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Playful Italian at the Wit, million-dollar views and $23 burgers on Trump's Terrace, and fussed-up brunch at Jam in Ukrainian Village

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The name is Italian for "crazy food," but I can't say there's anything inherently kooky about what's being served at Cibo Matto, the third and most anticipated of the new restaurants at the Wit Hotel. But compared to State and Lake, its relatively safe and boring downstairs neighbor, it is pretty remarkable—especially considering both are operated by the 16-unit empire Concentrics Restaurants. In fact, Cibo Matto could pass as Spiaggia's more playful, easygoing younger sibling. What does an Atlanta-based operator know about how to play restaurant in Chicago? For one thing, it enlisted chef Todd Stein, who racked up a lot of goodwill in his time at MK and makes an impressive departure from the contemporary American he focused on there, shifting to irreverent upscale Italian with a slight preference for sea creatures.

It's on the pricey side, with most antipasti and pastas ranging from $11 to $16 and entrees hovering around $30. So it helps that many of these dishes have compelling stories a server can sell: the grilled octopus gets simmered with a wine cork; the bone-in halibut fillet is custom cut by the purveyor to maximize flavor; mascarpone creamed spinach was repeatedly and unironically touted by one waiter as "off tha hook." In most cases the plates lived up to their pitches—that octopus, abetted by salsa verde and pickled pearl onions, might have been the most tender and perfectly cooked cephalopod I've preyed upon in recent memory, and the grilled halibut yielded all the promised flavor. The dull, dairy-doused spinach, paired with braised short ribs, failed to live up to its revolutionary promise.

What's more, for every marquee item that delivered, I probably enjoyed two unheralded but quietly excellent dishes, beginning with a bowl of peppery bucatini carbonara with cured tomatoes, chiles, and a brilliant orb of duck yolk mixed in at the table—one of the greatest riffs on the classic I've ever had. The spaghetti alla chittara was every bit as good in terms of the quality of the noodles, just undercut by slightly overcooked shrimp. Crispy sweetbreads augmented with cross sections of fried lemon chips, juicy roast chicken exuding gusts of lavender, roasted chicken livers on polenta crisscrossed by slices of crispy duck "bacon," salty but rich quivering roasted scallops on celery root puree, and crispy seared trout—all collectively redeemed the loud, crowded atmosphere. —Mike Sula

Million-dollar views of the Wrigley Building and the Chicago River are the main reason to check out The Terrace at Trump—but not the only one. The thoughtfully designed space, accented by burbling fountains and stands of prairie grass, offers a welcome variety of seating options, among them comfy couches, large round tables, cocktail tables for couples, a communal table, and a small bar. And thanks to a no-standing-room policy, the place doesn't get packed. Sure, you'll pay $10 for a beer, $17 for a nautically themed cocktail, and $12-$25 for a "rosé is the new black" sparkler or glass of wine, but drink prices include tax, and the Skipper—reminiscent of a mojito, with coconut—was refreshing, even if my glass of Gran Sarao cava was almost flat. (When I told the attentive server, he replaced it.)

Frank Brunacci, executive chef of Sixteen, oversees the compact menu, which is predictably sophisticated and expensive. A bowl of al dente summer orecchiette turned out to be both enjoyable and a decent deal at $15, laced with lots of mild lump crab meat, sweet corn kernels, diced bacon, and spinach. But at $14 the duo of small crispy spring rolls—containing a few morsels of duck leg and bedded on bland carrot coulis—disappointed. I had trouble imagining what could make even a prime sirloin burger worth $23; still, the half pounder arrived rare as ordered, on a soft brioche bun that didn't quite hold up, topped with a nice balance of caramelized onions, farmhouse cheddar, and baby greens. It also came with good waffle-cut truffle fries, which are $7 a la carte. Judging by a dull milk chocolate hazelnut bar, I'd say skip the $10 desserts, and definitely forgo the $5 coffee.

The downside of controlled access is that the wait for seating outdoors can stretch into hours. The way to avoid it: come around 2:30, when the doors open (the kitchen opens at 3), and relax over a late lunch. No one made us feel rushed, despite the line by the time we left at 5 PM. —Anne Spiselman

The fussed-up Ukrainian Village brunch spot Jam, which launched stealthily in mid-July in the tight, airless Damen Avenue space where Dodo expired, is a radically different animal from owner Jerry Suqi's nearby Chickpea. This time it's not Suqi's Palestinian mama in the kitchen but Jeffrey Mauro, formerly of Trotter's and North Pond (he also teamed with Suqi on the ill-fated La Pomme Rouge). Mauro, along with sous chef Mike Noll (Schwa), commands the open-air kitchen while Suqi prowls and expedites in the L-shaped dining area; and while the place is perfectly welcoming, it's the antithesis of Chickpea, with its kitchen-table vibe.

Early notices touted Mauro's sous vide malt custard French toast and eggy plates fashionably loaded with pork cheeks and belly, which gave me the impression that this was going to be the sort of brunching meant for blanketing uneasy stomachs and pounding heads. And indeed Mauro's egg sandwich, a French roll with slabs of meaty braised pork cheek covered in a lava flow of egg yolk, has a restorative quality, marred only by a cloying sweet-and-sour peach ketchup—a rare case of sugar failing to help the medicine go down.

Buckwheat crepes stuffed with braised lamb are plated more successfully, with perfect spheres of Asian pear, but biscuits and gravy with satisfying chunks of rough-cut cotechhino sausage are nearly undone by a gray shiitake gravy that looks far less appetizing than it actually is. Some plates, particularly those categorized as lunch, are downright dainty and overcomposed, like the octopus: a few tentacles, a tuft of frisee, and a radial arrangement of pink grapefruit sections alternately dabbed with yellow ginger icing and crenellated with coins of dehydrated chorizo chips.

Meals start with imaginative amuses, such as intensely anise-y fennel sugar-lemon custard doughnut holes, which you can wash down with Metropolis coffee or a juice du jour. All slate and mirrors to maximize limited space, the cash-only operation is hot and poorly ventilated—which doesn't seem to deter the weekend mobs currently helping the restaurant live up to its name. —Mike Sula

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