Best Oddly Shaped Bars In Chicago

April 24, 2012 2:00 PM

By Dan Morgridge

So you’re a bar expert. You know all the best local dives. You’ve written the name of the cutest bartender with little hearts over the eyes. You probably even know the best place to go for a good Malort cocktail. Congrats on all that. Now let’s focus on something a little more important, shall we? Feng Shui. Atmosphere. A vibe, man. What bars have the right stuff? I’m not talking about the right lights or recycled this and that for the materials. I’m talking about space here. A really funky one can either make for your dream bar, or at least add a spoonful of quirky to whatever concoction you’re downing. Here’s our picks for the most bewilderingly blueprinted bars in Chicago.

matchbox 4 Best Oddly Shaped Bars In Chicago

(credit: The Matchbox

The Matchbox

770 N. Milwaukee Ave.
Chicago, IL 60642

When there’s a crowd at the bar, it’s easy to feel like the walls are closing in on you. Of course, if you’re moving deeper into the Matchbox, they actually are. Sister restaurant to the Silver Palm, Matchbox has been cramming people into a corner for over 75 years. Of course, it’s owned by the same people who own the Silver Palm, which has as standard a floor plan as you can get for a train car turned into a restaurant. Six corner intersections make for fun designs! (More on that later.)


1951 W. Dickens Ave.
Chicago, IL 60614

If you ever felt like your first post-college apartment was for all intents and purposes a bar, you’d be one step away from Danny’s. A series of rooms with little sense of flow or purpose, Danny’s seems like someone decided that they’d open a bar and only had enough construction money to add one. The existing satellite rooms offer delightful privacy, and the one central dance area, for better or worse, is a black hole of entangled limbs: some fighting towards the bar or bathroom, and some just attempting to dance.

Feel free to also check out Danny’s monthly reading series.

screen shot 2012 04 17 at 5 13 28 pm Best Oddly Shaped Bars In Chicago


Long Room

1612 W. Irving Park Rd.
Chicago, IL 60613

Long Room continually wins the “brutal honesty” award for bar names. Granted, there’s some booths somewhere in there, and purportedly even a patio. But that’s like saying there’s probably some ground down at the bottom of Challenger Deep. You’ll never make it past the bar. The 60-foot bar hosts no less than 38 barstools, which, doing the math, would take even Usain Bolt two seconds to get from one end to the other. And since he probably can’t mix cocktails as he runs (or CAN he), you better just enjoy the ambiance and get to know the people in your little stretch of infinity.


491 N. Milwaukee
Chicago, IL 60610

To call Richard’s a dive bar would be a grave mistake. One pictures a sad little watering hole turned grey from years of steady regulars sidling up to the bar and never once swiveling their seat, maybe featuring an ill-advised jukebox selection that only gets played when some snarky 22-year-old enters and declares the place awesome (right after becoming mayor of the place on Foursquare). Richard’s defies that. Like a long, leering glance from an octogenarian, Richard’s stretches out across the southeast corner of Grand and Milwaukee, offering Jay’s chips, pickled eggs, kindly (or otherwise) old bartenders and a boggling mix of the most fun, talkative, non-traditionally attractive group of ageless outcasts you’re likely to meet in the city. Is it because the bar is on some weird timeless mystery spot? Or is it just because it’s one long thin strip of madness, with nowhere to hide?

Rainbo Club

1150 N. Damen
Chicago, IL 60622

There’s a stage, sure. You can’t get to it. There are paths towards it, but good luck getting through that narrow L. And the group using the photobooth has the other area blocked. Okay, to the main area. There’s a couch! One. A regular couch. Is this the calm area? With a pinball machine right next to it? Also the windows are either paintings or dioramas, and you’ll never see natural light here. And all the tables are circle booths, and you’re not getting in one of them anytime soon. Even the one with coats on all the hangers, but no people in it – they’re hovering nearby and ready. Rainbo isn’t the weirdest layout at first glance, but trust us – you’ll find yourself standing at the center of the room and afraid to move anywhere else within 10 minutes if you don’t know what you’re doing.

Dan Morgridge is a writer from Chicago who once wandered by the “bar” consisting of the alley next to City Soles, and he does not recommend it.

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