What Is The Best Speakeasy In Chicago?

The Green Mill Cocktail Lounge in Uptown is the one Chicago speakeasy claim that survives a fact check. The bar at 4802 N. Broadway retains documented Prohibition-era ties to Al Capone, including the booth reputed to be his favorite, and it still serves on the same corner every night of the week. Most other "speakeasies" in the city are modern cocktail bars wearing a costume. The honest way to drink the history is to combine a verified landmark like the Green Mill with a guided crawl, and the Costumed Haunted Pub Walk from Glascott's Saloon exists for exactly that reason. If Capone's favorite booth has you wondering how he stacked up against the other bosses of his era, our ranking of Chicago's most powerful gangsters separates the real power players from the legend.

The Green Mill Cocktail Lounge at 4802 N. Broadway St. is the best speakeasy in Chicago. It operated through Prohibition, carried real ties to Al Capone, and still opens tonight, with hours running Monday to Thursday 4 p.m. to 1 a.m., Friday 4 p.m. to 4 a.m., Saturday 1 p.m. to 5 a.m., and Sunday 2 p.m. to 1 a.m.

The distinction matters because the word "speakeasy" gets stretched across half the cocktail menus in the city. A bar hidden behind a phone booth or a pastry shop is a modern cocktail bar with a theme, and there is nothing wrong with that. But a reader asking for the best speakeasy is usually asking for the room where the history actually happened, and in Chicago that shortlist is very short. The Green Mill poured through the 1920s, and its Prohibition-era ties to Capone, including the booth said to be his favored seat, are part of its current identity, as noted on its listing in Time Out Chicago's bar guide.

The runner-up tier works differently. The Congress Plaza Hotel on South Michigan Avenue opened just before the 1893 World's Fair as the Auditorium Annex and is frequently claimed to be one of the most haunted buildings in Chicago, a reputation rather than a proven fact, and its bar gives you a drink inside a building with genuine pre-fair bones. The Palmer House Hilton carries reports of phantom footsteps and a woman in period clothing in its corridors, reports collected by haunted-hotel trackers rather than by historians. Both are places to drink near history. The Green Mill is the place to drink inside it. If you'd rather visit several of these haunted bars in one night, our guide to Chicago's haunted pub crawls maps out routes that tie them together.

There is a practical catch, and it shapes the rest of this article. The Green Mill sits in Uptown, far from the Loop hotel strip where most visitors stay, and a plain taxi ride there gets you a great bar and no stories on the way. That gap is what the haunted pub tour industry in Chicago exists to fill. The Haunted Chicago Booze and Boos Ghost Walking Tour, a costumed pub walk rated 4.9 across 338 reviews, moves between real Lincoln Park bars with a guide telling the darker history between stops, from $35.87 per person. It is the format that turns a bar list into an evening.

Which Prohibition Survivors Can You Actually Drink In Tonight?

Three kinds of place deliver a real speakeasy night in Chicago: the Green Mill, the one true Prohibition survivor still pouring; the grand hotel bars of the Loop, including the Congress Plaza Hotel and the Palmer House, where you drink inside documented historic buildings; and the modern hidden-entrance cocktail bars, which are themed but excellent. A haunted pub walk stitches the second and third categories into one guided evening.

The Green Mill needs the least introduction and the most travel planning. Hours are Monday to Thursday 4 p.m. to 1 a.m., Friday 4 p.m. to 4 a.m., Saturday 1 p.m. to 5 a.m., and Sunday 2 p.m. to 1 a.m., and it sits on the CTA's Red Line at the Lawrence stop, which is the honest answer to how you get home at 4 a.m. The room is famous for jazz as much as for gangsters, and the Capone booth is pointed out the way other bars point out a signed photo. Nothing about the visit promises a ghost, because nothing should.

The hotel bars cluster where visitors already sleep. The Congress Plaza Hotel at 520 S. Michigan Ave. is the meeting point for an entirely different kind of night out, and its history is real even where its hauntings are only reputations. The building opened as the Auditorium Annex for the 1893 World's Fair. The Palmer House Hilton's ghost reports, footsteps in the corridors and a woman in period dress, are catalogued by enthusiasts rather than archives, but the building itself is a rebuilt-after-fire landmark on State Street, and its bar is a legitimate place to spend an October evening.

The themed modern speakeasies are the third category, and dismissing them entirely would be a mistake. Hidden entrances, unmarked doors and password rituals are theater, but the theater is fun and the cocktails are frequently better than anything poured in 1929. What they cannot give you is the line between the barstool and the history, which is the exact thing a costumed guide can. This is why the pub-crawl format earns its ticket price: the Booze and Boos walk caps its groups at 12 people, requires a minimum age of 21 with at least two adults to book, and runs about 2 hours 30 minutes from its meeting point at Glascott's Saloon in Lincoln Park, with free cancellation listed on the operator's page.

Wondering whether a guided pub walk beats barhopping on your own? The listing for the costumed Lincoln Park pub walk shows free cancellation, so a change of plans late in the day does not cost the ticket. Check availability on the operator's live listing before locking an evening in.

How Do Haunted Pub Tours Fold Speakeasy History Into One Night?

A haunted pub tour in Chicago runs 1 to 2.5 hours, costs $26 to $35.87 per person, and moves a small group between real bars while a costumed or character guide tells the city's darker history between stops. The Booze and Boos walk is the flagship at 2 hours 30 minutes, capped at 12 guests, meeting at Glascott's Saloon, while shorter ghost walks cover the same neighborhoods without the bar stops.

The mechanics are simple and worth understanding before you book. The group meets at a named bar, in this case Glascott's Saloon in Lincoln Park, and the route strings together stops where the guide delivers the stories tied to each address. Drinks are bought separately at each bar, since none of the tours listed here includes drinks in the ticket, and the 2.5 hour window is generous enough that the evening feels like a night out rather than a march. The costume element sets the tone closer to theatrical than terrifying, and the 4.9 rating across 338 reviews suggests the balance lands.

If you want the same neighborhoods without the bar stops, the walking formats split neatly. The Embers of the Windy City ghost walk is a 1-hour Lincoln Park route from $26 per person, rated 4.4 across 129 reviews, meeting at the Tin Man statue in Oz Park with a group cap of 15. It covers the park's buried history, and Lincoln Park genuinely has some: the land was once the city's Old City Cemetery, with an estimated 35,000 burials relocated and the Couch mausoleum still standing behind the Chicago History Museum as the visible reminder. A short cemetery-to-park walk and a long pub crawl cover adjacent slices of the same neighborhood.

The Loop answers with its own formats. The adults-only Wind and Souls ghost walk, $34.99 per person and rated 4.2 across 46 reviews, runs 1 hour 30 minutes from outside the Chicago Theatre with a strict adults-only door policy, which makes it a different kind of grown-up evening from a pub walk. Group size runs to 30. The choice between a Loop route and a Lincoln Park route usually comes down to where your hotel is, and both neighborhoods carry enough documented history to fill an hour without inventing anything.

The formats stack up like this:

Between the two, the shorter walk is the cheaper audition for the format. At $26 per person for an hour, it tells you whether guided storytelling works for your group before you commit an evening and a bar budget to the full crawl.

What Gangster Landmarks Sit Near The Old Speakeasy Quarter?

The Loop and River North hold the densest cluster of verified gangster landmarks within walking distance of the historic hotel bars: Holy Name Cathedral's bronze doors still show bullet holes from the 1926 murder of Hymie Weiss, the Biograph Theater at 2433 N. Lincoln Ave. marks where John Dillinger was shot on 22 July 1934, and the St. Valentine's Day Massacre site at 2122 N. Clark St. killed seven men on 14 February 1929.

The bullet holes are the detail that surprises people. Holy Name Cathedral at 735 N. State St. is an active parish, open to the public, and the damage from the Hymie Weiss shooting remains visible on its bronze doors nearly a century later. You can stand on the sidewalk and see it for free, which makes it one of the best value stops in the city's gangster geography. The gangster walking tours that work River North and the Loop pass through exactly this territory, and the Gangsters and Ghosts guided walking tour, $31 per person and rated 4.7 across 1,878 reviews, is the volume leader here, running about 2 hours from outside Hoyt's Tavern on the riverfront and entering the Palmer House itself along the way. The full index of guides sits on Chicago Ghost Tours.

The Biograph Theater carries the most cinematic story. John Dillinger was shot by federal agents outside the theater at 2433 N. Lincoln Ave. on 22 July 1934, an event documented in detail by the theater's historical record and by the Chicago History Museum's own writing on Dillinger's complicated legacy. The building still stands and operates as a working theater, which means the marquee you photograph tonight belongs to the same building whose alley witnessed the 1934 ambush.

The massacre site is the sobering one. The garage at 2122 N. Clark St. where seven North Side Gang members and associates were killed on 14 February 1929 was demolished in 1967, and today the address is a lawn and parking area behind a wrought-iron fence beside a Chicago Housing Authority senior building, with no plaque or marker of any kind. Tours that reference the site are pointing at an absence, which is itself the honest story: the city erased most of this geography on purpose. The tone on any good tour stays factual and respectful at these stops, and the gangster walks listed here, including the 90-minute Capone and ghosts walk at $35 per person, rated 5.0 across 446 reviews, treat these addresses as history rather than spectacle.

One address needs a caution flag. Al Capone's former residence at 7244 S. Prairie Ave. is a privately owned two-flat, visible from the public street but not open to visitors, and December 2025 reporting confirms exactly that arrangement. Bus tours point it out from the street and move on, which is the correct etiquette. For readers planning a wider trip around Capone's city, the companion piece on Capone's favorite Chicago bar goes deeper on the Green Mill connection.

The 2-hour gangster walk is the format that connects the speakeasy story to the street geography, with children 6 and under joining free per the listing. Check availability for your dates on the live listing.

How Much Does A Speakeasy Night In Chicago Cost?

A guided haunted pub walk runs $35.87 per person for 2.5 hours, ghost walking tours run $26 to $35 per person, and gangster walks run $31 to $35 per person, all from the tours on this site. Add your own bar tab on top for any tour with stops, since no listing includes drinks, and the bus formats run $48 to $60 per person for wider geography.

The table below puts the drink-adjacent formats side by side, using only published prices.

Budget the evening honestly. The ticket is the floor, not the ceiling, on a pub walk: each stop means a drink bought separately, and a 2.5 hour route with multiple bars adds a real tab on top of the $35.87 entry. The trade is that you are not paying for a seat, you are paying for a route, a cap of 12 fellow guests, and a guide who knows which addresses carry real history. Solo barhopping through the same neighborhoods costs less in dollars and more in research, and you arrive at each door with no story attached.

The bus formats are the third budget tier and solve a different problem. The Crime and Mob coach tour, $49 per person and rated 4.6 across 3,603 reviews, covers 1.5 to 2 hours of wider geography from a Streeterville pickup, and the 3-hour evening ghost bus from the Congress Plaza Hotel bar, $59 per person and rated 3.8 across 152 reviews, is the closest thing to a rolling speakeasy night, since it starts inside a hotel bar with its own haunted reputation. Every tour listed here shows free cancellation, so the financial risk on any of these is low if plans shift. Readers weighing the full spread should also skim the haunted pub crawl guide for Chicago, which breaks down the crawl format in more detail.

When Is The Best Season For A Speakeasy Night In Chicago?

October is the peak season for haunted pub tours in Chicago, anchored by Halloween on Saturday 31 October 2026, and the seasonal river and zoo events run on fixed dates through that month. The walking and pub tours listed here run year-round, with the Gangsters and Ghosts walk departing daily at 11 a.m., 1 p.m., 4 p.m. and 8 p.m., so an off-season speakeasy night is entirely doable and often quieter.

The October calendar is dense enough to plan around. The Haunted Tours of Historic Prairie Avenue run on October 30 and 31, 2026, on the same South Loop street where the Prairie Avenue ghost hunt meets at Glessner House, a 2-hour investigation-style tour at $37.50 per person with no reviews yet on its listing. The First Lady's Creepy Cruise runs through November 22, 2026, with 90-minute departures on Fridays, Saturdays and select Thursdays and Sundays, and its fall 2026 route highlights the Eastland disaster site on the river, where the SS Eastland capsized on 24 July 1915 with 844 passengers and crew killed, tied to a dock between Clark and LaSalle Streets.

Winter gets dismissed too quickly. The pub walk format barely notices cold, since the design alternates outdoor storytelling with indoor bar stops, and the audience thins after Halloween. The trade-off is Chicago winter weather itself: evening lows drop hard from November onward, and the walks run rain or shine, so the clothing choices matter more than the calendar. The evening ghost walk outfit guide for Chicago covers the practical side, and the answer to whether a walk works in deep winter is yes, with layers.

Should you book ahead? For October Saturdays, yes, without hesitation: seasonal events across the city sell out in advance, and the zoo's Haunted History Tours explicitly sell out with no gate sales, which tells you what late-October demand looks like citywide. For a February Tuesday, the 8 p.m. Gangsters and Ghosts departure will have room. The advance booking question for Chicago haunted tours runs the numbers, but the short version is that speakeasy-adjacent evenings follow the same rule as the bars themselves: the popular nights are the crowded nights.

Common Questions About Chicago Speakeasies

What Is The Best Speakeasy In Chicago?

The Green Mill Cocktail Lounge at 4802 N. Broadway St. is the best documented choice, with Prohibition-era ties to Al Capone, his reputed favorite booth, and live hours tonight including 4 a.m. Fridays and 5 a.m. Saturdays. Everything else billed as a speakeasy is either a themed modern cocktail bar or a historic hotel bar, both enjoyable, neither the real article.

Can You Visit Al Capone's Favorite Bar In Chicago?

Yes, the Green Mill is open to the public nightly and the Capone connection is part of its published identity. Al Capone's former home at 7244 S. Prairie Ave. is a different matter: it is privately owned, visible from the street only, and not open to visitors.

Do Any Chicago Tours Include Drinks At Speakeasy Bars?

No listing on this site includes drinks in the ticket price. The Costumed Haunted Pub Walk from $35.87 per person stops at real bars where drinks are bought separately, and a 2.5 hour guided route replaces the research a solo crawl would demand.

Are The Gangster Landmarks Near The Speakeasies Free To See?

Most are. The bullet-scarred bronze doors of Holy Name Cathedral, the Biograph Theater facade where Dillinger was shot in 1934, and the unmarked Valentine's Massacre site at 2122 N. Clark St. are all visible from public sidewalks at no cost. Guided walks add the stories and the route.

Is A Haunted Pub Tour In Chicago Worth It Over Barhopping Alone?

If you want the history attached to the addresses, yes. The Booze and Boos walk costs $35.87 per person, caps groups at 12, runs 2 hours 30 minutes, and carries a 4.9 rating across 338 reviews, with free cancellation listed. A solo barhop gets you the same drinks with none of the context.