Chicago Deep Cuts Fall 2026
Fall in Chicago has a way of turning the calendar into an argument for staying in the city instead of leaving it, and this stretch of the City Winery lineup makes that case well. Deep Cuts is where we put the shows some people already know and many haven't caught yet, the ones our programming team booked because they belong in a room this attentive, not because they need the introduction. This round has a hip hop tribute built like a small production, a comedy legend sharing a stage with a dance music icon, a songwriter with three decades of proof behind him, and a jazz record that pulls from three continents at once. None of it needs a hashtag to be worth planning around. It just needs a seat.
A Tribute to A Tribe Called Quest, presented by The J. Grant Experience
A Tribute to A Tribe Called Quest, presented by The J. Grant Experience
Monday, September 28 at 7:30 pm, City Winery Chicago
This is the seventh time J. Grant has staged this particular tribute at City Winery Chicago since it started back in 2021, and that's the detail worth sitting with. A show doesn't get invited back seven times because the room is empty. Grant leads a full live band built to recreate A Tribe Called Quest note for note, and layers in original Tribe music videos synced to the performance in real time, so the night lands somewhere between a concert and a screening. Whether The Low End Theory is a formative record for you or one you're discovering for the first time, this is a chance to hear it the way a room this attentive was built to play it.
It's Raining Queens, starring Martha Wash and Marsha Warfield
It's Raining Queens, starring Martha Wash and Marsha Warfield
Saturday, October 3 at 7:30 pm, City Winery Chicago
Martha Wash's voice is the reason The Weather Girls, Black Box, and C+C Music Factory sound the way they do on record, a two time Grammy nominee whose catalog shaped club floors and pop radio at the same time. Marsha Warfield built her name on timing, Emmy and NAACP Image Award nominated work on Night Court and continued credits on The Upshaws and 9-1-1 that have only sharpened her instinct for exactly where a laugh lives. Putting them on the same stage for one night, moving between music, comedy, and stories from careers that don't overlap but somehow rhyme, is the kind of pairing that doesn't repeat itself often.
Santiago Cruz: Sigo En Pie Tour
Santiago Cruz: Sigo En Pie Tour
Wednesday, October 7 at 7:30 pm, City Winery Chicago
Santiago Cruz has spent two decades building a catalog, ten albums and six Latin GRAMMY nominations deep, around songwriting that treats Latin pop, soul, and personal storytelling as one language rather than three. His latest record, Fragmentos, adds eleven new tracks to that body of work. In an intimate room built for close listening, that kind of songwriting reaches further than it does anywhere with a balcony.
Rhett Miller with Reilly Downes & the Acid Cowboys
Rhett Miller with Reilly Downes & the Acid Cowboys
Thursday, October 8 at 7:30 pm, City Winery Chicago
Rhett Miller has spent more than thirty years proving a great song is its own argument, first as the frontman of Old 97's and then as a solo artist eight albums into his own catalog. Old 97's picked up a Lifetime Achievement Award at the 2025 Americana Awards on the Ryman stage, which tells you where the genre landed on the question of Miller's influence. He also teaches songwriting at The New School and hosts a podcast built entirely around creative process, so a Thursday with him on stage comes from someone who thinks about the craft as much as he practices it. A glass of something well poured and a room built for listening does the rest.
Ami Taf Ra & Kamasi Washington present The Prophet & The Madman
Ami Taf Ra & Kamasi Washington present The Prophet & The Madman
Friday, November 13, doors at 6:00 pm, City Winery Chicago
Friday, November 13, doors at 9:30 pm, City Winery Chicago
Saturday, November 14, doors at 6:00 pm, City Winery Chicago
Saturday, November 14, doors at 9:30 pm, City Winery Chicago
Ami Taf Ra's debut record pulls from Moroccan Gnawa tradition, Arabic musical forms, gospel, and spiritual jazz, produced by Kamasi Washington and shaped by Kahlil Gibran's writing on duality and transformation. Washington, a Grammy winner and Emmy nominee in his own right, brings decades of work across jazz, soul, hip hop, and film scoring to the production. Two nights means two chances to hear a record built on cross cultural range performed by the people who built it, in a room small enough that none of that range gets lost.