Best of the City: The nine best things Time Out Chicago editors saw, ate and visited in 2025

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. This year, they further expanded their reach, deepening their engagement with the community through grassroots activism and new after-school programming initiatives. 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.

It’s safe to say that 2025 was the year of the all-day cafe, and Metric Coffee’s ultra-popular Milli was its breakout star. The Avondale cafe and roastery has made headlines since its fall debut for its cozy, retro-inspired design (courtesy of Metric co-founder Darko Arandjelovic), excellent coffee and zero-proof sips, plus its next-level pastry program, led by pastry chef and Obelix alum Lou Turner. Melt-in-your-mouth cookies, perfectly flaky croissants, and masterfully crafted eclairs are our early favorites. The team plans to expand its hours and menu to introduce natural wine, beer and kombucha on tap, as well as full-fledged breakfast, lunch and dinner offerings.

There may be no greater champion of Chicago’s South Side than Theaster Gates. For over a decade, he has transformed long-neglected buildings into hubs of art, learning and community—most famously the Stony Island Arts Bank—while preserving and celebrating the cultural materials that shape the city’s identity, from Frankie Knuckles’ record library to archives and objects tied to Black history and power. It feels fitting, then, that Gates’s first major hometown solo exhibition arrived in one of Chicago’s most uncertain and demanding years. “Unto Thee,” now on view at the University of Chicago’s Smart Museum of Art, reflects Gates’s enduring belief that art can bridge divides, restore dignity and move communities forward. The self-described “keeper of objects” presents collections of glass lantern slides, pews originally crafted for Bond Chapel and other historical materials in dialogue with his multidisciplinary work. Together, they form a kind of visual hymn—an ode to Chicago, its stories and the people who sustain its creative spirit.

Lincoln Park’s newest dining darling, Dimmi Dimmi, made a major splash this year. Just as popular as notoriously tough-to-reserve Armitage Alehouse down the street, you might need to sacrifice your firstborn for a dinner res—but at least you’ll have leftovers. Chef Matt Eckfeld (Carbone, Urbanbelly) gave us mouthwatering mozzarella sticks, decadent stuffed shells and a paper-thin tavern-style pizza that gives Vito & Nick's a run for its money. In a review published shortly after the restaurant opened this summer, we were curious to see how long the fanfare would ensue. Today, we can confidently say that Dimmi Dimmi undoubtedly lives up to the hype.

When Pitchfork Music Festival announced its abrupt sunset at the start of 2025, Chicago’s music scene collectively wondered how cofounder Mike Reed would fill the newly opened sonic void. As it turns out, Reed had an ace up his sleeve: Sound & Gravity, a five-day marathon featuring more than 50 performances spread across six venues throughout Bricktown and Avondale.

Designed to get people talking—and walking—between shows, the festival made it easy to stroll from Melkbelly’s shredded garage rock set at Guild Row to Kim Gordon’s Body/Head performance at Beat Kitchen, catching up with friends along the way. In keeping with that community-first spirit, one stage was curated by Electrical Audio, the studio founded by the late Steve Albini, and featured artists central to the studio’s legacy and Albini’s unmistakable taste. Sound & Gravity proved that music festivals don’t need corporate wallpaper or faceless sponsors to make an impact; they can be fresh, thrilling and—most importantly—rooted in the art and the community that keeps it alive.

Gus’ Sip & Dip doesn’t take reservations, but trust us, it’s worth the wait. The dimly lit River North watering hole from Lettuce Entertain You is located in the former Hub 51 space. Notably, all mixed drinks are priced at $12 (!), which, in this economy, is practically unheard of downtown. And they don’t sacrifice quality for quantity. Drinks like the gin-based Breakfast Martini (orange liqueur, Earl Grey, marmalade and honey toast) and Naked and Famous (mezcal, Aperol, yellow chartreuse and lime) are stiff and pair well with bites like the Wagyu beef dip sandwich and black truffle grilled cheese. It’s not easy to break out in the city’s dense bar scene, but with Lettuce’s legacy and beverage director Kevin Beary (Three Dots and a Dash) at the helm, this elevated tavern is the year’s best new bar.

If you wandered past the Music Box Theatre earlier this year, you may have noticed a new neighbor of the eerier persuasion. Terror Vision Records and Video—a pop-up shop and fully functioning video rental store devoted to all things horror—opened in early 2025. The brainchild of two notable Chicagoans, Ryan Graveface (of Graveface Records and Curiosities) and filmmaker Joe Swanberg, the shop carried VHS tapes, vinyl, Blu-rays and just about any spooky artifact an analog-obsessed collector could dream up.

For a time, it was arguably the only place in Chicago where you could pick up a Blu-ray of Sledgehammer and the Cabin Fever soundtrack LP in the same transaction. Terror Vision wrapped up its Southport Avenue run after Halloween, but the experiment didn’t end there. Two new pop-up rental locations have since opened: one in a Bucktown storefront, the other inside Ravenswood’s historic Davis Theater. Members can browse a deep and wonderfully strange library, rent movies without fear of late fees and revel in the tactile joy of media that still comes in a box you can hold.

Perhaps no other dining pop-up had as big a boom this year as Morning Jay’s. The breakfast-centric series from Justen Lambert and Nate Crawford began as a series of “cozy cafes,” intimate pop-up meals inside their home. Since then, they’ve hosted pop-ups at Side Practice Coffee, Reprise Coffee Roasters and Ford’s Cars & Coffee event. Their quick virality can be attributed to a few factors: Nate’s food photography and branding chops, Justen’s baking prowess, and a damn-good breakfast lineup. Morning Jay’s rotating menu has featured standouts like ube-banana pancakes, loaded tater tots with house-made chorizo, strawberry-golden sugar scones and a drool-worthy gochujang bacon focaccia sandwich. With more pop-ups on the horizon and plans to expand the brand, we can't wait to see where Morning Jay’s goes in 2026.

Ever miss the grade-school thrill of forcing a captive audience to listen while you talked about your favorite thing in the entire world? Show & Tell for Grown-Ups has you covered. Once a month, comedians, storytellers and enthusiastic everyday hobbyists gather at rotating venues—Lincoln Lodge, Heritage Coffee & Bikes, Snakes & Lattes—to present five-minute deep dives into their most cherished, quirky or oddly specific passions. Afterward, the audience gets a brief Q&A to poke, prod and learn even more. Past presentations have tackled everything from “The Miracle of Salmon” to “The Best Collection of American Girl Dolls” to the existential question “What’s up with crickets?” Best of all, anyone can submit a topic, making room for ordinary Chicagoans with extraordinary fascinations. Think of it as falling down a Reddit rabbit hole—only live, communal and infinitely more charming.