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The Wells Street Art Festival is an annual event on the second weekend of June. It is located in Old Town's popular Wells Street corridor and attracts around 50,000 visitors yearly. The festival showcases talented artists from across the continent specializing in traditional painting, sculpture, artisan woodworking, metalsmithing, jewel crafts, digital arts, and more. Additionally, there is a dedicated performance stage where local musicians, performance artists, and cover/tribute bands entertain the crowd throughout the weekend. Moreover, at the corner of Wells Street and Evergreen Street is a children's play area where kids can participate in arts and crafts, watch a performance, or have fun. The festival also has over 20 food and drink vendors who sell a variety of tasty treats. Visitors can try something from all the excellent Old Town restaurants participating.

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.

The Hideout is not your typical bar; it's a place where everyone is welcome, regardless of whether they fit in. This prohibition-era bar may be small, but it's been a community space for independent music and performance in Chicago for over 25 years. On Saturdays, you can enjoy live music and dancing at The Hideout. It's a hub for music, art, performance, plays, poetry, rock, and rebellion. The bar is rooted in complex, hard-playing, creative artistic expression and intellectual freedom. It's more New Deal than New Age, and while it's not for everyone, it's for anyone who wants to experience something unique and authentic.

If you're searching for an exciting day trip near Chicago, look no further than Raging Waves Waterpark. With nine waterslides, a lazy river, a wave pool, and a giant sandbox, kids and adults alike will have a great time. Since opening to the public in 2008, Raging Waves has expanded to cover 58 acres, adding 15 more waterslides, 43 private cabanas, and 11 dining options. It's hard to believe that it all began with only 17 waterslides, a ¼ mile-long lazy river, a 350,000-gallon wave pool, a sand area, a leisure pool, and two restaurants.