The Grand Avenue entrance to Richard's Bar. (Lenny Gilmore / RedEye )
491 N. Milwaukee Ave. 312-733-2251
Looks like: A neon-lit bar with a packaged beer fridge
Smells like: Cigarette smoke
Sounds like: Frank Sinatra
It's a bit reductive to call Richard's Bar a "dive." To me, dives are places one slinks into with a hat pulled down low, hoping only for cold beer and anonymity. Before every watering hole that didn't have a "curated cocktail program" was labeled a dive, there existed gems called neighborhood bars. There, you could get a cheap drink, meet your friends who live nearby, and maybe develop a "Hey, how you doing?" rapport with the bartender. Richard's still acts as a neighborhood bar for River West residents and industry types leaving Fulton Market kitchens at 1 a.m., though it's worth a visit even if you're neither.
To get one detail off the table: Yes, it smells like cigarette smoke inside and after 20 minutes, your clothes will, too. Not mad? Read on.
I haven't yet had the chance to drink at a bar with my grandfather—Pop-Pop, the offer is on the table—but if we ever plan to meet over Schlitzes, we're going to Richard's. My grandpa would blend in with the older men laughing with their wives under the huge "Goodfellas" banner that festoons one wall, or the post-shift worker in a Welding.com T-shirt slowly sipping a beer. That's not to say that my friends and I in our office beigery feel out of place. I have a suspicion that not much fazes the regulars at Richard's, not even the earnest newbie who asks what beers are on draught. (Answer: None. Bottles and cans only.)
I would be doing a disservice to the bar in dwelling too long on its curiosities, but they are charming: hard-boiled eggs for purchase (75 cents), the most incredibly '80s Chicago International Film Festival poster in the women's bathroom and autographs from seemingly every Italian-American actor of the last half-century. And a loud jukebox. And an overburdened coat rack.
These are the quirks you mention if you're telling someone about Richard's for the first time, but they're not the reasons you'd return to the bar. You go back for the cheap High Life, the proximity to lots of public transit, the unbelievable hours (8 a.m. to 2 a.m. most days), and mostly, for the feeling that you could bring anyone to this bar—your cool co-worker, long-time friends, a date that's unexpectedly still hanging out with you into the wee hours of the morning. How many dive bars can say that?
Read about the other bars and restaurants in our series, The Essentials, at redeyechicago.com/essentials. email@example.com | @redeyeeatdrink