Freddie Jackson

Freddie Jackson

City Winery Chicago

Friday, September 25, 2026•7:30 PM

A defining voice of late ’80s urban contemporary, Jackson is celebrated for his rich, velvety tone and heartfelt ballads that continue to resonate with fans across generations. His performances glide effortlessly between tender slow jams and groove-driven classics, creating an intimate and emotionally charged live experience.

View event at tickets.citywinery.com

Rate your Overlook Events experience

About City Winery Chicago

1200 W Randolph St, Chicago, IL 60607

Open seasonally

+1 312-733-9463

More r&b/soul events

View all events

Weezer: The Gathering

Weezer: The Gathering

Sep 22·7:00 PM

WEEZER: The Gathering | Tue • Sep 22, 2026 • 7:00 PM | United Center, Chicago, IL

Mid America

Mid America

Sep 22·7:30 PM

All Time Low

All Time Low

Sep 22·6:30 PM

All Time Low | Tue • Sep 22, 2026 • 6:30 PM | The Salt Shed Outdoors (Fairgrounds), Chicago, IL