Make it a full night out at City Winery Chicago with dinner and a show in one destination. Enjoy chef driven cuisine, award winning City Winery wines, and handcrafted cocktails served directly to your table during live music, comedy shows, and special events. Prefer daytime plans? Join us for brunch and a show. Reserve your favorite wine in advance and we will have your bottle waiting at your table when you arrive, perfectly paired and ready to pour. We will also save your selection for future shows so every visit feels effortless.