Brandon begrudgingly puts on a front to help Jerrika land a new client. Reg must answer to the leadership of the 63rd St. Mob. Ronnie reels from devastating news and makes a deal with an inmate. Emmett adjusts to his new living situation and starts another side hustle with Amir. Kevin is forced to make a difficult decision. New Detective Toussaint investigates a South Side home invasion.
Brandon stresses over The After Taste Food Competition and makes a deal with Emmett, while an accident at Sonny’s threatens Emmett’s job. Kevin, Jake and Papa cause mayhem on picture day at school. Ronnie adjusts to a new life he didn’t expect. Reg gets called on the carpet by Douda and a revelation comes to light.
Brandon and Emmett come together for some Chicago summertime fun on one of the hottest days of the year. Kevin deals with a death in the family. Ronnie reconnects with Rafiq and gets some helpful advice. Toussaint and Cruz make a major move on the home invasion case. Reg and Douda form a plan to fix the gang’s problem.
Emmett's past threatens his new marriage. Kiesha wrestles with a decision that will affect the life of her unborn child. A run in with law enforcement leaves Kevin, Jake and Papa reeling. Douda tries to walk the line between gangster and mayor. Tiff and Dom go into business together. Marcus petitions to bring the Olympics to Chicago.
Emmett attempts to win Tiff back. Kiesha looks to start a new chapter for her and her son. Kevin takes his passion to a new level. Jake tries out for the basketball team. Papa’s announcement at the school pep rally quickly takes a turn for the worse. Jada hits a roadblock in her relationship with Suede. Trig takes a major step while continuing his efforts to protect the community. Douda and an old face return to visit Tracy.
Emmett’s co-parenting struggles lead him to some questionable advice. Jake reconnects with someone from his past. Kiesha’s college housing plans go awry. Tiff’s relationship with Rob heats up. Kevin sets his sights on a new love interest while navigating his gaming club. Papa struggles with being cancelled. Jada reveals a secret to Suede. Trig considers a new role in the community.
Emmett and Kiesha bond over being single parents. A discovery prompts Jada to confront Suede. Trig and Jake enjoy Christmas morning with their family. Papa tries and fails to apologize. Tiff and Rob’s relationship grows stronger after a holiday mishap. Douda delivers a Christmas miracle for the community.
A welcome new development in Douda’s life is complicated by Roselyn. The strains of their busy lives wear on Emmett and Kiesha. Tiff and Rob make strides with their business. Papa introduces Kenya to the crew, while Maisha questions Jemma’s dedication. The men of The Chi turn to each other for support.
Emmett and Darnell's father-son time is interrupted by a revelation; Papa is wooed by Pastor Ezekiel, causing tension with his mother; Alicia offers Shaad an opportunity.
Emmett looks to a new partnership as a solution to all his problems; Victor is haunted by his past mistakes; Papa makes a big decision; devastating news sends Kiesha reeling.
Douda's birthday sparks emotions; shocking news brings new problems for Emmett and Kiesha; Damien makes a surprising discovery while Alonzo takes a bold step.
Jake does his best to distract a restless Victor; Alicia makes a deal and issues a warning; Papa takes centre stage while Britney confides in Maisha and Jemma.
Rob and Tiff host Thanksgiving, but not without interference from Alicia. Meanwhile, Douda seeks revenge on all who've done him wrong, leaving everyone in the Chi on edge. Sensing the tension, Roselyn stresses over Douda's safety.
Thanksgiving marks a time for reunions and revelations as families gather to celebrate.
Kevin, Papa, and Jake give advice about handling questions from adults.
Kevin, Papa, and Jake talk about going to school on the South Side.
Kevin, Papa, and Jake talk about what they want to do when they grow up.
Kevin, Papa, and Jake discuss the pros and cons of living outside the law on the South Side.