The halibut is poached in a liquid that's made in part with Paul McGee's Bloody Mary mix. Credit: Andrea Bauer

It’s not difficult to imagine the old days of the Chicago Athletic Association, when jowly titans of industry circled each other like rutting pronghorns, slugging whiskey and lobbing medicine balls in their sweat-damp towels. The recent restoration of Henry Ives Cobb’s 122-year-old Venetian Gothic edifice is so remarkable that if you could only shut out the chatter of the new Michigan Avenue hotel’s casually dressed guests you might hear the ghosts of the fusty old patriarchy harrumphing at the sudden presence of the fair sex in their midst. That’s especially true of its primary restaurant, Cherry Circle Room, a majestic dining space where not even a soundtrack of the Stooges and Nick Cave can burn off the mist of louche exclusivity. The enigmatic grandeur is further enhanced by the framed silk banners of imaginary secret societies that hang on the walls and the arcane symbols painted on the serviceware. The bar, the room’s most prominent feature, wraps around nearly half its outer edge. Behind it bartenders scale ladders to reach bottles of spirits situated next to incongruous bric-a-brac like vintage megaphones, astronaut helmets, and statuary of reposing sheep.

This, together with two other dining areas in the hotel (the Milk Room and the Game Room), is the most physically impressive project to date from Land & Sea Dept. (The rooftop bar, Cindy’s, is operated separately.) Paul McGee of L&S’s Lost Lake has been enlisted to handle the spirits; Andrew Algren, formerly of Alinea, is the sommelier; and Peter Coenen, a veteran of Boka and the Gage, helms the kitchen.

Last week I was lamenting the poorly executed “American classics” at nearby Remington’s, and like the offerings there, the menu at Cherry Circle Room doesn’t stray far from the comfortably familiar—there are steaks, a chop, chicken, duck, halibut, and of course a burger. The difference in presentation and execution, however, is significant. CCR also offers opportunities for splurging, among them caviar, a 30-day dry-aged rib eye, and tableside cocktail service. In short, there’s the requisite amount of variety in both dishes and pricing to satisfy the broad demands of a range of itinerant guests.

Unlike Remington’s, Cherry Circle Room has much to offer townies too: a majestic property, sure, but also a mostly well-executed menu. To start, a mineral-rich puck of coarsely chopped beef tartare alongside a drift of briny shaved Gouda forms the pedestal for a quail egg served upright in its shell, the top cut away for immediate dispensation once it hits the table. Slender lengths of tender grilled octopus entwine amid nutty romesco and piquant chorizo vinaigrette. Petite, sweet, clean-tasting rope-grown mussels bathe in red curry and lemongrass. A minimalist charcuterie board is laid with disks of fatback-jacketed venison paté and ribbons of concentrated duck breast prosciutto. You’ve likely encountered interpretations of these dishes numerous times if you’ve been in the habit of eating out in this decade, but they’re so nicely presented it’s difficult to be bored.

A deconstructed shrimp cocktail finds the sweet crustaceans splayed across a plate with celery leaf and a bright and acidic if oily cocktail sauce. A fresh Caesar salad substitutes deep-fried nuggets of smelt for both anchovies and croutons. Rare slices of aged duck are arranged upon a bed of wild rice and orzo and lacquered with a sumptuous roasted plum sauce. The Duroc pork chop arrives dissected as well, its slices situated amid farro, artichoke hearts, and a “clams casino sauce” that features whole bivalves.

Meanwhile the steak presentation rivals that of any of the nearby expense-account steak houses. The char on a 48-ounce tomahawk prime rib makes the steak look like it could cleave a skull in two, but its pink interior is lush, buttery, and rich.

The misses seem extra regrettable if only for the promise that they show. A terribly overcooked halibut fillet alongside a solid clump of squid ink pasta was paired with sweet peekytoe crab and the fish’s own poaching liquid—made in part with Paul McGee’s Bloody Mary mix. Desserts can be a disappointment too, particularly when familiar favorites are subjected to pointless deconstruction. There’s nothing satisfying about a few squares of dry carrot cake arranged around thick squiggles of cheesecake ganache—though the carrot-pineapple sorbet that accompanied the dish was interesting. Same goes for the intensely flavored miso-caramel ice cream that steals the show from an anarchic scattering of chocolate cremeux and pretzels.

A much more satisfying endgame would be one of McGee’s four boozy, lightly sweet cacao-and-vanilla ice cream drinks—each served in a minature milk bottle with a straw stuck in it—particularly the classic Pink Squirrel, nutty with Crème de Noyaux, and a subtly minty grasshopper.

For all the wonders of Cherry Circle Room, it does have one very serious shortcoming and a few structural flaws. While the bartenders are generally excellent, knowledgeable, and genial, table service is maddeningly negligent, with servers going AWOL for prolonged periods of time, extending meals far longer than they should be. The expansive leather booths are wonderful, but the puny two-tops pushed together for four guests are inadequate for any sort of comfortable gathering. Finally, a single handicap-accessible restroom located on the far end of the neighboring Game Room is frequently occupied, which forces most guests to descend the stairs into a dim, narrow corridor that recalls certain scenes in The Shining, then cross above the hotel’s mezzanine to access the men’s and women’s. It’s quite a long journey, so long that one evening a server told my tablemates he wouldn’t pour my water until I returned. He was afraid it would get too warm. I still didn’t see him again for a good long while.

But these are mostly surmountable problems. And once they’re surmounted, this old boys’ club is going to be an excellent retreat from the Michigan Avenue madness.  v