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City Winery is a unique venue that offers live entertainment and a wide selection of wine in a warm and welcoming atmosphere. With a working winery on site, guests can enjoy up to 18 varieties of wine while being entertained. The venue can accommodate up to 300 guests, and each location offers a distinctive culinary and cultural experience for wine enthusiasts. City Winery has expanded to provide intimate concerts, food and wine seminars, private event spaces, upscale dining, and a fully functioning winery. Experience the charm of wine country with modern comfort and convenience in an urban setting. The performance venues are equipped with state-of-the-art acoustics provided by Meyer Sound. Before the concert, you can visit the tasting room to try a flight of wines. After the show, stop by the bar for more drinks. City Winery offers a range of functional spaces that can host a memorable night out for two or an unforgettable private event. There is something for everyone at City Winery, whether it's discovering new wines while enjoying an intimate concert or celebrating your wedding in the wine garden followed by an epic party.

If you're a fan of Shakespeare, you should attend the Chicago Shakespeare Theater on Navy Pier. This professional theater company was founded in 1986 by Barbara Gaines and is the third largest in the Midwest. They produce works from the Shakespeare canon and other theatrical performances, with over six hundred performances annually at the Courtyard Theater and the Upstairs space. The theater has won numerous awards, including 36 Joseph Jefferson Awards, three Laurence Olivier Awards, and a Regional Theatre Tony Award. The theater also has a family series for younger audiences and special student pricing.

Chicago's Best Standup Comedy is back and better than ever before. The comedy club has assembled an outstanding lineup of comedians you won't find anywhere else in the city. From the biggest names in the business to local talent, there's something for everyone's taste and style of comedy. Since 1979, the world-renowned Laugh Factory has entertained audiences and is recognized as the "#1 comedy club in the country" by USA Today. The Laugh Factory has brought laughter to millions of people around the world. It's a place where locals and tourists can go for an evening of guaranteed smiles and where comedy's most prominent stars visit to feel like they're part of comedy history. With features like a comedy magazine and a historic stage, the Laugh Factory has helped launch the careers of countless comedians and continues to nurture up-and-coming talent.

Attention food enthusiasts in Chicago! Have you ever considered exploring the city's food, history, and architecture all in one walking food adventure? If so, Tastebud Tours is the perfect choice for you. Get ready to embark on a delicious journey through specialty dessert shops, famous deep-dish pizza joints, Chicago-style hot dog stands, and unique ethnic eateries. Tastebud Food Tours strives to provide its guests with a world-class food tour experience of exceptional value. Their tour guides are the secret ingredient to their success, and they take pride in their spirit of loyalty, enthusiasm, and dedication.