Explore your world
Outside of Steppenwolf Theatre | © McDuff/WikiCommons
Outside of Steppenwolf Theatre | © McDuff/WikiCommons

A Guide To Art And Entertainment In Chicago's Old Town

Picture of Alyssa Reyes
Updated: 15 April 2016
The Old Town neighborhood, on Chicago’s North Side, is a collection of the best that the city has to offer. With beautiful scenery, sky-high buildings, charming boutiques, and a variation of restaurants, it is obvious why locals and visitors flock to the neighborhood. The Old Town neighborhood is also another great spot in the city to experience art and see memorable shows. Here is your guide to art and entertainment in Chicago’s Old Town neighborhood.

Floating World Gallery

Judging from its sleek yet minimalist exterior, the Floating World Gallery may not seem like the typical art gallery, but once inside, the gallery comes alive with an impressive collection of art. The Floating World Gallery contains a huge collection of 20th-century Japanese art. For the last two decades, the gallery has displayed the work of Japanese artists and Japanese-inspired Western artists. Works from artists like Tsuchiya Koitsu, Kawase Hasui, and Katsushika Hokusai are featured at the gallery, among countless other iconic Japanese artists. Most recently, the gallery showcased the exhibit Creating What Has Never Been, which focused on post-war pieces. Visit the Floating World Gallery and experience the best of Japanese art the city has to offer.

Floating World Gallery, 1925 N Halsted Street, Chicago, IL, USA, +1 312 587 7800

UP Comedy Club

The UP Comedy Club in Old Town is relatively new to Chicago, but it has quickly established its spot as one of the best comedy clubs in the city. Guests can enjoy food and drinks in the cabaret-style venue while watching sketches and improv shows. UP has welcomed comedians from Jerrod Carmichael, Al Madrigal, and John Mulaney. Upcoming shows include the Laugh Out Loud Tour, The Second City’s Fast Loud & Funny, and Improv All-Stars. Don’t miss out on this true Chicago experience.

UP Comedy Club, Piper’s Alley, 230 W North Avenue, Chicago, IL, USA, +1 312 662 4562

courtesy of UP Comedy Club

courtesy of UP Comedy Club

Old Town Triangle Association

The Old Town Triangle Association offers a creative outlet not only for residents of the Old Town neighborhood but also for anyone looking to have fun learning experience about art. Express yourself through art from dramatic oil paintings to whimsical watercolor pieces. The Old Town Triangle Association works to promote and teach art to the community through art gallery showings and the annual Old Town Art Fair. The current exhibit at the Old Town Art Center is Saints and Legends by Norman Baugher.

Old Town Triangle Association, 1763 N North Park Avenue, Chicago, IL, USA, +1 312 337 1938

Steppenwolf Theatre

Aside from the deep dish pizza and sports teams, Chicago is also known for its growing theatre scene. The Steppenwolf Theatre in Old Town is no stranger to the scene. The Steppenwolf is already an established theatre company known for putting on riveting stage productions, as well as being the place for aspiring performers to launch their careers. Venture to the Old Town neighborhood and experience some of the best ensemble-led stage productions. Steppenwolf’s upcoming lineup includes Mary Page Marlowe, Constellations, and Between Riverside and Crazy.

Steppenwolf Theatre, 1650 N Halsted Street, Chicago, IL, USA, +1 312 335 1650


A Red Orchid Theatre

A Red Orchid Theatre is an ensemble-based theatre with Hollywood roots. A Red Orchid Theatre was co-founded by Michael Shannon in 1993, and since then, the theatre has become a spot for aspiring writers, directors, and performers to come together and produce dramatic plays. The theatre specializes in stage productions written by local Chicago playwrights. Support local artists and see a show at the Red Orchid Theatre. Sender is now showing at the theatre, which tells the story of a man thought to be dead who returns back to his home and is forced to confront the dire situations he has returned to.

A Red Orchid Theatre, 1531 N Wells, Chicago, IL, USA, +1 312 943 8722

Zanies Comedy Club Night

For a entertaining night out in the city, visit Zanies Comedy Night Club in Old Town. Zanies has been around for decades and has established itself as one of the seminal comedy clubs in the city. The laid-back atmosphere of the venue is perfect for visiting any time of the week with friends. Upcoming shows include The Female Funnies, a show centered on women comedians, and appearances by Kevin Bozeman, Adam Burke, Calvin Evans, and other talented comedians.  

Zanies Comedy Club, 1548 N Wells Street, Chicago, IL, USA, +1 312 337 4027

Thomas Masters Gallery

The Thomas Masters Gallery in Old Town is the perfect place for visitors to view art while enjoying the bustle of Chicago. At the Thomas Masters Gallery, over 30 artists are featured with pieces that range in medium, most of which consist of sculptures and paintings. Artists like Magdalena Abakanowicz, Tim Anderson, and Jean-Gilles Badaire have their art front and center, among a number of talented mixed-media artists. Past exhibitions have included Short Stories, a group art show featuring some of the TMG artists.

Thomas Masters Gallery, 245 W North Avenue, Chicago, IL, USA, +1 312 440 2322


By Alyssa Reyes