A kind of anti-rom com, that features a teacher Madina, daughter of a mixed marriage in Hyde Park, who moves to the suburbs, against her will, with her inattentive husband Sam. Madina has the spirit of an artist and wanted to be journalist in college but Sam and her parents encouraged her to take a safer, more traditional route. Madina encounters the confident, cool, and younger Caleb, a painter and delivery driver, while leaving the MCA and falls in lust. They cross lines and Madina imagines and lives the life she has always desired over the summer but there are consequences.

The genre of hip hop music known as Drill is an international phenomenon with robust scenes from NYC to the UK to Australia. But this low-fi, ominous sound scape and realist haunting lyrical descriptions of stark neighborhood conditions originates in name and style on the Southside of Chicago. This episodic documentary (or feature) tells the story of Drill's origination, and its common misunderstandings, with early adapters and originators of the style including Grammy-nominated rapper and writer King Louie and follows the Chicago story from Chief Keef to Lil Durk. Drill to Live is a story of hope about young people imagining different circumstances for themselves and their families and the troubled and brilliant city from which they come.

Rae Wolf has a desire to design streetwear in a male dominated space. She works in the more traditional and conservative world of women's fashion that is concerned with the bottom line. Rae likes the nightlife scene in Chicago and when she finds out her husband is cheating on her, she falls into a downward spiral of indulgence. Her craft, and son and mother, help to pull her out to have a chance to stay alive and create a life of that matters on her own terms.

Malik, the lead emcee, and his crew, prepare their biggest show to date, opening for The Wu-Tang Clan at The Metro. During the week, their final together unbeknownst to them, they prepare and wrestle with responsibilities, desire, and the prospect of following your dream.

A working class crew of die-hard Chicago Blackhawk fans create an ill-fated and desperate scheme to rob the team's star when he says in a post-game interview he'll be out of town for a family vacation. To the surprise of everyone, the star did not leave the city and chaos ensues in this bungling heist that articulates the class divisions in America, the modest hopes of the working class having and the sometime empty in the lives of the elite, in real and humorous ways.

A Chicago graffiti crew paints on the outside of The Modern Wing of the Art Institute a few weeks after opening and must go into hiding to avoid the police and a million dollar fine.