The Resy Guide to Splurge-Worthy Dining in Chicago

The evening at Oriole begins inside a converted freight elevator that opens onto another world. First, drinks and opening bites in the lounge; then it’s on to chef Noah Sandoval’s two-Michelin-starred tasting menu, where seafood and seasonal ingredients keep you guessing. The signature detail is overhead, in a ceiling collage with hundreds of vintage concert posters, photographs, and mixed-media works above the open kitchen. Pro tip: Book the Kitchen Table for a closer view of the action, although the banquettes offer a view of the kitchen, too. Dinner will make a noticeable dent in your wallet, ranging from $390 to $474 per person, but it’s well worth it.

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Chef-owner Jake Potashnick decides what’s for dinner each morning, based on what arrives from local farmers, ranchers, fishermen, and dairy producers. Purple velvet banquettes and a gold-toned ceiling dress up the room, but the real show is in the open kitchen, where chefs prepare and plate a 25- to 30-course tasting menu. What lands in the kitchen that morning sets the course for dinner, so no two visits follow the same script. The tasting menu starts at around $225 per person.

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Originally from Busan, South Korea, chef Sangtae Park brings a traditional Edomae-style approach to a 16-course omakase. Carefully sourced seafood takes center stage, from delicate hirame and buttery otoro to sweet botan ebi and uni when available. The wood-wrapped dining room is as intimate as it gets: eight seats, two seatings a night (here’s how to get in). At $225 per person, be prepared to put the evening in chef Park’s hands.

At Galit, chef Zachary Engel gives Middle Eastern cooking his own spin, with local farmers helping shape what makes it on the plate. The falafel, carrots, and Iraqi kubbeh halab have earned permanent spots on the menu, and rightly so. So has the hummus crowned with tender, cinnamon-smoked brisket. Dinner is a four-course choose-your-own-adventure for $115 per person, before drinks. Ask about the wine pairing, and try to snag a seat overlooking the open kitchen. With its cozy interiors and deeply flavorful, spice-driven cooking, Galit makes a special dinner feel refreshingly unpretentious.

The three-Michelin-starred Smyth, led by husband-and-wife chefs John Shields and Karen Urie Shields, treats dinner as an exploration of what food can be. Fermentation, preservation and unusual combinations transform North American produce into something altogether less predictable. At $420 per person, Smyth is an indulgence; the $550 Chef’s Menu adds courses and a chance to meet the chefs. A $245 wine pairing of small-production, low-intervention wines carries the spirit of discovery into the glass.

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Under chef Carrie Nahabedian, French classics arrive with a few luxurious flourishes. Oysters come with seaweed cider vinegar and Chartreuse finger limes; foie gras with blueberry and chamomile; lacquered duck with summer cherries and beluga lentils. White tablecloths and broad windows overlooking Clark Street offer a respite from the city outside. Five- and eight-course tasting menus cost $170 and $235, respectively, with wine pairings available. For all its polish, Brindille still feels like a neighborhood favorite, where regulars are greeted by name.

This Indian-driven tasting menu takes a few delicious detours. Chicken makhani arrives with red pepper makhani (butter sauce), fenugreek black dairy dal, and garlic naan, while hen of the woods mushrooms get the pepper, black garlic, and truffle treatment. Crisp white tablecloths and blush booths dress up the industrial space. At $225 per person, it’s a splurge worth considering for anyone curious to see where chef-led Indian cooking can go.

Dimmi Dimmi brings Chicago attitude to Italian-American cooking. Case in point: chef Matt Eckfeld’s carpaccio gets a local spin—arriving like a deconstructed Italian beef sandwich, served hot or sweet with giardiniera, beef-jus aioli, Parmesan, and sesame sourdough on the side. The menu riffs on more of the classics—square-cut, tavern-style pizza; fresh pasta made daily; and housemade sausage. The space is new, but it already feels like a been-around-for-a-while spot, with roomy booths for groups and a bar stacked with amaro. A $75-100 dinner, best finished with a pour from the amaro list.

So you and yours have tickets to a show at the Cadillac Palace or James M. Nederlander Theatre downtown? A reservation at La Grande Boucherie will make the night feel like an occasion. The River North restaurant occupies a dramatic, two-level space with soaring ceilings, marble floors, and a pewter wraparound bar that’s ideal for a pre-show drink—or a night out on its own. The menu leans into French classics, from boeuf bourguignon and escargots to steak frites and broiled branzino. It’s indulgent, a little theatrical, and exactly the kind of place that makes dinner part of the main event.

Maxwells Trading’s appeal hasn’t waned three years in. Nestled in the Kinzie Corridor of the far West Loop, the kitchen blends Japanese and Chinese flavors with local ingredients. How local? A rooftop herb and vegetable garden fills the kitchen with seasonal produce, keeping the menu exciting and ever-changing. The dining room features soaring industrial ceilings, yet the ambiance remains warm and inviting thanks to rich wood accents and elegant design touches. Notable dishes include Japanese sweet potatoes served with Thai red curry, and the half-chicken a la brasa with yuca, aji verde, and ginger scallion salsa. Unless you get carried away with the dedicated martini list, it’s a manageable splurge at around $100 per person.

Brought to you by the Hogsalt team (Ciccio Mio, Armitage Alehouse, etc.), Trivoli Tavern is nestled into a charming cobblestone alley, giving off intimate speakeasy vibes perfect for cozy date nights or lively group gatherings. Kick off your evening with a strong cocktail and a round of oysters before diving into their hand-rolled pasta offerings. (Do try the mafaldine coated in black truffle oil and melted pecorino.) And don’t leave without the sticky toffee date cake—a celebratory dessert if there ever was, topped with brown butter ice cream and a toffee crumble. Expect to spend upwards of $100 per person, more if you’re tempted by the premium cuts—which, at Trivoli, is easy to do.

At this perennially packed Italian favorite, sharing is encouraged and chef Sarah Grueneberg’s handmade pastas take center stage. Highlights include the pesto gnocchetti tossed in basil pesto, housemade ricotta, and a sprinkle of Sardinian pecorino; and the cacio whey pepe, a bowl of fusilloni swirled in rich pecorino medoro, lemon ricotta, and seasoned with a four-peppercorn blend. The ambiance walks the line between upscale elegance and inviting warmth, matched by a truly stellar wine list–perfect for a celebratory dinner, date night, or a standout meal with friends. Plan on spending around $75 to $100 per person for a family-style dinner.

Bavette’s is a dimly lit, chic-yet-unpretentious steakhouse with a penchant for French cuisine, making it a dreamy destination for a romantic night out with a date or friends. The speakeasy atmosphere comes together with glowing chandeliers and burgundy leather booths along the walls. Opt for a 16-ounce, 42-day dry-aged, bone-in New York Strip drenched in béarnaise and sprinkled with steak salt, or roasted bone marrow served with caramelized red onion jam and parsley salad. The juicy double wagyu cheeseburger is also a solid choice, topped with pickles, onions, Dijon, and a side of pomme frites, naturally. Come hungry, order the steak, say yes to another glass of wine, and plan on $100–150 per person.