Richard’s Bar

Chicago, Illinois

Field Note

Chicago’s rich history and deep dive bar inventory require that a bar offer something pretty unique to stand out among seemingly endless drinking options. Richard’s Bar in the city’s River West neighborhood does just that, combining a rumored ‘family’ connection, decades of history and a surprisingly strict no photos policy to create one of the city’s most distinct drinking atmospheres.

Opened in 1926, Richard’s Bar carries with it a bit of mystery thanks to rumored ties to the mob with city documents listing the business’ owners as Susan Dominic, sister to a man once called a ‘known mob associate.’ The massive Italian flag painted on the side of the building and a set of posters inside featuring Sinatra and a scene from Goodfellas do little to dispel the notion. But more so than any rumored connection, Richard’s Bar has exhibited an air of defiance over its history that creates its own specific aura.

Most notably, and despite a faded, brown sign over the bar that reads ‘No Smoking,’ Richard’s Bar has long rebelled against the 2008 Chicago indoor smoking ban. Fines have been levied and paid over the years, but that has done little to stop the Chicago dive bar from not just allowing smoking but selling packs of cigarettes inside. During the COVID-19 pandemic, a similar spirit was applied to the city’s public gathering ban with a number of complaints levied by neighbors against Richard’s Bar for hosting drinkers inside.

Whether it is this gentle push against authority or the nature of the bar’s ownership, another sign reading “No Photos” hangs above the bar and this reviewer was swiftly reminded of its presence on a recent visit. Only adding to the sting of correction is the fact that all Richard’s Bar bartenders are decked out in strikingly clean and classic uniforms, the look very much in line with the historical pedigree of the structure.

But the space inside is beautiful enough to warrant any risk of photographic rebuke, thanks in large part to an epic, faded, old style sign above the bar listing available beers alongside their on-premise and to-go prices. Almost resembling a vintage train departure listing, each intricate letter and number perched atop a seemingly ancient plastic backing feels like a callback to one of the many decades Richard’s Bar has endured since opening before and enduring Prohibition.

Once named Tischer’s Bar, the space is no stranger to the occasional violent incident, serving as site to a 1976 holdup and homicide as well as a more recent stabbing outside its front door that sparked a handful of protests and calls for investigation. But despite those isolated moments, the Richard’s Bar vibe is more serene on most nights than chaotic, the single-room layout only occasionally dipping into high density drinking on the weekend evenings when non-regulars come to get a glimpse of the space.

The space’s 14 bar stools line a small bar in the single room accessed by a pair of entries, one on either side of the Richard’s Bar building that straddles Grand & Milwaukee Avenues. Where the Grand Avenue entrance sports its Italian flag mural, the Milwaukee Avenue entrance offers something completely different in the way of opaque glass blocks under a simple red awning and equally simple illuminated sign plainly reading “Richard’s Bar.”

Maybe most impressively, despite the cloud of cigarette smoke that tends to hang in the air at Richard’s Bar, the space feels clean, almost sterling. A reflective tin roof bounces light off of polished surfaces and opaque glass blocks, creating a bright, almost inviting vibe. Pricing at Richard’s Bar is entirely affordable by Chicago standards, an array of can & bottle options topping out at $5 each. Each drink is rung up on a vintage cash register that sits among a sea of liquor options and a handful of vintage beer signs.