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Review: Chance the Rapper performs a love letter to Chicago

Chance the Rapper answered Chicago’s bat signal again Friday night. This time, though, being a crusader meant finding the right words for a city currently in the crosshairs of the Trump administration as the president ramps up immigration enforcement in the city.

“This is a crucial time and you live in one of the most important cities in the world, believe it,” Chance triumphantly declared to a riled-up crowd at Northerly Island. “Not just ‘cause of today, but historically,” he added. “I hope you know your history. I hope you take the time to look up what happens throughout history in Chicago any time [people] try and bully us. The power is in the hands of the people, the fight towards liberation continues and I’m so proud of y’all. I’m so proud to call myself a Chicagoan.”

While the West Chatham native has always worn his Chicago pride like a badge of honor, lately it’s been even more polished. Obvious sociopolitical circumstances aside, the feeling is an extension of the revelations heard on his latest project, “Star Line.” Released in August after a six-year gap, the album is one of Chance’s most progressive and expressive packages to date that finds the wordsmith and activist taking up both of his thrones with unbelievable conviction.

Teased ad nauseam for years, “Star Line” was unequivocally worth the wait. It’s a culmination of a journey that brought Chance back to his roots — both his Chicago origins (working with a strong assembly of Chicago’s hip-hop frontline), but also more globally the connections of the African diaspora and the Black experience. The album is named for the Black Star Line, an initiative founded by Jamaican activist Marcus Garvey as a means to liberate Black communities by transporting people and goods from the U.S. back to Africa. It was also inspired by Chance’s own travels to Jamaica and Ghana, particularly hosting the 2023 Star Line Festival with fellow Chicago emcee Vic Mensa.

There was another sense of pride in Chance’s work Friday night as many of the 17 songs from “Star Line” made up the bulk of the gripping 100-minute set, perfectly punctuated between the rapper’s other inked hits like “No Problem” and “Blessings.” Unlike those more uplifting bangers, buoyed by Chance’s longtime producer and keyboardist Peter CottonTale, the new material takes on a hardened seriousness that felt apropos for the times.

As Chance the Rapper performs Friday, song lyrics appear on a black screen behind him.

Candace Dane Chambers/Sun-Times

There was the mouthy rambler “Gun In Yo Purse,” advocating for women’s safety, and the quirky marijuana advocacy behind “Tree” that also speaks universally to inequities in Black entrepreneurship. As Chance dispersed the loaded barbs, each song’s lyrics flowed out like poetry on a black screen behind him, an overt measure to make sure people were paying attention and taking in the power of the rebellious words. He furthered that sentiment by dedicating the set in full to the late revolutionary Assata Shakur, who died last month, as well as political activist Angela Davis.

Chance also celebrated his hometown moment with the denizens of collaborators he worked with on the album, bringing out not only Mensa for the bold diatribe “Back to the Go,” but also 17-year-old local rising rapper BabyChiefDoIt for the “f— ICE” anthem “Drapetomania.”

Chance the Rapper performs with Do or Die at Huntington Bank Pavilion at Northerly Island on Friday.

Candace Dane Chambers/Sun-Times

Chance’s brother, Taylor Bennett, who opened the show with hits “Champagne Tears,” “Be Yourself” and “Roof Gone,” also had special guests like Englewood rapper Lil Moo and Chatham’s Adamn Killa. It’s Taylor’s first time touring with his sibling, and he thanked his “big brother” for the opportunity. He was followed by DJ Oreo, who took a moment to wish G Herbo a happy birthday and fellow openers Chicago rap trio Do Or Die, currently celebrating 30 years — all of it a bold display of Chicago’s hip-hop legacy, new and old.

But it was Chance’s guest Jamila Woods (described as his mentor and “one of the greatest writers and vocalists”) who came to the stage for the provocative piece “No More Old Men” that stood out most. The song laments the loss of Black men in Chicago due to violence and lack of health care, and it’s a track that Chance said he hopes will win “Song of the Year” at the Grammys; he and his team recently submitted “Star Line” and several of its songs to nine categories.

Chance the Rapper performs at Huntington Bank Pavilion at Northerly Island, Friday, Oct. 10, 2025.

Candace Dane Chambers/Sun-Times

As Chance has been sharing these takeaways on his national And We Back Tour, the title comes as a bit of a misnomer for anyone living in Chicago.

“People are like where you’ve been for six years, I heard you was gone … But for the most part I was here, I was in Chicago,” Chance explained, calling to mind the local initiatives over the past six years via his Social Works nonprofit, opening the Ramova and appearing at Lollapalooza (as he did in August to preview “Star Line”).

“Some of y’all probably ran into me before at McDonald’s or at Target or Skyzone or something. I hope to continue to see you all out there,” he added. While the rest of the world wants to call it a comeback, in Chicago, Chance is just doing what he’s always done – showing up.

Chance the Rapper’s Oct. 10 Concert at Huntington Bank Pavilion at Northerly Island

Star Side Intro

Ride

Tree

Work Out

Burn Ya Block

Drapetomania (with BabyChiefDoit)

Paranoia

Summer Friends

I Might Need Security

Back to the Go (with Vic Mensa)

Gun In Yo Purse

Pretty

Link Me in the Future

No More Old Men (with Jamila Woods)

No Problem

All Night

Blessings

Juke Jam

Letters

Speed of Light

Same Drugs

Speed of Love

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