The 15 best wine bars in Chicago

The novella-length menu at this low-key Humboldt Park alcove contains loving and helpful descriptions of an impressive selection of wines. You can practically feel beverage director Jamie McLennan's passion oozing off the pages. The staff here is always happy to help point you in the right direction, 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.

Whether you're looking for a special bottle of wine to take to a dinner party or you're hankering for a loaded charcuterie board, this all-day cafe and bottle shop has you covered. The menu at All Together Now sources market-fresh produce from Midwestern farms and utilizes smoked and cured meats from Underground Meats in Madison, Wisconsin. Stop by throughout the day for hearty sandwiches and small plates, or plan a post-work outing for pillowy ricotta dumplings and ruby-red grilled hanger steak. Wines by the glass go for $12–$16, and a roster of local beers and coffees round out the menu.

If you're still trying to catch up on the natural wine trend, Webster's is a great place to start your boozy education. Founders Janan Asfour and Tom MacDonald source their bottles from small, family-owned producers, which means regulars are constantly treated to some fascinating pours. One of our favorite things about Webster's is that most varietals are offered by the glass, bottle and 2.5-ounce tasting, so you can easily build your own wine flight on the fly. It's easy to pace yourself with small plates like slow-braised pork belly, chicken croquettes and Spanish queso fundido.

This subterranean wine bar is all but hidden in a quiet pocket of 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 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).

An environmentally conscious wine shop, Red & White specializes in natural wines and hard-to-find and obscure booze in all forms. The storefront's wine bar unsurprisingly pours from the same vein, though guests can expect to find different bottles than what's available up front. The beautiful, modern space also serves a variety of small nibbles including kombu-cured fluke crudo, beet tartare and kuri squash ravioli.

From the folks who brought us beloved watering holes like Scofflaw, Slippery Slope and Heavy Feather comes this funky Logan Square wine bar pouring minimal-intervention wines by the glass and bottle. The 40-seat interior is outfitted in warm, intricate woodwork from Chicago design studio Threefold, and the sprawling warm-weather patio has room for 100. Outside Voices offers a tight menu of snacks and charcuterie, but critic-approved restaurants like Parson's Chicken & Fish and Giant are nearby if you're craving something heartier.

When your average wine night calls for a serious upgrade, grab a seat at Joe's Imports, a sleek and sexy wine bar situated in the heart of the West Loop. Before you start pondering the lengthy vino list, ask your server for an order of the fried parmesan puffs and the whipped ricotta. Once you've got some sustenance in front of you, peruse the drinkable options—which range from champagne and chenin blanc to brunello and syrah. Keep an eye out for the bar's namesake Joe Fiely (he's the operating partner and wine director for Francesca’s Restaurant Group), who hand-selected each bottle from his globetrotting travels.

Pulling its inspiration from cozy Italian wine bars, Figo offers almost 70 different kinds of vino in a rustic-modern space that's anchored by a long, tile-lined bar. Go early in the evening to watch the sun go down through the sprawling front windows, or roll up at the end of the night for an order of tiramisu and a glass of prosecco. The dinner menu is killer, too, with highlights like the crispy arancini, truffle-scented gnocchi and chimichurri-smothered hanger steak.

The Spanish word "penumbra" translates to "partial darkness," which is a fitting name for this dimly lit Logan Square wine bar that locals flock to. The menu is approachable, with a curated selection of pours available by the glass as well as a laundry list of bottles to choose from. The dinner menu offers more than small snackables, with a lineup of steaks, seafood, hearty vegetarian dishes and a handful of desserts.

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.

This sunny Andersonville bakery transforms into a refined wine bar by night. Lattes are replaced with natural wines, and savory small bites sub in for breakfast pastries. Choose from a one-page lineup of by-the-glass pours and bottles before ordering a smorgasbord of bites for the table (Swedish meatballs and chicken live mousse are musts). No trip to Lost Larson is complete without a slice of Princess Cake, and lucky for us, it's available on the VinBar menu, too.

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 and extra-large patatas bravas fries. 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.

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.

This combination wine shop and bar has a few outposts scattered throughout Chicago, but we most enjoy hanging out at the West Town location, where you'll find a sizable glass list and an abundance of drinking snacks to pad your belly with. And since you're already here, you should take home a bottle or two of wine. For convenience sake, of course.