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Rhett Miller with Reilly Downes & the Acid Cowboys
City Winery LLC
Rhett Miller with Reilly Downes & the Acid Cowboys

Rhett Miller with Reilly Downes & the Acid Cowboys

10/08/2026
Thu 7:30 PM
Main Stage, City Winery Chicago
1200 W. Randolph St
Chicago 60607
United States
City Winery Chicago Presents Rhett Miller with Reilly Downes & the Acid Cowboys live on Thursday, October 8th at (opens in a new tab)7:30 PM! (opens in a new tab)

Rhett Miller has spent more than thirty years proving that a great song is its own argument. As the frontman and primary songwriter of Old 97's, he helped define the alt-country movement before anyone had agreed on what to call it. The band's 1997 Elektra debut, Too Far to Care, remains a touchstone. Their 13th studio album, American Primitive, arrived on ATO Records in 2024. In 2025, the Old 97's received a Lifetime Achievement Award at the Americana Awards on the stage of Nashville's Ryman Auditorium.

The solo catalog runs eight albums deep, most recently A Lifetime of Riding by Night in 2025. Miller is also a writer whose essays and criticism have appeared in Rolling Stone, The Atlantic, McSweeney's, and Sports Illustrated, a podcaster with more than 200 episodes of Wheels Off: Conversations about Creativity, and a songwriting teacher at The New School whose annual Songwriting Is Magic retreat draws serious practitioners to the Catskills each year.

What it adds up to is a performer who brings genuine literary weight to the concert stage. The songs reward the kind of listening this room is built for.

An evening with one of Americana's most decorated voices, a carefully poured glass, and a Thursday in Chicago that earns its place on the calendar. Secure your seats.


🍽️ 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)

Video

Rhett Miller with Reilly Downes & the Acid Cowboys
Main Stage, City Winery Chicago
10/08/2026
Thu 7:30 PM
Main Stage, City Winery Chicago
1200 W. Randolph St
Chicago 60607
United States