The Time Out Chicago blog team

Ask any so-called expert what children need these days and you’ll get the usual answers: less screen time, more structure, consistent bedtime—and, inevitably, therapy. But according to Enrico Hufana, there’s something else kids need: the feeling of dropping into a quarter-pipe with nothing but a wooden board and the wings of their own confidence beneath them. Hufana is the founder of Little Ripper Skateboarding, a fast-growing skate school that began as a few lessons in a city park and has since evolved into a community hub—offering group and private classes, year-round programming and serving as an official Chicago Public Schools after-school provider. It’s not just a place to learn how to shred; it’s a space where kids build confidence, make friends and discover what they’re capable of. This year, they further expanded their reach, deepening their engagement with the community through grassroots activism and new after-school programming initiatives. It’s a vision that mirrors the organization’s mission: to bring skateboarding to kids of all ages, genders, racial and socioeconomic backgrounds—uplifting them through camaraderie, sportsmanship and community. In a city where access often depends on zip code or income, Little Ripper offers a space where everyone starts from the same place: one foot on the board, one push forward and a community ready to help them cruising. Photograph: Ricardo Adame From skater, to skate dad, to teacher Hufana’s love for skating began the...

Chicago’s Harry Potter Shop has officially gone full holiday mode, transforming into a snow globe-style wonderland that looks like it was dropped in by a particularly festive spell. But for one day this week, there’s an extra sweet reason to stop in. RECOMMENDED: See inside the much-anticipated new Harry Potter store now open in Chicago On Wednesday, December 4, the first 100 visitors will score a free Harry & Ron Sweater Cookie in celebration of National Cookie Day (one cookie per customer). But even the 101st visitor will have plenty of seasonal delights to enjoy. In addition to the sweater cookies, there will be Hot Butterbeer, authentic English mince pies, pumpkin tarts and macarons. Photograph: Courtesy of Harry Potter Shop Chicago Should anyone not have an appetite whilst shopping, there are still spells to fall under. The vibes are immaculate, for one; combining Harry Potter and the holidays is a recipe for cozy vibes that we could live in all year long. Take home a photo memento" step into a life-sized snow globe or grab a broomstick for a photo op that places you high above a snow-covered Hogwarts. The more adventurous can grab a map and embark on a Tree Trail scavenger hunt (complete it and earn a limited-edition “Holidays at Hogwarts” pin) or join one of the free 20-minute guided tours running through December 24, a nice way to geek out over actual props from the movies, décor and hidden Easter eggs for fans. Photograph: Courtesy of Harry Potter Shop Chicago ...

Mark your calendars—and prepare to warm up with some expertly crafted bourbon cocktails. On Sunday, December 4, Time Out Market Chicago will host Battle of the Bartenders, an epic cocktail showdown powered by Bulleit Bourbon. Some of Chicago’s top bars—including The Press Room, Friends of Friends and Kashmir—will go head-to-head for the chance to have their signature bourbon creation crowned number one. RECOMMENDED: The 24 best Chicago bars—the essential spots, ranked The best part? You decide the winner. Attendees can sample each bar’s cocktail, then cast their vote by dropping a gold coin (received at check-in along with drink tickets) into a ballot box of their favorite. The bartender and restaurant with the most votes will take home the coveted title of Top Bartender, plus a trophy, cash prize, a Time Out feature and, of course, bragging rights. Grab your friends and settle in for an afternoon of standout drinks, good vibes and maybe even the discovery of your next favorite cocktail. Battle of the Bartenders is a 21+ event. Tickets are $25 and can be purchased here.