Chef Norman Fenton leads a Latin American tasting menu at this Uptown spot. You might eat dishes like michelada oysters and huitlacoche ravioli alongside a taco omakase. Why Katrina and Jenner love it: “We’ve admired Chef Norm’s cooking since his schwa days. There’s a clarity and irreverence to his work that feels distinctly Chicago—deeply technical, but never self-serious. At Cariño, that sensibility comes through in food that is precise, expressive, and unmistakably personal.”

Come to this West Loop restaurant for Korean American food that’s best enjoyed with a group. Chef Andrew Lim’s barbecue menu pairs well with stews and rice dishes as well as the imported sojus and makgeolli. Why Katrina and Jenner love it: “Perilla is one of those restaurants where you immediately feel the strength of the team. The cooking is layered and exacting, yet incredibly comforting. It’s thoughtful food that doesn’t need to announce itself—it simply delivers.”

Tony Priolo and Ciro Longobardo spotlight rustic Italian food at this charming, verdant restaurant in River West. Pair your meal with a pick from the 400-bottle-strong all-Italian wine list. Why Katrina and Jenner love it: “Piccolo Sogno is a Chicago classic for a reason. It captures that effortless balance of refinement and ease, especially in the summer when the patio becomes one of the city’s most coveted tables. It’s timeless in a way few restaurants manage to be.”

“Top Chef” winner Joe Flamm nods to the Adriatic coast with this Italian and Croatian restaurant that’s just as popular as ever. Expect dishes like gnocchi with beef cheek and bucatini with rabbit. Why Katrina and Jenner love it: “We’ve long admired Joe—he embodies what it means to be a Chicago chef. Rose Mary feels both vibrant and grounded, blending technical precision with genuine hospitality. It’s buzzy, yes, but it’s also deeply rooted in craft.”

Seafood is the star at this popular restaurant that’s housed in a building inspired by a boat. Don’t miss the mixiote de mariscos en tomato or the various red snapper preparations. Why Katrina and Jenner love it: “El Barco is where we go when we want bold flavors and zero pretense. A michelada, a whole fish for the table—it’s celebratory, generous, and full of life. It reminds us that some of the best dining experiences are the most straightforward.”

Located inside the landmarked, 70,000-square-foot Gallery at the Historic Three Arts Club, this courtyard restaurant is worth visiting for the vibes alone. The brunch and dinner won’t disappoint either. Why Katrina and Jenner love it: “There are few places in Chicago as transportive for a midday escape. The architecture, the light, the energy—it’s romantic in the most understated way. It’s less about the meal and more about the atmosphere of being surrounded by beauty.”

This defining Chicago restaurant from chef Paul Kahan remains a favorite for a wine-focused meal where Midwestern and Mediterranean food comes together. Why Katrina and Jenner love it: “avec remains one of the city’s enduring benchmarks. The cooking is confident and unfussy, built on bold flavors and thoughtful simplicity. And the bacon-wrapped dates are truly iconic—a dish that helped define an era of dining in Chicago.”

This popular destination for some of the best sushi with a side of cold beers and hip-hop has also spawned a location in Nashville. Why Katrina and Jenner love it: “Sushi San has become part of our family’s rhythm. It’s lively but approachable, consistent without losing energy. The fact that it’s our son’s favorite restaurant makes it especially meaningful—it’s a place that works equally well for a weeknight dinner or a celebration.”

Night markets in Asia inform this lively restaurant in Bucktown. Chef Edward Kim blends Chicago ingredients with his Korean American upbringing in dishes like wok-fried Brussels sprouts with lamb pancetta and maple brown butter. Why Katrina and Jenner love it: “Mott Street delivers on every level—food, atmosphere, and energy. It’s one of those rare restaurants where the patio, the bar, and the kitchen all feel equally strong. That balance is hard to achieve, and they make it look effortless.”

Vietnamese food is in the spotlight at this romantic Oak Street destination from celebrated restaurateurs Rick Wahlstedt and Joe King. Chef Quoc Luong leads the kitchen, turning out dishes like Hanoi-style monkfish and shaking beef. W**hy Katrina and Jenner love it: “**Le Colonial is one of our most consistent touchstones. Whether it’s a spring afternoon near the open windows or a winter evening tucked into the moody bar, it offers a sense of refinement that feels enduring rather than trend-driven."

Seafood towers, fish and chips, and creative cocktails set the stage for a meal set in a massive, multi-level restaurant with views of the Chicago River. Why Katrina and Jenner love it: “At least once a summer, we find ourselves at RPM Seafood. Sitting along the river with a seafood tower and a spritz feels almost coastal—it’s a rare moment where Chicago feels like a destination resort. It’s celebratory in the best way.”

This date-night favorite does some of the best cocktails in town. Angle for a seat in the back patio decorated with string lights and pair your drinks with steak tartare, gnocchi, and more. Why Katrina and Jenner love it: “Ada Street will always hold a special place in our lives. Katrina helped open the restaurant alongside Michael Kornick, and it’s also where we were married. Intimate and quietly magical, it remains one of Chicago’s true hidden gems."