The Run Down

This guide starts with drinks at an exclusive basement speakeasy in Lakeview. Afterwards we have two live shows to choose from depending on your mood. The first is a theater in Wrigleyville focused on showcasing sci-fi themed productions. The second option is one of Chicago's most iconic comedy institutions. Here are the details.

1. Drinks @ Room 13

2a. Sci-Fi  @ Otherworld Theatre

2b. Improv @ The Annoyance Theatre

1. Room 13

There’s a lot of interesting basement speakeasies in Chicago, but there are few that take the speakeasy concept as seriously as Room 13. Located beneath the Old Chicago Inn, Room 13 is a members-only speakeasy that requires a secret password to enter and enforces a cocktail/business casual dress code.  Here are some notes to get you started.

– Open from Wednesday – Saturday, 5pm – 1am
– While this is a members-only club, you can visit a few times a year as a non-member. E-mail them and let them know you want to visit. They’ll give you the password for that night.

If you’re facing Old Chicago Inn, then head to the left and you’ll see a set of outdoor stairs leading you down. Follow that staircase.

A red light illuminates this basement entryway, and you’ll come upon a door with a viewing slot at eye-level. Knock on the door and say the password.

Once you’re in, the place has a cozy and intimate feel. There are lounge chairs and cocktail tables lined up against the wall and a small bar in the corner tended by the resident mixologist. Cocktails are the name of the game here. When you place your order, not only will you get a stiff drink, but the bartender has lots of stories to share behind each one.

2. Otherworld Theater

After drinks, we’re ready to see a show. We’ve got two different places on the agenda, depending on the mood. First up is Otherworld Theatre. Otherworld Theatre is located just north of Wrigley Field in a small performance venue. Before this venue was Otherworld Theatre, it was Public House Theatre, and before that, it was Live Bait Theatre in the late 90s – point being is that this venue has been a creative space for performers for a very long time.

What’s different about Otherworld Theatre, however, is that it’s one of the only theatre companies in the nation that’s dedicated to producing high production science fiction and fantasy plays. They bring these wonderfully imaginative stories onto the live stage, which have garnered much deserved praise from critics.  Here are some notes to get you on your way.

– They have a changing series of different short-run productions, and a few weekly standing shows. You can check out their event calendar for what’s playing now.
– Prices range from $10 – $20
– Shows run Thursday – Sunday


2b. The Annoyance Theatre

If science fiction and fantasy plays aren’t up your alley, we’ve got a second option for you. Right down the street from the Room 13 speakeasy is the The Annoyance Theatre — part of the holy trinity of Chicago improv theaters.

– You can catch a show every night of the week. Here’s their calendar.
– Proof of vaccination required.

To get here, you’ll enter the building and take stairs to the second floor. As you step into their space, it opens up to a bar lounge with massive windows that overlook all the action below on Belmont Ave.

This is the hall leading to two different performance spaces. They have a main stage where you can catch more conventional improv and sketch acts and they have a small theatre where you’ll find more experimental bits.

A lot of well know performers like SNL’s Aidy Bryant and funny man Andy Richter have graced the stage. Who knows, you just might witness the next comedy superstar in the making.