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City Winery tickets & upcoming events

Looking for a cozy yet lively spot to catch some incredible live music and enjoy great wine? City Winery in Chicago is exactly that place. Situated just a stone’s throw from the iconic Sears Tower, it’s super easy to get to, just hop off the Brown Line at Washington/Wells and walk a couple of blocks west. The vibe here is warm and inviting, perfect whether you’re coming with friends, family, or even flying solo. They really do a good job blending local culture with their offerings, think pairing wines with bites from local chefs during special culinary events that make your taste buds dance. Plus, they’re big on community too, supporting local sustainability initiatives and making sure everyone feels welcome. The staff knows their stuff on wine pairings and are happy to recommend something you might not have tried otherwise. Got a favorite artist like Joshua Radin or Red Wanting Blue? You’ll find seats that suit you, whether you want front row or a cozy VIP section. And if you’re worried about accessibility or switching seats last minute, the interactive seating chart on their website has got you covered. Honestly, it’s a fantastic spot to spend an evening, whether you’re craving a relaxed night out or a memorable concert experience. Trust me, once you’re there, it’s hard not to want to come back.

Parking & Directions for City Winery - Chicago

Address :
1200 W. Randolph St., Chicago, IL
60607, US

Parking:
1. City Winery Lot - 0.1 miles, $20
2. Union Station Garage - 0.3 miles, $10
3. 500 W. Madison St. Garage - 0.4 miles, $15
4. 400 S. Wells St. Lot - 0.5 miles, $12
5. Millennium Park Garage - 0.6 miles, $25

City Winery concerts - 2026 event schedule highlights in Chicago

City Winery - Chicago is a vibrant live music and entertainment venue located in the heart of Chicago, offering a diverse lineup of performances spanning genres from jazz and soul to pop and tribute acts. Throughout 2026 and early 2027, guests can enjoy an exciting array of events, including concerts by renowned artists such as Musiq Soulchild, Chris Botti, Marcus Miller, and Freddie Jackson. Notable performances include Musiq Soulchild’s multiple shows in september and october, and the highly anticipated Halloween-themed Michael Jackson's Thriller Live: A Halloween Special on October 29, 2026. The venue also hosts special themed brunches like the Soul Brunch: Annual Motown Spectacular on September 26, 2026, and the Beatles Brunch with Phil Angotti on September 20, 2026. Fans of jazz can look forward to performances by Chris Botti in October, while R&B fans can catch Lyfe Jennings in early September. The lineup features tribute bands such as Zoso - Led Zeppelin Tribute Band on October 25, 2026, and Fleetwood Mac’s The Seven Wonders on September 22, 2026. Additionally, comedy and spoken word performances like D.L. Hughley's stand-up shows and Seasoned Dialogue with Lisa Marie Lovett add to the venue’s versatile entertainment calendar. With performances scheduled nearly every week, City Winery - Chicago offers an unforgettable experience for music lovers, comedy enthusiasts, and cultural explorers alike, making it a premier destination for live entertainment in the city.