Avec | West Loop | $$$
At first, sitting on a bench between strangers in this cedar-lined, saunalike room makes me feel a little apprehensive, like I'm wrapped in naught but a sweaty towel. But as the wine flows and the evening grows long, everyone's gabbing like pals, offering around bits of robust cheese or chorizo-stuffed dates and dredging juices off empty plates with warm rustic bread. Chef Koren Grieveson's Mediterranean "peasant" food is paired with an ever intriguing and ever changing selection of uncommon wines and cheeses, many of which are as unforgettable as the Spanish sheep's-milk torta del casar, a powerful molten gob of delicious funk that may forever remain my benchmark for strong queso (if only because I couldn't seem to wash the smell from my fingers). The chefs make excellent and varied use of the wood-burning oven, firing up everything from focaccia to roast chicken, hanger steak, and skate wing. And it never ceases to amaze me how combining just two or three seasonal ingredients—say, springtime's baby asparagus, smoked mozzarella, and Meyer lemon vinaigrette—can be, in the right hands, a kind of alchemy. —Mike Sula 615 W. Randolph, 312-377-2002, avecrestaurant.com. Dinner: daily. Open late: Fri & Sat till 1, Sun-Thu till midnight.
Bin 36 | River North | $$$
A unique hybrid of retail wine store, casual bar, and formal dining room from restaurateurs Dan Sachs and Joanne Chessie, executive chef John Caputo, and wine director Brian Duncan, who aim to demystify the process of matching wine with food. Curved racks of wine divide the retail corner from the bar, which serves tasting portions of light, eclectic fare ranging from seafood sliders and charcuterie to burgers. The vast selection of wines is organized into "bins" of four or five related wines with associated bin numbers, several of which appear on the menu next to each dish. The restaurant also offers flights of two-and-a-half-ounce tasting portions. The cheese selection is first-class—now more than ever. Servers are, of course, wine savvy. —Laura Levy Shatkin 339 N. Dearborn, 312-755-9463, bin36.com. Breakfast, lunch, dinner: daily. Open late: Fri & Sat till 1, Thu till midnight, Mon-Wed till 11.
DiSotto Enoteca | Gold Coast/Mag Mile/Streeterville | $$
Scott Harris's quest for world domination proceeds apace with this snug wine bar in the basement below Francesca's on Clark. The menu of small bites, bruschetta, cheese, and charcuterie owes a great deal to Harris's Taylor Street hit Davanti Enoteca—so much so that one wonders if he's deliberately trying to dilute their mutual brands. He's certainly not trying to reinvent the wheel with the minimally prepared plates, winningly with truffle egg toast—essentially Toad in Hole with very slight truffle accent, and a supercreamy jar of ricotta you're meant to mix with a dollop of honeycomb. The charcuterie—at least the soppressata—is nothing special, but gets the job done. In any case it's not a bad little spot—dark with a vaulted brick ceilings—to work your way down the extensive wine list, with a few perfectly acceptable little bites. —Mike Sula 200 E. Chestnut, 312-482-8727. Dinner: daily. Open late: Sat till 3, Fri till 2, other nights till 1.
Fork | lincoln square | $$$
It's hard to imagine a cozier place than Lincoln Square's Fork (formerly Fiddlehead Cafe), with its warm tones, exposed-brick walls, and soft lighting. Its most notable feature is the extensive beer and wine list; both menus are arranged into flights, with small pours (as well as full-size ones) of several dozen beverages available. You can pick a suggested grouping like "interesting whites" or mix and match, and there are a bunch more options by the bottle. And while the food menu is less encyclopedic—several selections each for snacks, soups and salads, sandwiches and burgers, and small-to-large plates, plus charcuterie and cheese—the execution is solid. Fried onion strings with house-made ketchup were crispy and subtlely oniony, candied bacon wasn't overly sweet, and the grilled hanger steak had a nice crust. Portions are relatively small, so this place may be better for a beer and a snack than a full meal; gnocchi with "foraged mushrooms," while light and fluffy, also worked out to more than a dollar per largeish nubbin. Still, the staff was unfailingly friendly, and when we lingered after paying the bill, our server, rather than giving us the evil eye, brought us complimentary half glasses of sparkling wine. —Julia Thiel 4600 N. Lincoln, 773-751-1500, forkchicago.net. Dinner: Sun, Tue-Sat. Sat & Sun brunch. Open Late: Fri & Sat till midnight, Thu till 11.
In Fine Spirits | Andersonville | $$
This sleek but cozy wine bar, from the owners of the adjacent In Fine Spirits retail store, is a hot spot on an Andersonville strip known for its lambics and glogg. The ample menu of accessibly priced glasses and flights is dominated by New World wines and augmented with classic cocktails and a choice selection of craft beer. There's an abbreviated rotating menu of cheese, charcuterie, and a bunch of plates for nibbling and noshing. And, of course, should you fall for a particular juice, you can always come back when the store's open and make it your own. —Martha Bayne 5420 N. Clark, 773-334-9463, infinespirits.com. Dinner: daily. Open late: Fri & Sat till 2, Mon-Thu till midnight, Sun till 11.
Marion Street Cheese Market Cafe | oak park/river forest | $$
Marion Street Cheese Market Cafe lays out exquisite cheeses, meats, and local produce, done up as small plates and entrees—but not too done up. The cafe specializes in noninterventionist cuisine, manipulating its plates minimally and setting them forth in ways that foreground the undiluted goodness of artisanal chow. Wine and beer flights are well paired with cheese and charcuterie, affording tiny tastes of many good things, which is what this cafe is all about. Don't come here expecting a bellyful; instead, seek to sample simple dishes like smoked pork with sweet potato hash or prosciutto with mango, sip a tasty beverage or two, and leave feeling very satisfied but not stuffed. —David Hammond 100 S. Marion, 708-725-7200, marionstreetcheesemarket.com. Breakfast, lunch, dinner: seven days. Open late: Friday & Saturday till 11.
The Purple Pig | river north | $$ Snout-to-tail cooking is the name of the game at the Purple Pig, a convivial take on an Italian enoteca from Scott Harris (Mia Francesca), Jimmy Bannos Sr. (Heaven on Seven), and chef Jimmy Bannos Jr., who honed his skills at Mario Batali's New York restaurants. While there was no actual snout, sow's ear became the proverbial silk purse in crunchy-chewy fried strips with crispy kale, marinated cherry peppers, and a fried egg to mix in, all served in a cute wine-colored pig bowl. Sections of tender pig's tail braised and glazed in tart balsamic were draped with a little egg salad, making me wonder if Bannos was riffing on bacon and eggs. But not all the pleasures are porcine at this noisy spot. Of our four cold antipasti, expertly seasoned giant Greek lima beans paired with olive-oil-poached tuna was the favorite, followed by brown-butter-caramelized butternut squash with pumpkin seeds and ricotta salata. Brussels sprouts shaved to a fine slaw were so cheesy with Pecorino Foglie di Noce and Parmigiano Reggiano they seemed geared toward people who don't like brussels sprouts. Hot and cold complemented each other in crisply fried sardines over a refreshing salad of shaved fennel in a lemon vinaigrette laced with capers, pine nuts, and currants. Pomegranate seeds beautifully set off a glossy golden quail on a puddle of salsify puree ringed by a drizzle of pomegranate syrup. The highlight of our trio of cheeses was Podda, a nutty Sardinian cheese made from a blend of sheep's and cow's milk. The all-European wine list has scores of bottles for $40 or less, and quite a few are also available by the glass or quartino. Reservations aren't accepted. —Anne Spiselman 500 N. Michigan, 312-464-1744, thepurplepigchicago.com. Lunch, dinner: daily. Open late: Fri & Sat till 1, other nights till midnight.