Rosa's Lounge

City Winery is a 300-capacity All Ages venue in Chicago, Illinois welcoming All Song Types. City Winery strives to deliver the highest-end combined culinary and cultural experience to our customers who are passionate in sharing wine, music, and culinary arts. . Programming includes Acoustic, Americana, Bluegrass, Blues, Folk. Booking is handled by email, so keep the inquiry concise and specific. The house sound setup is not confirmed, so technical requirements need direct agreement. Clarify the stage setup, schedule, promotion expectations, compensation, and guest policy before travel is locked. The practical work is ordinary; doing it well is what gives the night room to become memorable.

Untitled Supper Club is a large River North supper club with recurring live bands and professional entertainment production. The musical lane includes Jazz, Soul, R&B, Funk, Cover Bands. Its professional setting is especially well suited to — dedicated supper-club stage hosting live bands and jazz in a professional nightlife setting. The social setting favors musicians who can hold attention without overpowering conversation or service. The value of the booking comes from matching the act closely to the venue’s established audience experience.

Andy’s Jazz Club is a River North music room presenting multiple live jazz sets every night alongside a full restaurant and bar. The venue balances serious listening with a polished dining experience, making jazz trios, quartets, vocalists, piano-led groups, blues, soul-jazz, standards, and small horn ensembles especially natural fits. For musicians, the frequent nightly schedule rewards professionalism, tight arrangements, and consistent sound rather than oversized production. The audience is seated close to the performers and generally comes expecting live jazz, so subtle dynamics and musicianship register clearly. A compact ensemble works best, and strong stage communication matters because the room is intimate. Andy’s is a strong Chicago target for experienced jazz players and touring small groups looking for a centrally located room with multiple nightly sets, an established audience, and a professional music-and-dining format.