished product was shipped by train throughout the Midwest.
Politics played a key role. Mayor William “Big Bill" Thompson, who ruled Chicago from 1915 to 1923 and again from 1927 to 1931, openly opposed enforcing Prohibition. During his 1927 election campaign, he promised to be “wetter than the Atlantic” – and he kept his word. Police in many districts were on the gangsters' payroll. Entire precincts turned a blind eye to illegal establishments in exchange for regular bribes.
The scale of the phenomenon was staggering. At the height of Prohibition, Chicago had more speakeasies per capita than New York. Alcohol could be purchased practically anywhere – in restaurants, pharmacies, barbershops, “soft drink” stores, and even in some police precincts. Federal agents, of whom there were only a few dozen for the entire city, stood no chance against an army of smugglers supported by corrupt politicians.
Fun Fact: In 1927, Chicago had only 200 federal agents responsible for enforcing Prohibition – for a city with over 3 million residents at the time. Statistically, one agent was responsible for 15,000 people.
Al Capone and the Whiskey Empire
Alphonse Gabriel Capone arrived in Chicago from Brooklyn in 1920, at the invitation of gangster Johnny Torrio. He was 21 years old and had a scar on his cheek that earned him the nickname “Scarface.” In just five years, he built the largest criminal empire in American history.
The Four Deuces – Headquarters
Capone's first operational base was the establishment The Four Deuces at 2222 South Wabash Avenue – an address made up of four twos that gave the entire establishment its name. The ground floor housed a bar, the first floor a gambling house, the second a brothel, and the third an office from which Capone managed his growing empire. The building has not survived to this day.
Lexington Hotel – The Gangster's Palace
As Capone's influence grew, his headquarters moved to the luxurious Lexington Hotel on Michigan Avenue. Capone occupied several floors, protected by armed men. The hotel served as the command center for operations worth – according to FBI estimates – $120 million a year (in today's value, nearly $2 billion). This amount included income from smuggling and selling alcohol, gambling, prostitution, and extortion.
Organization
Capone's empire employed thousands of people – from smugglers and drivers to bartenders and waiters in speakeasies, as well as corrupt police officers and politicians. Capone controlled beer production in dozens of secret breweries, whiskey imports from Canada, and distribution to thousands of establishments throughout the city. His men operated in over 160 neighborhoods in Chicago.
Paradoxically, Capone enjoyed considerable public sympathy. During the Great Depression, he opened one of the first free soup kitchens in Chicago, feeding thousands of unemployed people. Many residents saw him as a Robin Hood – a man who provided people with what they wanted (alcohol) and helped those in need while the government prohibited and did not help.
The end came not from bullets but from accountants. In 1931, Capone was convicted of tax evasion and sentenced to 11 years in federal prison. He was sent to Alcatraz, from which he was released in 1939, already seriously ill with syphilis. He died in 1947 at his estate in Florida.
St. Valentine's Day Massacre
On February 14, 1929 – Valentine's Day – at 2122 North Clark Street, in the warehouse of SMC Cartage Company, a scene unfolded that would forever change America.
Seven members of the North Side gang, led by Bugs Moran, gathered in the morning at the warehouse, waiting for a delivery of smuggled whiskey from Canada. Around 10:30, a car that looked like a police vehicle stopped in front of the building. Five men got out – two in police uniforms, three in civilian clothes. They entered the warehouse, lined up the seven men against the wall, and opened fire with Thompson submachine guns.
All seven were killed or died on the way to the hospital. Frank Gusenberg – a gangster of Polish descent – survived the longest despite fourteen gunshot wounds. When police officers (the real ones this time) asked him who shot him, he famously replied: “Nobody shot at me” – and died three hours later.
The massacre shocked America. Although Capone was never formally proven to have ordered the hit – he was in Florida on the day of the massacre – it was widely believed that his men, likely under the command of Jack “Machine Gun” McGurn, carried out the execution. The public, which had previously tolerated gangsters as providers of forbidden alcohol, began to demand action.
The building at 2122 North Clark Street was demolished in 1967. Today, a parking lot and a small park occupy the site. Bricks from the original wall under which the murdered men stood were sold to collectors – some for thousands of dollars.
Where Was It? The former address 2122 N. Clark Street is now the area between buildings on the north side of the street, in the Lincoln Park neighborhood. The only physical trace of the massacre is a small commemorative plaque. It is worth noting that a nearby tree, under which – according to legend – the dog of one of the victims waited, has become an informal memorial.
Hymie Weiss – The Pole Feared by Capone
Among the dozens of gangsters who fought for control of Chicago in the twenties, one stood out for his courage bordering on madness. Hymie Weiss – born as Henryk Wojciechowski in a Polish family that immigrated to America – was the only man whom Al Capone himself said he feared.
From a Polish Family to the North Side Gang
Wojciechowski was born in 1898 in Chicago, in a Polish neighborhood on the North Side of the city. As a teenager, he adopted the American-sounding surname “Weiss” (from the German “white”) and quickly fell into the circles of street crime. He became a protégé of Dean O'Banion, the charismatic leader of the North Side Gang – the organization controlling alcohol smuggling on the North Side of Chicago.
When Torrio and Capone's men shot O'Banion in his flower shop on State Street in November 1924, Weiss took over the gang's leadership. He was 26 years old and had one mission – revenge.
The Siege of Hawthorne Hotel
On September 20, 1926, Weiss carried out the most spectacular attack in the history of Prohibition-era Chicago. A convoy of eight cars – including one with a police siren on the roof – slowly passed by the Hawthorne Hotel in Cicero, Capone's headquarters. From each car, bursts of Thompson submachine gun fire were unleashed. In just a few minutes, over 1000 rounds were fired.
Capone, who was having lunch in the hotel restaurant, threw himself to the floor. He survived by a miracle – one of the bullets passed just over his head. No one from his inner circle was killed, although several people were injured, including an innocent woman with a child on the street.
This was the boldest attack on Capone in the entire history of gang wars – and it showed that Weiss would stop at nothing.
Death at the Cathedral
On October 11, 1926, just three weeks after the siege of the Hawthorne Hotel, Hymie Weiss was returning to his office above O'Banion's flower shop at 738 North State Street, across from the Holy Name Cathedral. As he got out of his car, two shooters hidden in a nearby building opened fire. Weiss was killed on the spot. He was 28 years old.
Bullet marks on the corner of Holy Name Cathedral at 735 North State Street were visible for decades – becoming one of Chicago's grim tourist attractions. The cathedral still stands today and is one of the city's most important landmarks.
Polish Traces: In addition to Hymie Weiss, other Poles were active in the criminal world of Prohibition-era Chicago. Frank Gusenberg (born Gusenberg, from a Polish-German border family) survived the Valentine's Day massacre with 14 gunshot wounds and refused to name his killers. His brother Pete was killed on the spot. On Capone's side, there was “Polack Joe” Saltis – a boss controlling the Back of the Yards neighborhood, the center of the Polish and Lithuanian community.
Green Mill – The Most Famous Speakeasy in America
If there is one establishment in the world that embodies the spirit of Prohibition-era speakeasies and has been operating continuously for over a hundred years, it is Green Mill at 4802 North Broadway in Chicago's Uptown neighborhood.
History
Green Mill opened in 1907 as Green Mill Gardens – an elegant entertainment venue with a garden and orchestra. The name referred to the famous Parisian cabaret Moulin Rouge (Green Mill – Green Mill, Moulin Rouge – Red Mill). In the twenties, the establishment came under the control of Capone's men.
Jack “Machine Gun” McGurn – one of Capone's most ruthless enforcers (and the likely organizer of the Valentine's Day massacre) – was a co-owner of Green Mill. Under his management, the venue became one of the hottest speakeasies in the city, known for jazz, dancing, and high-quality illegal alcohol.
Joe E. Lewis – The Comedian Whose Throat Was Cut
The darkest story associated with Green Mill involves comedian Joe E. Lewis. Lewis was the star of the evening performances at Green Mill and one of McGurn's favorite artists. When Lewis decided to move to a competing club, New Rendezvous Café, in 1927, McGurn saw it as a betrayal.
On November 6, 1927, three men broke into Lewis's hotel room. They cut his throat, severing his vocal cords, and sliced his tongue. Lewis miraculously survived, although doctors gave him little chance. After months of recovery, he returned to the stage – with a permanently changed, hoarse voice that paradoxically became his trademark. His story inspired the film The Joker Is Wild (1957) starring Frank Sinatra.
Green Mill Today
Green Mill is the only establishment in Chicago that has been operating continuously since 1907 – surviving Prohibition, the Great Depression, gang wars, and gentrification. Beneath the building, remnants of Prohibition-era tunnels still exist, which gangsters used to escape from raids.
Today, Green Mill is primarily a jazz club. Live concerts take place every evening, and admission is free on weekdays. Since 1986, every Sunday, the Uptown Poetry Slam – the oldest regular poetry slam in America, founded by Marc Kelly Smith – is held here.
The interior has remained virtually unchanged – dark wood, leather booths, neon lights. Sitting at the bar, you are literally in the same spot where Capone's men once sat.
Other Famous Speakeasies from the Prohibition Era
Colosimo's Café
2126 South Wabash Avenue. The restaurant of “Big Jim” Colosimo – the first major boss of Chicago's underworld – was where the entire story began. Colosimo controlled prostitution and gambling in the South Side neighborhoods even before Prohibition. He brought Johnny Torrio to Chicago, and Torrio brought Capone. Colosimo was shot dead on the doorstep of his own restaurant on May 11, 1920 – just four months after Prohibition was enacted. His funeral was one of the most lavish in the city's history.
The Dil Pickle Club
Not all speakeasies in Chicago were gangster dens. The Dil Pickle Club in Tooker Alley, near Washington Square Park (known as “Bughouse Square”), was a bohemian speakeasy where artists, writers, anarchists, and intellectuals gathered. Founded by Jack Jones, a radical unionist, Dil Pickle combined illegal alcohol with lectures, debates, and experimental theater. It was a speakeasy for the mind – equally illegal but far less bloody than Capone's establishments.
The 606 Club
A jazz speakeasy on the South Side, popular among Black musicians and music lovers. The number 606 likely came from the postal code, although legends speak of a house number. Chicago was one of the main centers of the Great Migration – hundreds of thousands of African Americans moving from the South to the North – and jazz speakeasies on the South Side laid the foundations for Chicago jazz, which influenced the entire musical culture of the 20th century.
What You Don't Know About Prohibition in Chicago
The history of Prohibition in Chicago is not just about Capone and shootouts. Here are some facts you won't read in a typical guide:
Eliot Ness and the “Untouchables” – Truth vs. Hollywood
Brian De Palma's 1987 film cemented the myth of four heroic agents fighting Capone. In reality, “The Untouchables” was a group of eleven young Prohibition Bureau agents selected by Eliot Ness for their resistance to corruption – hence the nickname. Their main task was to destroy Capone's breweries, not to pursue the boss himself. Arresting Capone for tax evasion was the work of an entirely different group – Treasury agents led by Frank Wilson, whom Hollywood completely ignored.
Women Running Speakeasies
Prohibition opened an unexpected path to financial independence for women. In Chicago, dozens of women ran illegal establishments, often camouflaged as “tea rooms”, “beauty salons”, or “boarding houses”. Federal agents were less likely to suspect women of running speakeasies, giving them a valuable advantage. Some made fortunes – and invested them in legal businesses after Prohibition ended.
Beer Was More Important Than Whiskey
In popular imagination, Prohibition is associated with whiskey smuggling and cocktails in crystal glasses. But in working-class Chicago, the primary illegal beverage was beer. Capone controlled dozens of secret breweries producing thousands of barrels weekly. Beer was cheaper, easier to produce, and better suited to the tastes of Chicago's working class – largely composed of immigrants from Central and Eastern Europe, for whom beer was part of daily life.
Tunnels Under the City
Under Chicago lies a network of narrow-gauge railway tunnels built in the early 20th century for transporting mail and goods. During Prohibition, gangsters used parts of this network to transport alcohol and escape from the police. Beneath the Green Mill, remnants of tunnels still exist, which – according to tradition – gangsters used to flee during raids. Similar underground passages connected many speakeasies with neighboring buildings.
Thompson vs. King George
Mayor “Big Bill” Thompson ran one of the most eccentric political campaigns in American history. In addition to promises of being “wetter than the Atlantic,” he publicly threatened to if he ever visited Chicago – referencing the anti-British sentiments of Irish voters. He also promised to publicly burn history textbooks that he deemed too pro-British. He won the election.
Worth Knowing: Chicago's Prohibition has its musical monument – the musical Chicago (1975, refreshed in 1996) is set in the Prohibition-era city of the twenties. The characters Roxy Hart and Velma Kelly are inspired by real Chicago murderesses from that era.
Contemporary Speakeasies in Chicago
Chicago has one of the most vibrant cocktail scenes in America, and the tradition of hidden bars is alive here like nowhere else. Here are the best speakeasies in the city – from intimate basements to exclusive lounges with just a few seats.
The Drifter
Address: Basement under Green Door Tavern, 678 N. Orleans Street (River North)
How to Enter: Enter Green Door Tavern – a historic bar that is a landmark in itself (operating since the twenties, the building dates back to 1872, just after the Great Chicago Fire). Look for the stairs leading down. The doors to The Drifter may be closed – knock.
Atmosphere: A cramped, dark basement for a maximum of 50 people. Raw brick walls, low ceiling, flickering candles. On weekends, magic shows, burlesque, and live music take place – the venue combines the speakeasy tradition with a 1920s cabaret.
Specialty: Absinthe cocktails and mezcal-based drinks. The menu changes seasonally.
Tips: Reservations recommended, especially on weekends. The venue does not accept large groups. Dress is more elegant than casual.
The Violet Hour
Address: 1520 N. Damen Avenue (Wicker Park)
How to Enter: No sign. Look for a wooden facade with one light bulb above the door – that’s the only indication. The door may look like part of the wall. Once you enter, a heavy curtain separates the entrance from the room.
Atmosphere: Elegant, minimalist interior with high chairs and dark curtains creating private niches. The Violet Hour has strict rules: no standing (you sit or leave), no cell phones (it’s strongly frowned upon), and – which has become legendary – they do not serve Bud Light.
Specialty: Seasonal cocktail menu, changed quarterly, crafted by award-winning bartenders. The Violet Hour has won the James Beard Award for outstanding bar program – one of the most prestigious culinary awards in America.
Tips: No reservations – expect a line, especially on Fridays and Saturdays. Arrive early (opens at 6:00 PM) for the best choice of seats. Dress code: elegant but not over the top.
The Milk Room
Address: Inside Chicago Athletic Association Hotel, 12 S. Michigan Avenue (downtown, across from Millennium Park)
How to Enter: Enter the hotel, walk through the lobby, and ask about the Milk Room. Reservation required – the venue has only 8 seats.
Atmosphere: The most exclusive cocktail bar in Chicago. A tiny, intimate space where the bartender prepares cocktails just for you. It feels like being in a private club – because you practically are.
Specialty: Rare spirits and cocktails made from ingredients you won’t find anywhere else. Prices start at $30 per drink, but you pay for the experience, not the volume. The bartender often creates cocktails to order, tailored to your preferences.
Tips: Reservation mandatory, preferably a few days in advance. Maximum 2 people per reservation. The experience usually lasts 90 minutes. This is not a place for a quick drink – it’s a ritual.
The Office
Address: Below The Aviary restaurant, 955 W. Fulton Market (West Loop)
How to Enter: Reservation through ExploreTheTock.com. Enter through Aviary – the venue is located in the basement of one of Chicago's most famous restaurants, run by chef Nick Kokonas and his team.
Atmosphere: An innovative cocktail bar where drinks are treated like dishes in a Michelin-starred restaurant. Expect presentations that are as important as taste – cocktails served in ice spheres, in smoke, in vessels you have to break yourself.
Specialty: Progressive cocktails using molecular gastronomy techniques. The menu changes seasonally. This is a culinary experience, not just a regular night at the bar.
Tips: Reservation required 1–2 weeks in advance. Prices higher than average – plan for $50–80 per person. Elegant dress code.
Bordel
Address: 1721 W. Division Street (Wicker Park)
How to Enter: Entrance from the street, but easy to miss – dark facade, minimal signage. Look for a small sign and heavy doors.
Atmosphere: The name refers to a French brothel – the interior is dark, decadent, lit only by candles. Velvet couches, curtains separating tables, music ranging from trip-hop to jazz. Bordel is a place for a slow, sensual evening, not a loud party.
Specialty: The best selection of absinthe in Chicago – served in the traditional method with a spoon and sugar. Cocktails with French accents (Cointreau, Chartreuse, Lillet).
Tips: No reservations, but capacity is limited. Best on weekdays when it’s not so crowded. Ideal for a date.
Vol. 39
Address: Below the Three Dots and a Dash bar, 435 N. Clark Street (River North)
How to Enter: First, you need to find Three Dots and a Dash – hidden in an alley behind a hotel. From there, ask about Vol. 39, which is a bar hidden inside a hidden bar.
Atmosphere: An intimate space inspired by 1950s tiki bars, but with a Prohibition twist. Wooden panels, nautical accents, exotic fruits.
Specialty: Tiki-inspired cocktails, but crafted with the precision of a modern cocktail bar. Rare rums, tropical ingredients, drinks served in carved mugs.
Tips: Limited availability – not always open. Check in advance. The best option for an unexpected addition to your evening when you’re looking for something truly hidden.
Ravenswood Tap (bonus – historic venue)
Address: 1829 W. Montrose Avenue (Ravenswood)
This is not a typical speakeasy in the modern sense, but one of the oldest continuously operating bars in Chicago. Opened in 1933 – literally on the day Prohibition ended – it has retained its interior virtually unchanged since then. Wooden booths, an old bar, a neon sign. It’s an authentic piece of Prohibition history, not a modern stylization.
Visitor Tips
Practical Advice
- Reservations: Milk Room and The Office require reservations in advance. Violet Hour and The Drifter – recommended on weekends, not necessary on weekdays. Bordel and Vol. 39 – no reservations, come early.
- Dress Code: Most Chicago speakeasies prefer smart casual – you don’t need a suit, but shorts and flip-flops are definitely a no. The exception is Green Mill – you can enter in whatever you want.
- Budget: Cocktails in speakeasies typically cost $16–22. Milk Room and The Office range from $30–50 per drink. Green Mill is the cheapest option – beer for $6–8, cocktails for $10–14.
- Transport: Chicago has excellent public transport (CTA “L”) and buses. Uber and Lyft work seamlessly. Don’t drive after drinking – penalties in Illinois are severe.
- Tipping: In cocktail bars, the standard is 20% or $2–3 per drink. Bartenders in speakeasies put in significantly more effort than in a regular bar – appreciate that.
Suggested Evening Itinerary
Option 1: Classic Chicago (4–5 hours)
- 6:00 PM – Green Mill (Uptown): Start with history. Arrive early, sit at the bar, feel the atmosphere of a venue that remembers Capone. Order an Old Fashioned – the same drink served here a hundred years ago. Enjoy the jazz (concerts usually start at 8:00 PM, but the atmosphere is excellent from opening).
- 8:00 PM – The Violet Hour (Wicker Park, ~25 min by subway): Move on to modern classics. Two signature cocktails in elegant silence.
- 10:00 PM – Bordel (Wicker Park, 10 min walk): End the evening with an absinthe cocktail by candlelight. A perfect finale.
Option 2: Luxurious Evening (3–4 hours)
- 7:00 PM – The Milk Room (Michigan Ave): Start at the most exclusive bar in the city. Two cocktails – the bartender will tailor them to your tastes.
- 9:00 PM – The Drifter (River North, 15 min walk): Descend to the basement under Green Door Tavern. A magic or burlesque show with a mezcal cocktail.
- 11:00 PM – Three Dots and a Dash / Vol. 39 (River North, 10 min walk): A tropical finale in a hidden bar inside a hidden bar.
Option 3: Following the Prohibition Trail (All Day)
- Morning: Walk through Lincoln Park – visit the site of the Valentine's Day massacre (2122 N. Clark St). Today it’s a parking lot, but the plaque and the atmosphere of the place are impressive.
- Noon: Holy Name Cathedral (735 N. State St) – look for bullet marks on the corner, where Hymie Weiss was killed. Lunch in the area.
- Afternoon: Chicago History Museum (Clark St and North Ave) – an exhibition on Prohibition and gangsters, including personal items of Capone.
- Evening: Option 1 or 2 above.
Seasonality: The best time to visit Chicago's speakeasies is in the fall (September–November) – the weather is pleasant, summer tourists have left, and bars introduce autumn menus. Avoid winter (December–February), when temperatures drop below -15°C, and the wind from the lake is piercing – although, it must be said, descending into a warm, hidden bar has a special charm then.
Chicago and Speakeasies – A Legacy That Lives On
No other American city is as closely associated with Prohibition as Chicago. It was here that alcohol and crime shaped politics, architecture, and culture for decades. Echoes of those times can still be heard today – in the jazz music emanating from the Green Mill, in the underground tunnels beneath the city, and in the bullet marks on the wall of the cathedral.
For a Polish visitor, Chicago holds particular significance. It was here that Henryk Wojciechowski – the son of Polish immigrants – became one of the most powerful men in America. It was here that Polish workers from Back of the Yards and Bridgeport created communities where illegal alcohol production was a normal part of life – just like in Hamtramck near Detroit. And it was here, in candlelit speakeasies, that Poles, Italians, Irish, and Jews sat side by side at the bar – united by a shared love for forbidden drink.
Contemporary speakeasies in Chicago pay homage to this history. You enter through hidden doors, sit in a raw-brick basement, order a cocktail prepared from a recipe a hundred years old – and for a moment, you feel like those who sat here before you, when the very doors and the drink itself were illegal.
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