West Town Tavern
West Town Tavern's got a delectable menu and a subtly romantic vibe to match. This year's Valentine's Fourplay Dinner for Two gives diners several options for starters, entrées, and a shared dessert platter, plus a parting gift--two house-made truffles to go...so the sweetness continues. Monday, February 14, $48 per person.
1329 West Chicago Avenue; 312-666-6175.
Chef Guy Meikle celebrates Valentine's Day all weekend with a $65 prix-fixe menu. We don't want to spoil everything, but there are buttermilk fried oysters involved, okay? Nana's also rolling out special cocktails, and one is included in your meal. We'd pick the Dotted with Hearts, a mix of Rum, jasmine green tea, coconut water, pinaeapple, and citrus. Thanks Cupid. February 11-14.
3267 South Halsted Street; 312-929-2486.
Down in the Loop, romance is brewin'. Chef Derek Simcik has invented a 3-course Shareables menu for two. Look for perfect mood food like brie and foie torchon, and oysters, of course. February 11-14, $45 per person or $65 with wine pairings.
1 West Washington Street; 312-368-1900.
South Water Kitchen
South Water Kitchen gets playful this year with its Perfect Pairs menu. Enjoy like a kid, but dine like a grown-up on "peas and carrots" (a sugar snap pea salad with carrot ginger vinaigrette), and other fun menu twists. February 11-14, $40 per person or $60 with wine pairings.
225 North Wabash Avenue; 312-236-9300.
Let's not neglect the third wheels in our lives this Valentine's Day. Sable will let your tagalong eat for half-price this V-Day weekend. Valid only for parties of three, you, your date, and your...extra can enjoy butter poached lobster and one of Sable's mind-blowing original cocktails. Cozy. February 11-14.
505 North State Street; 312-755-9704.
Are you ready for this? Valentine's Day is the one night a year that Lula Cafe takes reservations. For $70, enjoy a one-night-only, 7-course tasting menu. We can't pick a favorite, but the risotto with duck prosciutto is looking really promising. February 14.
2537 North Kedzie Boulevard; 773-489-9554.
Kith & Kin
If you want to share the love this Valentine's Day, head to Kith & Kin. On February 13, you'll find a couples menu complete with wine pairings, featuring five of the most decadent and inspired courses we've ever seen. We're talking chocolate cake with violet gel and earl grey crème cheese. Now that's love. $250 per couple, gratuity included.
1119 West Webster Avenue; 773-472-7070.