Best Wine Bars in Chicago


Chicago is well-known for its world-class shopping, Chicago Cubs baseball, and Chicago-style pizza. But did you know they’re also a hotspot for high-end wine bars?

From the warm, lounge-like settings to the perfectly made cocktails and educated wine waiters that frequent such establishments, a good wine bar always feels like home. It’s also a great time to catch up with friends and family and have some quality chat. The greatest bars in Chicago provide outstanding service, quality beverages, and tasty food, regardless of your level of wine experience or whether you like wine or not.

An excellent wine bar does not require you to be a level 10 master sommelier. There will be no blind taste tests or questions concerning Bordeaux weather patterns during Baron Haussmann’s reign. So, whether you’re a working-class wine enthusiast or just dabbling in whites and reds, these Chicago wine bars will provide the ideal setting. Let’s get to the good stuff!

Rootstock Wine & Beer Bar

954 N California Ave, Chicago, IL 60622
Phone: 773-292-1616

On the corner of N. W. California Avenue and California Ave. Rootstock Wine & Beer Bar, located on August Blvd, is a fashionable wine bar with a relaxing, lounge-like environment.

Their emphasis is on serving small-production wine and beer, and they provide a wide range of beverages by glass or bottle. This quaint but often-overlooked tiny restaurant created by three former Webster’s Wine Bar employees focuses on small-batch wines and brews with an emphasis on organic farming. They are pouring palate-pleasing varietals from South Africa to Slovenia, as well as an unusually big Greek and German contingent, in addition to the normal French and Italian wines.

They also have a Moody Tongue Caramelized Chocolate Churro Baltic Porter, a beautifully under-the-radar dry-aged Slagel Family Farm burger, and a Sunday brunch where you can order bratwurst. So, what exactly are you waiting for?

All Together Now

2119 W Chicago Ave, Chicago, IL 60622
Phone: 773-661-1599

This all-day cafe and bottle shop has you covered whether you’re searching for a unique bottle of wine to go to a dinner party or a loaded charcuterie board. All Together Now’s menu features market-fresh food from Midwestern farmers, as well as smoked and cured meats from Underground Meats in Madison, Wisconsin. Stop by for hearty sandwiches and small dishes throughout the day, or plan a post-workout outing for pillowy ricotta dumplings and ruby-red grilled hanger steak. Wines by the glass range from $12 to $16, and the menu also includes a selection of local beers and coffees.

All Together Now is a beautiful restaurant and wine shop that caters to social groups. The business, which is located in Chicago’s Ukrainian Village, is a pleasant, well-lit room ideal for wine and cheese tastings, lessons, or eating a delicious lunch. In addition to a large assortment of cheese, All Together Now offers handcrafted bagels, fruit preserves, and crackers.

Webster’s Wine Bar Chicago

2601 N Milwaukee Ave, Chicago, IL 60647
Phone: 773-292-9463

Webster’s is a wonderful place to start if you’re still attempting to catch up on the natural wine trend. Janan Asfour and Tom MacDonald, the company’s founders, obtain their bottles from tiny, family-owned manufacturers. Ensuring that regulars are always treated to some intriguing pours. One of the favorite aspects of Webster’s is that most varietals are available by the glass, bottle, and 2.5-ounce taste. Allowing you to quickly create your own wine flight. Small meals like slow-braised pork belly, chicken croquettes, and Spanish queso fundido make it easy to pace yourself.

They think that serving wines without additions or chemicals allows the true flavor of the wine to show. In addition to a wide selection of high-quality wines, they also provide specialty cocktails and spirits.

The Press Room

1134 W Washington Blvd, Chicago, IL 60607
Phone: 331-240-1914

This subterranean wine bar is nearly concealed in a quiet West Loop neighborhood. However, once inside, you’ll get the impression that it’s every surrounding resident’s best-kept secret. The Press Room, located below the upper bed-and-breakfast Publishing House, provides a diverse selection of wines by the glass and bottle. Sip selections from Chile, Spain, Argentina, Israel, Washington, and other countries. Pours go well with the La Grande Board, a selection of charcuterie and cheese, or the salty boquerones (Spanish anchovies, cultured butter, and radish on grilled sourdough).

They include private dining choices for special occasions, a wine club, and a happy hour every Tuesday and Wednesday from 4-6 pm with $7 cocktails and $1 raw oysters.

Red & White Wines

1861 N Milwaukee Ave, Chicago, IL 60647
Phone: 773-486-4769

Red & White, an environmentally concerned wine boutique. Specialized in natural wines as well as hard-to-find and esoteric liquor of all kinds. The wine bar in the storefront, predictably, serves from the same vein. Though guests should expect to find different bottles than what’s available out front. In addition to kombu-cured fluke Crudo, beet tartare, and Kuri squash ravioli, the gorgeous, modern setting serves a range of small bites.

Red & White Wines has been delivering artisanal wines to their guests in the Bucktown neighborhood since 2008.

The wine bar is a fun place to go on a date or with the company, and they also have wine tastings on Saturday afternoons. They sell wines from all around the world at a variety of rates.


3309 W Fullerton Ave, Chicago, IL 60647
Phone: 773-772-2343

The Spanish word “penumbra” translates to “half darkness,” which is an apt name for this darkly lit Logan Square wine bar frequented by locals. The menu is simple, with a selected selection of pours by the glass and a long list of bottles to pick from. The evening menu is more than just little snacks, featuring steaks, seafood, hefty vegetarian entrees, and a few desserts.

Penumbra, a wine bar in Chicago’s Logan Square, is located there. Latin-inspired American cuisine is served in a warm. A softly lighted setting is ideal for a romantic evening or a special occasion with friends and family.

Joe’s Imports

813 W Fulton Market, Chicago, IL 60607
Phone: 312-736-1750

Take a seat at Joe’s Imports, a sleek and sensual wine bar located in the center of the West Loop. When your regular wine night needs a serious update. Before you start thinking about the extensive wine selection, have your server bring you some fried parmesan puffs and whipped ricotta. After you’ve finished your meal, examine the drinkable alternatives, which include champagne and Chenin blanc, as well as Brunello and syrah. Keep an eye out for the bar’s namesake, Joe Fiely (the operating partner and wine director for Francesca’s Restaurant Group), who hand-selected each bottle from his world travels.

They provide excellent Mediterranean cuisine alongside a large range of world-class wines in an elegant and pleasant setting.

Summer Thatcher
Summer Thatcher
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