The 8 Best Wine Bars in Chicago

If you’re serious about your wine, award-winning Webster’s Wine Bar is the spot to know. Allow the knowledgeable sommeliers – who have learned first-hand from winemakers all over the globe – to help you navigate the extensive menu. The wines (around 20 different types available by the glass, and over 500 bottles in the cellar) are intended to represent the region they’re from, and the selection includes organic and biodynamic varieties. Look out for specials at the start of the week, including food and drink deals and discounted unusual bottles from the depths of the cellar.

DiSotto Enoteca means “underground wine bar” in Italian, and true to its name this spot has a decidedly cave-like feel with a curved red brick ceiling and walls lined with wine bottles. The bar’s well-edited selection of wines features over 100 European and American varieties, and the menu of light bites skews Mediterranean. When you’re ready for a nibble, opt for the truffled-egg toast with shaved asparagus and fontina cheese – a DiSotto Enoteca classic.

Enolo takes the brainpower out of deciphering wine varieties, with a compact and curated menu of delicious options. If you still can’t make up your mind, try a three-glass flight: either crisp and vibrant, floral and fruity, or textured and complex. All wines are picked to complement the Italian-influenced food menu. Order the burrata to start, which is served with cherry tomatoes, artichokes, olives, prosciutto and pine nuts. Then double down on the cheese theme with a bruschetta topped with creamy brie, sour granny smith apples, gooey fig jam, and a drizzle of wildflower honey.

Gather is the first restaurant to open under the Community Food + Wine group – a collective that aims to open neighborhood dining destinations with a welcoming vibe, locally grown food and approachable wine list. Patrons are encouraged to sit at the kitchen counter, where they can watch the chefs prepare dishes like steamed Parisian gnocchi, steak tartare, crispy cauliflower with mango salsa and pork belly spaghetti – all while sipping a glass of icy sauvignon blanc. Gather your nearest and dearest for the restaurant’s Sunday Dinners, a family-style feast with wine pairings to see out the week.

Rootstock Wine & Beer Bar was founded by former employees of Webster’s who know their Old World grapes from their New World ones. This homey local spot in Humboldt Park finds its niche in small-batch wines from unusual places with an emphasis on organic, local, and biodynamic varieties. Try a glass of brut rosé from Austria, a vin des letinon from Greece or a riesling from Germany. Rootstock serves dinner until 1am, making it a great late-night spot to graze on charcuterie and cheese boards, or – if you’re after something more substantial – dry aged burgers and spring risotto with smoked mushroom, English peas, egg yolk, and parmigiano reggiano.

Sister restaurant of acclaimed Zia Trattoria in Edison Park, Lago Vista shares the same acclaimed Italian dishes, while emphasizing an appreciation for wine. Zia’s wine selection, which focuses primarily on American and Italian-produced bottles, is curated to complement the food menu: a mouthwatering carb-heavy spread including elaborate pizzas, hearty pastas and classic seafood dishes. The space is designed to feel like an Italian wine bar, with high ceilings, arched windows and a central horseshoe-shaped bar you’ll want to perch at for a leisurely evening of wine tasting.

Known as the ultimate venue for Chicago celebrations, Pops for Champagne has the largest selection of bubbly in the city: 150 types to be exact. Every surface in the bar is shiny and metallic, which feels right for a venue that specializes in sparkling wines and effervescent cocktails. Grab a stool at the bar and sip your Champagne of choice while one of the city’s best jazz bands plays live. And if you get peckish, there’s also a seasonal menu of share plates designed to complete your Champagne-fueled evening.

The owner of Penumbra hails from Ecuador, so expect Latin American wines and food at this intimate bar. The back dining room is decorated in warm tones, draped fabrics and candlelight – a cozy atmosphere for long dinners with good friends. Dishes at Penumbra are predominantly meat and seafood-based, with rubs, marinades and reductions that add Latin flair. Penumbra’s wine menu boasts bottles from some of the best vineyards spanning Chile, Argentina and beyond.