The Run Down

We’re going on a night time adventure in Roscoe Village for burgers, cocktails, live jazz, and a comedy show in the back of a bar. This isn’t any comedy show. The performers here are the type where 1 or 2 years down the road you’ll be seeing them on a Netflix comedy special and you can brag to all your friends that you discovered them well before they got big. So kudos to your future self for being able to do that.

1. Burgers @ The Region

2. Cocktails and Jazz @ Hungry Brain

3. Chicago Underground Comedy @ Beat Kitchen

1. The Region

While Chicago is known for its hot dogs, the burger scene is something to celebrate, too. This trip starts with a visit to The Region, a BYOB burger and shake shop that, in 2017, brought their Northwest Indiana-style burgers to Roscoe Village. That means patties are smashed super thin and grilled until the edges get a chip-like crisp. They’re then topped with relish, onion, and a secret sauce.

If you were to teleport their storefront back to the 1950s, it might fit right in. Their indoor space has a walk-up counter and a few high-top tables by the window, but their sidewalk patio is where it’s at when the weather cooperates.

Here’s the star of the show. Since coming onto the Chicago burger scene, they’ve slowly made their way onto all the top Chicago burger lists. The Chicago Tribune has it ranked #5 overall, besting well-known places like Au Cheval and DMK Burger that have been longtime representatives on these lists.

2. Hungry Brain

After burgers, our next stop is the Hungry Brain, a nondescript cocktail lounge. There isn’t any clear signage out front, so you may pass it a few times before navigating to the big green door that will take you inside.

Once inside, there’s this speak-easy vibe, and right by the front of the bar is a stage with a baby grand piano, a mic, and a drum set.

We were there on a Tuesday night when they had famed Chicago Jazz pianist Erwin Helfer performing a set. With Erwin playing on the piano, the hushed audience, and the red lights illuminating the stage, grabbing a cocktail at the bar feels like you’re in a scene from La La Land.

Erwin has been playing since the 1950s, recorded several albums, and traveled the world performing his “boogie-woogie” blues and jazz style.

Lastly, here are some general notes about the place if you plan on visiting.

– Cash only
– Closed on Mondays
– Here is their calendar of performances. It’s a mix of live music, comedy, theater, and everything in between.

3. Chicago Underground Comedy

After a few cocktails at Hungry Brain, we’re headed down the street to see Chicago Underground Comedy, a stand-up and sketch show held in the back of the Beat Kitchen restaurant/bar. This show has been going on for over ten years and attracts some big-name stand-up acts. Not to name-drop, but TJ Miller and Hannibal Burress have been known to drop in from time to time.

When we went, the stand-up comics included a current SNL writer, a main stage Second City performer, and a few up-and-coming comics from LA and NY. You’re getting quality performers here, and not some randoms for an open mic set.

A few last notes before we move on.

– The show is every Tuesday. Doors open at 8:30 pm and starts at 10 pm
– Tickets are $10.
– Link to their Facebook page for more info.