The best wine bars in Chicago

The novella-length menu at this low-key alcove contains loving and helpful descriptions of an impressive selection of wines and beers. And thanks to the array of small plates served until 1am, this is the kind of warm, simple neighborhood place you’ll never want—or need—to leave.

Webster’s Wine Bar relocated from Lincoln Park to Logan Square (where it took over sister spot the Telegraph), but little has changed. It's still a solid place to sample an array of wines, since tasting pours are about $4.50–$7, and the knowledgeable staff and engaging menu descriptions will direct you to the right wine. The cheeses and charcuterie plates are just what you need to soak it all up.

This subterranean wine bar is all but hidden on a quiet corner in the West Loop. But once you step inside, you'll get the sense that it's every nearby residents' favorite secret. Situated below upstairs bed-and-breakfast Publishing House, the Press Room offers a robust selection of special wines by the glass and bottle. Sip picks from Chile, Spain, Argentina, Israel, Washington and beyond. Pours are best paired with La Grande Board, an assortment of charcuterie and cheese, or the salty boquerones (Spanish anchovies, cultured butter and radish on grilled sourdough).

Generally speaking, income tax isn’t something we’re thrilled about. Income Tax, a wine bar in Edgewater, on the other hand, is a place you should get excited about. The neighborhood spot offers a knockout selection of inspired bites, but the big decisions are reserved for the exhaustive wine and spirits menu. If you're looking for wines by the glass, there's a concise list of options—from prosecco and rosé to cabernet Franc and syrah.

Pintxos and porrons are highlights of Lettuce Entertain You's first-ever wine bar. The sultry River North hideout offers a curated menu of approachable pours from small, sought-after producers alongside a lineup of small plates like pan con tomate, blistered shishito peppers, spicy clam ceviche and potato croquetas. Kick things up a notch by ordering a porron (a glass wine pitcher that's used to pour wine into your mouth) of Txakoli for the table to share.

The restaurant attached to Lakeview's Pastoral is a dim, cozy spot for drinking an interesting selection of wines by the glass, along with the food you want while sipping wines—cheese plates, charcuterie and pâté. Half glasses of wine are just $5–$8, so you can sample a variety. If you like what you taste, well, Pastoral's shop is just next door.

You enter through an unmarked alleyway, glowing strings of lights leading you to a cobblestone courtyard and ornate parlor that resembles a Parisian hideaway. You forget where you are. You order glasses of champagne you’ve never heard of, you gently unhinge oysters from their shells, and when dessert comes, your selection is plucked from a fanciful cart, replete with bite-size marshmallows. Heaven? Who needs it when there’s RM?

An approachable wine bar, Enolo offers an edited list, knowledgeable and enthusiastic servers and wine flights so you can try a trio of different pours. The food menu is just as friendly, with familiar small bites, salads, panini and a few entrees. We're particularly fond of the bruschettas—especially the artichoke with Parmesan and shallot and the French brie with apples, fig jam and wildflower honey.

This sleek, shiny bar in Tree Studios boasts—as the name suggests—the city’s best selection of bubbles. Most of it doesn’t come cheap (it never does), but you’re not just paying for the booze—you’re paying for some of the most educated bartenders in town. Take advantage of their knowledge and ask lots of questions. And when you’ve had enough education (and wine), head downstairs to Pops’ cocktail bar, WaterShed.

Old World wine list and Mediterranean small plates: Scott Harris has nailed the formula at Purple Pig and Davanti Enoteca, so why mess with a good thing? Admittedly, the scales at DiSotto (in the cellar-like basement of Francesca’s on Chestnut) tip toward drinking—the food is limited to antipasti, bruschetta, cheeses, salumi and a small selection of pasta. But when you’re spreading thick ricotta and fragments of honeycomb on toasted bread or sampling warm, marinated olives or indulging in the toast with a truffled egg yolk at its center, the appeal of this wine bar can’t help but feel unending.