Gregory Stewart Tickets

Gregory Stewart is an emerging Chicago-based performer known for intimate, vocal-driven performances that weave R&B and soul with subtle jazz influences. From bustling club stages in Chicago to theatre productions, Gregory has built a diverse résumé that demonstrates versatility, warmth, and vocal depth. He has earned recognition through live engagements and a growing catalog of original work, including the 2025 self-released album Back In Love. Below you’ll find his biography, highlights from his discography, and details on upcoming shows, including his February 12, 2025 date at City Winery Chicago.

With roots in Chicago’s vibrant live-music scene, Gregory Stewart has developed a distinctive presence—characterized by intimate performances that invite listeners to lean in and experience raw, expressive storytelling through song.

For fans and new listeners alike, secure your seats to Gregory Stewart’s next performance and explore his journey from local club dates to more expansive stages. Follow his official social media for the latest updates and tour stops.

Album and single highlights, theatre work, and upcoming tour dates are listed below to help you plan your next live music experience with ease.