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Photos: Rick Ross brings his Port of Miami 20th Anniversary Tour to Chicago

Rick Ross, the self-proclaimed B.O.A.T. (biggest of all time), sailed into Chicago last week as part of his Port of Miami 20th Anniversary Black-Tie Experience tour, featuring Chicago rapper Twista as special guest.

The Friday performance at Chicago Theatre coincided with the release of not just the hip-hop legend’s 2006 debut, “Port of Miami,” but also his 12th album, “Set In Stone.”

Appearing with the Renaissance Orchestra and the Sainted Trap Choir, Ross is the latest rapper to blend rap and orchestral music in a live performance; last year Jeezy brought his tour to Chicago in celebration of his debut album “Let’s Get It: Thug Motivation 101” and Nas marked the 30th anniversary of his debut album “Illmatic” with the Chicago Philharmonic at Ravinia.

Below, check out photos from Friday’s show at Chicago Theatre.

Rick Ross performs at the Chicago Theatre, Friday, July 17, 2026.

Tyler Pasciak LaRiviere/Sun-Times

Fans dance to Rick Ross as he performs performs at the Chicago Theatre, Friday, July 17, 2026.

Tyler Pasciak LaRiviere/Sun-Times

Rick Ross performs at the Chicago Theatre, Friday, July 17, 2026.

Tyler Pasciak LaRiviere/Sun-Times

Rick Ross performs at the Chicago Theatre, Friday, July 17, 2026.

Tyler Pasciak LaRiviere/Sun-Times

Rick Ross performs at the Chicago Theatre, Friday, July 17, 2026.

Tyler Pasciak LaRiviere/Sun-Times

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