Wine afficionados appreciate our fair city for one reason: wine bars in Chicago never disappoint. From themed décor to classic ambience, from historic architecture to sleek, modern design, these vino hot spots will satisfy your inner connoisseur. With most restrictions lifted, the social scene is vibrant again! It’s the perfect time to uncork, relax, and enjoy your favorite sip.
7 Hand-picked Wine Bars in Chicago
Webster’s Wine Bar – 2601 N Milwaukee Ave
Logan Square is home to many wine bars, but Webster’s is one of the only bars around focusing on natural, organic, and “minimal intervention” wines. With over 400 different selections to choose from, Webster’s also serves small plates and appetizers you can enjoy outdoors or in their unique “library lounge”. They’re open Tuesday through Sunday; glasses average around $12.
Frasca Pizzeria + Wine Bar – 3358 N Paulina
Frasca has a slightly smaller selection of wine, most of which comes from Italy and California to provide the perfect complements to their delicious, homemade Italian food. Frasca prides itself on being both party friendly and family focused; it’s a wonderful gathering place for almost any occasion. Located in Roscoe Village and open daily, expect to pay around $62 per bottle. You can also stop by for happy hour every weekday from 4pm until 6pm.
J9 Wine Bar – 1961 N Halsted
There’s something for everyone at J9 Wine Bar. Wine offerings are available at all price points—ranging from retail bottles (all under $29) to special reserves (as high as $440 per bottle). J9 also serves charcuterie boards and custom-made “wine chips” designed to pair with specific types of wine. This hip neighborhood fixture began as a meeting place for friends to catch up with one another. As a result, the same atmosphere still pervades. Located in Lincoln Park, they’re open every day and have plenty of outdoor seating.
Printer’s Row Wine Shop – 719 S Dearborn
You can’t discuss wine bars in Chicago without mentioning the historic Printer’s Row Wine Shop in the South Loop. This hip, rustic bar is open every day and includes a retail shop with wine service (available Thursday through Saturday). Enjoy some small plates and snacks at the bar, or outside on the patio. At an average of $15 per glass, an evening spent indulging with friends at Printer’s Row won’t break the bank, and the wide selection means you won’t ever run out of new things to try.
Penumbra Restaurant & Wine Bar – 3309 W Fullerton
Atmosphere reigns at Penumbra Restaurant & Wine bar. Dimly lit and inviting, this is just the place to meet new people, gather with old friends, or just enjoy some fine ambience on your own. Boasting an impressive and delectable Latin-inspired menu featuring lots of proteins, there are also plenty of vegetarian options. Penumbra is open Wednesday through Sunday, with a half-off happy hour (glasses of wine only) offered every Wednesday from 5pm until 6:30pm. They also host free wine tastings from time to time, so keep an eye out for their next event.
Scofflaw – 3201 W Armitage
This trendy, causal destination is perfect when you want a good glass of wine, but the rest of your group wants cocktails. Scofflaw is cocktail focused, but their handpicked wine selection—available by the bottle or by the glass—is the perfect solution. The dinner menu includes plenty of gluten-free options for those with allergies, as well as some excellent vegetarian dishes. Enjoy food and drinks indoors or on the patio every day, from 5pm until midnight. Or, if you’re in the area, try out their weekend brunches, available every Saturday and Sunday.
Rootstock Bar – 954 N California Ave
If your ideal outing includes a fine array of small plates and fancy cheeses to accompany your favorite bottle, look no further than Rootstock Bar in Humboldt Park. Modest and warm décor complement Rootstock’s unique focus on organic, biodynamic farming practices, just like their cheese boards complement their wine. The dishes they serve are ultra-fresh, using locally sourced produce. Bottles average around $45 and outdoor seating is available. They’re open Tuesday through Saturday.
Terri Buseman, Your Chicago Expert
Going the extra mile for my clients might mean a little less time to enjoy a glass of good wine, but finding forever homes for people who love this town as much as I do is my passion. Chicago’s wine bars are just one amazing part of the rich experience the city has to offer. There’s so much to do, choosing where to start can be overwhelming! I’m always available to help you get oriented as you explore. Contact me anytime!