Celebrate the holiday season at City Winery Chicago, where festive concerts and seasonal entertainment come together with chef-crafted dining and award-winning wines. Located in The West Loop, our intimate, seated venue offers a memorable setting for holiday shows in Chicago, where guests can enjoy dinner before the show or food and wine served right to their seats during the performance. Beyond the holiday season, explore our full Chicago concert calendar, featuring live music from R&B and soul, rock, and jazz and blues to stand-up comedy, brunch events, and more. Whether you're planning a festive night out or looking for your next live performance, City Winery Chicago brings together live entertainment, food, and wine throughout the year.