31st Annual Retro on Roscoe Fest

CHICAGO, September 2026— Ever wish you could go back in time? Chicagoans looking for a blast from the past don’t need to look further than the 31 st Annual Retro on Roscoe festival. Get ready to time-travel at Retro on Roscoe, one of Chicago’s most beloved street festivals, happening Friday-Sunday September 18-20 in the charming Roscoe Village! This throwback extravaganza is packed with live music

Also in Lincoln Park, Lakeview & Wrigleyville

Gary Clark Jr. – Chicago, IL – 2026 TourFri, Sep 18, 2026 · 7:30pmThe Vic Theatre, Lincoln Park, Lakeview & WrigleyvilleOne Day Only

Annual Lakeview East Festival of the ArtsSeptember 19–20, 2026; Saturday 11 a.m.–7 p.m. (music, food and drink through 10 p.m.); Sunday 11 a.m.–7 p.m.North Broadway, Lincoln Park, Lakeview & Wrigleyville$5 suggested donationFree

More festivals this weekend

Riot Fest 2026 - SaturdaySat, Sep 19, 2026 · 11:00amDouglass Park, 1401 S Sacramento Dr., Pilsen, West Town & the West SideOne Day Only

Riot Fest 2026 - FridayFriday, September 18, 2026, 11:00 a.m.Douglass Park, North Lawndale, Pilsen, West Town & the West SideOne Day Only

Chicago Live at Navy PierSat, Sep 19 and Sun, Sep 20, 2026; Saturday 12–9 p.m., Sunday 12–6 p.m.Navy Pier, Downtown, the Loop & West LoopFREEOne Weekend Only

The 27th Anniversary Englewood Jazz FestivalSeptember 17–19, 2026; Thursday and Friday sets from 5:30 p.m. indoors, Saturday noon–6 p.m. outdoorsHamilton Park and Cultural Center, Hyde Park, Bronzeville & the South SideFreeOne Weekend Only

Fall Magnificent Mile Art FestivalSaturday, September 19 and Sunday, September 20, 2026, 10:00 AM–5:00 PM both days875 North Michigan Avenue plaza, Magnificent Mile, Downtown, the Loop & West LoopFree admissionOne Weekend Only

See the full ranked weekend board →