Michigan Avenue is Chicago’s most gilded boulevard, but it’s never been dining heaven. Sure, there’s Spiaggia at the top of the Mag Mile, the Purple Pig north of the river, and the Gage and Acanto giving it their all across from Millennium Park. But otherwise the strip is full of interchangeable fare, served up at Bandera, Howells & Hood, Sweetwater Tavern & Grille, and such benign big-chain feedbags as the Cheesecake Factory. A prohibition on valet parking doesn’t exactly encourage adventurous restaurateurs. Basically, all a Michigan Avenue restaurant needs to do is sate the undiscriminating bellies of shoppers and looky-loos with familiar food and drinks and it’ll do fine.

So 4 Star Restaurant Group (Dunlays, Frasca, Smoke Daddy) shocked no one when it opened Remington’s, a 250-seat grill facing Millennium Park, in May. What is surprising is that the menu of straight-down-the-middle American food (steaks, salads, soups, and sandwiches) comes from Todd Stein, a creative chef best known for his world-beating pastas at Cibo Matto, the Florentine, and Piccolo Sogno Due. This is like hiring Matisse to paint your bathroom.

Remington’s is 4 Star’s most ambitious project to date, and it’s sharp-looking, if entirely forgettable. The deep space, divided by a wine-bottle wall, abounds in smooth wood paneling and secluded black leather booths. Massive flat-screen TVs dominate the slick bar area up front, but so do enormous windows with tantalizing views of the park. Aesthetically speaking, it’s a wash.

The food fares similarly. You’ve got predictable starters at pumped-up prices, such as a bright and chunky guacamole for $10, three deviled eggs stuffed with lobster for $12, and a spinach-artichoke dip for $12 that tastes as if it came straight from Houlihan’s up the street. Crisp toast topped with lime-tinged crab, sliced red peppers, and avocado purée makes a good enough impression. And the weird but ingenious salad of blanched Brussels sprouts with dried blueberries, bacon-flavored almonds, and shredded Manchego effortlessly balances unlikely flavors.

The Remington, an 18-ounce bone-in strip steak, glistens with juice, glorious char lines, and a brazen layer of fat melting into prime dry-aged beef. Among the menu’s “American classics,” the only other dish that reaches such heights is a terrifically flaky branzino (because nothing says American classic like Mediterranean sea bass) in a little brook of lemon-butter sauce with a gently sautéed tomato and firm Broccolini stems.

Low-key servers strike just the right chord: pleasant, prompt, and playful. At times, they push the pace a tad too much, but they also push the rich and top-notch Key lime pie. With a perfect buttery graham cracker crust and punchy lime, it hasn’t been whisked into soupy oblivion like so many Key lime pretenders.

Remington’s doesn’t break any new ground, nor does it intend to. The built-in crowds, from smoochy date-nighters to sunburned park-hoppers, never stop coming. While the kitchen shows hints that it could be more than a bland bourgeois diversion that serves fall-off-the-bone barbecue ribs or French dip sandwiches, the real question is why 4 Star bothered to enlist a chef as skilled as Todd Stein only to churn out barbecue ribs and French dip sandwiches.

“Turn right at the bocce court,” I’m told when I ask for directions to the bathroom at Cherry Circle Room. A block south of Remington’s, the four-month-old spot from Land and Sea Dept. (Longman & Eagle, Parson’s Chicken & Fish) must have the most diverse and discombobulating surroundings of any restaurant in town.

From the street-level foyer with a Byzantine tile floor, a curved marble staircase leads up to the former Chicago Athletic Association (circa 1893), now the lobby of the clubby Chicago Athletic Association Hotel. Through a doorway is the Game Room, a cavernous wonderland full of rowdy guys with retro cocktails woo-hooing over shuffleboard, foosball, pool, and, yes, bocce (all free).

Keep going. In a far corner, marked by a white neon insignia that looks like it could be for some kind of sub-Freemason hideout, you will find the entrance of the restored Cherry Circle Room. By this point, anything short of a trapeze show in a penguin sanctuary would be a letdown. But the restaurant is like the hidden library of your eccentric but wealthy uncle—here a bust of Abraham Lincoln, there a deep-sea diver’s helmet. The swank environs radiate a glow from cherrywood shelves and dimly lit golden orbs.

Only some of the eclectic comfort-food offerings by Peter Coenen (Boka, Gage) exude the same quirky confidence. The best example was a creative play on risotto made with farro, fava beans, and spring peas and served in a sea urchin shell that looks like a hula skirt. I wanted every dish to be so gloriously unhinged. Some come close, such as the raw bar’s silky tuna crudo with Kalamata olive chimichurri, which gets a promising crunch from tiny chicharrón, and the tender grilled Spanish octopus with Marcona almond romesco, pineapple, and chorizo vinaigrette.

But too many of Cherry Circle Room’s dishes get undone by carelessness in the back and front of the house. Loved the Eastern flavors of the steamed bouchot mussels in lobster broth with coconut and red curry; shuddered at the number of mussels that would not open. Shook my fist at the deep reservoir of roasted plum sauce that gunked up otherwise lovely medallions of glazed duck with confit leg and a mix of orzo and wild rice. And just felt sad for the 12-ounce double-cut Châteaubriand, which a nervous young staffer mangled tableside with a knife shakier than Boris Yeltsin at last call. By the time the poor guy finished, the beef was cold and destroyed, as were the three giant onion rings orbiting it.

Drinks, whether conceived by cocktail superstar Paul McGee or re-created from Jacques Straub’s century-old recipes, hit their marks. My waitress described the Byrrh cocktail—an appealing mix of the obscure French apéritif, rye whiskey, and sweet vermouth—as “a Manhattan in reverse.” (My joke that I would be hung-over yesterday did not land.) And Kristine Antonian’s ambitious desserts include an impressive deconstructed carrot cake lounging on a curved wood plank with pineapple-carrot sorbet, cheesecake ganache, sesame seeds, and pineapple. Unnecessary? Sure, but it looks and tastes like an outtake from Chris Nugent’s singular Goosefoot.

All told, dining at Cherry Circle Room is a peculiar experience that never quite coalesces. Still despite its shortcomings, there’s an odd charm to the place. But if, on your way to the washroom, you get clocked in the head with a bocce ball hurled by a daiquiri-hoisting bro, all bets are off.