Keeping It Classic
Atwood Cafe: Derek Simcik will dish up a three-course, Roaring '20s-inspired feast at this hotel-centered, central Loop American on February 14. Expect Caesar salad, oysters Rockefeller and tarragon-scented lobster Thermidor ($48 per person, plus $30 for wine pairings; 312-368-1900).
Harry Caray’s: Keeping it tried-and-true, this sports-minded River North steakhouse will serve a candlelit surf 'n' turf menu on February 11, 12 and 14, with an add-on option of oysters with Pinot Noir mignonette ($110 per couple, plus $11.95 for oysters; 312-828-0966).
Lawry’s the Prime Rib: If it isn’t broke, don’t fix it is the mantra at this venerable River North steakhouse, which will serve a prime rib dinner for two February 10-14. The three-course meal kicks of with its signature spinning salad bowl, followed by tableside-carved beef or oven-roasted salmon with braised cabbage and cannellini bean ragout. For dessert? Chocolate-raspberry linzertorte to share, plus hot fudge sauce to go - wink, wink ($99; 312-787-5000).
Beyond Meat and Potatoes
Carnivale: Score a table at this kaleidoscopic Latino perched on the outskirts of the Loop. Then, choose from à la carte specials like spicy shrimp soup ($9), oyster shooters ($5) and a tomahawk rib-eye ($48), which are available February 10-14 (312-850-5005).
Cocoro: Canoodle over shabu-shabu or sukiyaki at this Japanese in the North Center neighborhood, and receive a complimentary appetizer and $15 gift certificate to use down the road ($56 for two; 312-943-2220).
Frontier: Set aside preconceived notions for the meat-laden, four-course menu offered February 11-14 at this lodgelike Noble Square gastropub. But come with a stomach of steel, since beef heart tartare and sugar cane-skewered lamb heart are part of the equation ($30 per person or $50 per couple; 773-772-4322).
Money’s No Object
Sixteen: An extravagant, five- or eight-course menu awaits at this panoramic hotel dining room in River North, though it’s important to note no other menus are available on February 11 and 14 (5:30 PM-9:30 PM; $165 or $235 with wine pairings per person for five courses, $335 per person for eight courses, including wine pairings; 312-588-8030).
Familiar, but Tweaked
Custom House Tavern: If preordained eats aren’t your thing, head to this New American in Printer’s Row, where a choose-your-own, four-course feast is available. Like broccoli-cheese soup? It’s complemented with grilled pimento cheese and pickled broccoli. Crave the other white meat? Go for the grilled pork loin chop, plated with roasted celery root and purée, spiced peanuts and apple cider, from February 11-14 ($55 per person, plus $40 for wine pairings; 312-523-0200).
The Florentine: Cozy up to seasonal Italian eats in the Loop, February 11-14, when à la carte faves like bucatini carbonara ($14 for a half-order or $26 for a full) will be served alongside aphrodisiac-esque specials, such as chilled Kumamoto oysters on the half shell with cucumber mignonette ($16) and tagliatelle with Parmesan and Perigord black truffles ($50; 312-660-8866).
Shaw’s Crab House: Don’t be a crab, but eat lots of it during a grand crab buffet on February 11 and 14 at this Schaumburg seafooder, where king, Dungeness and snow will fuel temptation. Crab cakes, lobster tails, sushi and fried shrimp are part of the spread too. Chocolate-covered strawberries at meal’s end? Yes, indeed (5:30 PM-9 PM; $56 per person; 847-517-2722).