Reggaeton Y2K

The high-energy throwback party Reggaetón Y2K is coming to Chicago, Illinois on Friday, September 25, 2026. This dance party celebrates the golden era of old-school Urbano music. The Music Hall will feature non-stop club anthems from the late 1999s and 2000s, spinning timeless hits from foundational icons like Daddy Yankee, Don Omar, Wisin & Yandel, and Ivy Queen.

More happening today in Downtown, the Loop & West Loop →

Chicago Gourmet 2026Through Sep 27, 2026Harris Theater Rooftop, Downtown, the Loop & West LoopOne Weekend Only

Martin Lawrence – Y’all Still Know What It Is! TourFri, Sep 25, 2026 · 8:00pmArie Crown Theater, Downtown, the Loop & West LoopOne Day Only

Ragamala: All-Night Indian Classical Music at World Music Festival ChicagoFriday, September 25, 2026, 6 p.m. through Saturday, September 26, 8 a.m.Chicago Cultural Center, Preston Bradley Hall, The Loop, Downtown, the Loop & West LoopFreeOne Weekend Only

Chicago White Sox vs. Colorado RockiesFriday–Sunday, September 25–27, 2026; Friday 6:40 p.m., Saturday 6:10 p.m., Sunday 2:10 p.m.Rate Field, Downtown, the Loop & West LoopOne Weekend Only

Also in Downtown, the Loop & West Loop

Sara Bareilles – Good Grief TourSun, Sep 27, 2026 · 8:00pmThe Chicago Theatre, The Loop, Downtown, the Loop & West LoopOne Day Only

Foster The People – Good Mourning Sunshine TourSat, Sep 26, 2026 · 8:00pmHuntington Bank Pavilion at Northerly Island, 1300 S. Linn White Drive, Downtown, the Loop & West LoopOne Day Only

Beatdown Sound System's Vibrations of Freedom at World Music Festival ChicagoSaturday, September 26, 2026, 1–7 p.m.Ping Tom Memorial Park, Chinatown, Downtown, the Loop & West LoopFREEOne Day Only

From Bomba to Salsa: Back to the Roots at World Music Festival ChicagoSunday, September 27, 2026, 2–4 p.m.Chicago Riverwalk, The Confluence, Downtown, the Loop & West LoopFREEOne Day Only

House Music Is Home at Navy PierSat, Sep 26, 2026Navy Pier, Downtown, the Loop & West LoopFree with RSVPOne Day Only

More live music this weekend →

Teddy Swims – The Ugly TourFri, Sep 25, 2026 · 7:00pmUnited Center, Near West Side, Pilsen, West Town & the West SideOne Day Only

Juanes: World TourSat, Sep 26, 2026 · 8:00pmRosemont Theatre, 5400 North River Road, Evanston & Oak ParkOne Day Only

Cold Waves XIV: Stabbing Westward, TR/ST, King Woman and More (18 and Over)Friday–Sunday, September 25–27, 2026; doors 6 p.m., show 7 p.m. each nightMetro, 3730 N. Clark St., Lincoln Park, Lakeview & Wrigleyville$55 advanceOne Weekend Only

Jeff Tweedy (solo acoustic) at FitzGerald'sFriday, September 25, 2026, 6:15 p.m.FitzGerald's Patio, Berwyn, Evanston & Oak ParkTickets via TicketWebOne Day Only

Sofi Tukker – Animal Talk TourFri, Sep 25, 2026 · 7:00pmHuntington Bank Pavilion at Northerly Island, 1300 S. Linn White Drive, Downtown, the Loop & West LoopOne Day Only

See the full ranked weekend board →