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Jill Andrews with Ali Sperry
City Winery LLC
Jill Andrews with Ali Sperry

Jill Andrews with Ali Sperry

07/16/2026
Thu 7:30 PM
Main Stage, City Winery Chicago - General Admission
1200 W Randolph St.
Chicago, IL 60607
United States
City Winery Chicago Presents Jill Andrews with Ali Sperry live on Thursday, July 16th at 7:30pm!

From her early days with The Everybodyfields to her acclaimed solo career and her collaboration Hush Kids, co founded with Nashville songwriter and producer Peter Groenwald, Andrews has spent nearly two decades crafting irresistibly melodic, genre bending music that continues to evolve. Her songs are anchored by emotional honesty and shaped by a wide range of influences, from Joni Mitchell, Diana Ross, and The Beatles to contemporary voices like Gregory Alan Isakov and St. Vincent.

Her music has become the soundtrack to some of television’s most beloved series, including Grey’s Anatomy, This Is Us, Nashville, and Wynonna Earp, for which she composed the theme song. Praised by American Songwriter for her beautifully crafted work and by Paste Magazine as one of today’s strongest female songwriters, Andrews delivers performances that are both intimate and powerful.

Join us for a special Thursday night of live music, wine, and dining in our warm and inviting Chicago venue. Reserve your seats now and experience Jill Andrews up close.

Nashville’s own Ali Sperry is a singer, songwriter, yoga teacher, transcendental meditationist and now… mother. Her journey to the joy of motherhood was especially hard fought and fraught with pain, grief, and spiritual exhaustion.

To those of us who have known and felt Ali’s clear eyed and incisive song writing and singing, it comes as no surprise that she does not shy away from any of those existential flash points on her new EP, When I Was a Mother and Other Songs

That Sperry, the living embodiment of “If you know you know,” even in Nashville’s thick matrix of low key master song crafters, manages to keep her lens steady when turned directly on the hardest nights of the soul, offers an odd kind of solace to the listener. Joy, Grief, Hope Trauma, are treated with the same anti-operatic clarity, and she sings her truths with the kind of crystalline under-singing that is her signature.

When I Was A Mother was produced by Sperry’s husband and life-collaborator Jamie Dick at Joy Carnival —- a studio built onto the back of their house during the pandemic. Even before the studio’s creation, Dick Manor was a social hub for East Nashville’s finest musicians, so it's not surprising that many turn up again on the EP, lured by the prospect of maybe cutting a tune, but almost certainly sharing a bottle and a gang of laughs… the kind of laid back effortless musical connection that feels like a bygone dream of a lost Nashville.

No one will accuse Sperry of being a furious careerist - it’s not in her genes - or her upbringing as the daughter of Iowa’s deep welled TM community. Her many cheerleaders do coax her out on the road though not as much as any of us would like — and when they do, she remembers how much she loves it, and why she does it. So rest assured, there will be tour dates coming in 2026.

In the meantime, you may have to come to Nashville and seek out this healer in her environs - on a yoga mat, or in a low lit bar, trading songs with her fellow song catchers and senders. She doesn’t dwell on the differences; we get our meditation and medicine where we can

-JT Nero(opens in a new tab)(opens in a new tab)


🍽️ We provide food and beverage service directly to your table in the venue. Or, for an expanded menu and more relaxed experience, arrive early and enjoy a meal in our restaurant before the show. When dining in the restaurant, reservations are encouraged and can be made via Resy starting one month before the show. View Our Concert Dining Menu.(opens in a new tab)


Reserve your preferred wine by filling out this form(opens in a new tab) and have a bottle waiting at your table when you arrive at your show. No more waiting for your first drink! We will save your wine preference and have a bottle at your table for all future shows. When you want to change your wine, come back to this form and update your preference.


2 Item Per Person Encouraged

🎶 While we do not require a two-item food or beverage minimum, we strongly encourage it. Most ticket revenue goes directly to the artist and production costs, so food and drink purchases help support the staff, service, and atmosphere that make these intimate shows possible.

The good news: we think you’ll love the food and wine just as much as the show.


🍷 Members get 48 hour early access to new shows, pay no ticket fees, and earn points to exchange for complimentary tickets. Vinofile Plus members also receive many wine benefits. Add a membership to your cart during checkout to start saving now. Already a member? Make sure you are signed in to access your benefits. Become a Vinofile Member and enjoy the benefits today.(opens in a new tab)

Jill Andrews with Ali Sperry
Main Stage, City Winery Chicago - General Admission
07/16/2026
Thu 7:30 PM
Main Stage, City Winery Chicago - General Admission
1200 W Randolph St.
Chicago, IL 60607
United States