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Howie Day with Sean Skyler
City Winery LLC
Howie Day with Sean Skyler

Howie Day with Sean Skyler

04/22/2026
Wed 7:30 PM
Main Stage, City Winery Chicago
1200 W. Randolph St
Chicago 60607
United States
The sale has ended

SALE STARTS 10:00 AM 2/11

(opens in a new tab)(opens in a new tab)City Winery Chicago Presents Howie Day with Sean Skyler live on Wednesday, April 22nd at 7:30 PM!

(opens in a new tab)Howie Day’s emotionally resonant lyrics, inventive melodies, and heartfelt performances have earned him critical praise and a devoted global fanbase. Known for his energetic live shows, Day connects deeply with audiences through powerful songwriting, warm humor, and a tenor voice that can soar with beauty while carrying real emotional grit. With over a million records sold and two Top 10 hits, including the platinum single “Collide,” Howie Day returns to the stage in support of his studio album Lanterns. His performances blend intimacy and energy, often showcasing his innovative use of loop pedals that transform him into a dynamic one man band. A native of Bangor, Maine, Day began playing piano at age five and guitar at age twelve. By his mid teens, he was writing original music and performing across New England before becoming a staple of college coffeehouses nationwide. He independently wrote, financed, and released his debut album Australia, which won Best Debut Album at the 2001 Boston Music Awards and sold over 30,000 copies. The Boston Globe praised Day as “gorgeously seasoned, far beyond his years.” After signing with Epic Records, Day released Stop All the World Now, which was certified gold and produced the Top 10 singles “She Says” and “Collide.” He followed with Sound the Alarm, further expanding his emotionally rich sound and earning success with the single “Be There.” Following a move to New York City, Day released the Ceasefire EP on his own label before returning with Lanterns, recorded in Boston and featuring guest vocals from Aimee Mann. The album reflects a warm, layered musicality that highlights Day’s evolution as an artist. Now based in Seattle, Howie Day continues to expand his creative world through design, architecture, and visual arts while maintaining a close connection with fans both on stage and online. Experience an intimate evening of songs, stories, and unforgettable performances at City Winery Chicago


🍽️ 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 Minimum

🎶 Kindly note there is a 2 item per person food & beverage minimum in the concert venue. Food and beverages ordered in the restaurant also count towards the minimum.(opens in a new tab)


🍷 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)

Howie Day with Sean Skyler
Main Stage, City Winery Chicago
The sale has ended
04/22/2026
Wed 7:30 PM
Main Stage, City Winery Chicago
1200 W. Randolph St
Chicago 60607
United States