Chicago-based Sidewalk Chalk is a hive of ingenuity and aspiration. From keys, drums, horns and bass to an emcee, powerful female vocals and a tap dancer, this eight-member crew thrums with talent. Despite the layers and complexities, the members of Chalk share a common passion — to transcend the norm, the expected, the known — resulting in a fluid sound that is equal parts jazz, soul, hip hop and funk.

When EW asks the band what fuels this drive, Rico Sisney, the band’s emcee, replies: “I think it stems from the music. Individually we want to stretch and do new stuff. We want to take risks.”

And so the group’s 2015 album, Shoulder Season, features live performances of all-new songs, a nod to the audience’s role in their music and to improvisation’s influence in both songwriting and performing.

“I love the spontaneity,” Sisney continues. “We’re playing music that we really like and we’re trying to do things that will excite each other. I think the audience experiences and feels that, and I think that’s the biggest thing about our shows.”

Shoulder Season is their third album — and perhaps their most experimental — built upon the solid foundation of their debut, Corner Store, and their popular follow-up, Leaves. Aptly, this new album explores transitions — “the idea of being between two things,” Sisney explains. “Whether that’s between two sides of an argument or between two places historically or emotionally or two ideas within yourself.”

Who better to traverse such shifts and evolutions than a family of artists inspiring each other?

Sidewalk Chalk plays 8 pm Thursday, Oct. 22, at WOW Hall; $10 adv., $15 door.