In a city as vibrant as Chicago, it’s no surprise that the wine bar scene has flourished. These establishments not only offer a diverse selection of wines from around the globe, but they also create spaces where friendships blossom, and memorable evenings unfold. From quaint nooks with curated selections to lively venues with unique events, the city invites you to explore the world of wine in all its glory. Let’s dive in and find out the best wine spots in town.

Red & White

For over 15 years, Red & White has been the lighthouse of Chicago’s natural wine scene, leading the way with their annual Third Coast Soif natural wine fair. What started as a humble corner shop has expanded into a chic, airy wine bar, offering cheese, tinned fish, and seasonal snacks that pair perfectly with your glass of vino. Grab a killer sandwich, wander the shop, and they’ll even open anything you buy for you to sip on the spot. Now that’s customer service.

Source: WC Studio

Anelya

You might not immediately think of Ukrainian wines when planning your next outing, but Anelya is here to change that. Reimagined from the closed doors of Wherewithal, this Ukrainian American gem by James Beard Award winners Johnny Clark and Beverly Kim embraces Clark’s heritage. The wine list leans heavily on Eastern European labels, with bottles from Czechia to Georgia. Pair that with Ukrainian specialties like dumplings, noodles, and borscht, and you’re in for a culinary adventure that’s both delicious and deeply personal.

Source: Star Wine List

Monteverde

Monteverde is a beacon of modern Italian cuisine in Chicago, a spot where you can sit down and feel like you’ve stepped into a vibrant Italian piazza — minus the jetlag. The wine list? Small but mighty. It’s packed with Italian classics, but they don’t shy away from exciting new producers either. Their dishes roam the entirety of Italy, offering cool twists on regional favorites. Even if you’re an Italian food expert, Monteverde will have you saying, “Oh, that’s cool!” with every sip and bite.

Source: UChicagoBite

Deep Red Wine Merchant

Deep Red Wine Merchant is the ideal haunt for horror buffs and wine lovers alike! This Avondale gem, named after the iconic 1975 film, boasts a warm atmosphere and a wine list that highlights vintners. It’s the perfect spot for a laid-back drink or a fun night out with friends — complete with a touch of spooky flair.

Source: Block Club Chicago

Perilla

Perilla isn’t just any steakhouse — it’s a Korean-American steakhouse, and it brings some serious flavor to the Chicago scene. With locations in both the West Loop and downtown, this spot delivers expertly grilled meats, Korean classics like stews, and an eclectic drink menu that’s a joy to explore. From soju to skin-contact wines, their beverage list is as playful and adventurous as the menu. Not sure what wine pairs best with Korean BBQ? Don’t worry, their sommelier’s got you covered.

Source: Open Table

Easy Does It

Miss the crowded, dance-filled nights at East Room? Well, it’s time to make a smoother transition into adulthood with Easy Does It in Logan Square. With natural wines flowing and DJs spinning after 10 p.m. on weekends, this spot keeps the fun alive. Add in a massive outdoor patio for al fresco sipping and you’ve got the recipe for a perfect wine night. Wine tastings? Check. Laid-back vibes? Double check. Don’t be surprised if this becomes your new late-night hang.

Source: Easy Does It

J9 Wine Bar

In a world where wine bars can feel a little impersonal, J9 Wine Bar brings a refreshing dose of warmth and community. Named for owner Sonya Mlodzek’s late sister Jeanine, this Lincoln Park treasure feels like home. The wine list, curated by Johnna Battaglia, offers both nostalgic comfort wines and funky varietals for the adventurous. And if you’re feeling snacky, their charcuterie boards and potato chip pairings make the perfect partners for your glass.

Source: Star Wine List

Taxim

While not your typical wine bar, Taxim deserves a spot on this list for its killer rooftop and rustic Greek menu. Hidden away in Wicker Park, this spot serves up house-made sausages, wild fennel-filled pastries, and mastic-spiked ice cream that will transport you straight to the Mediterranean. Pair it with a crisp Greek white wine, sit back on the rooftop deck, and pretend you’re in Santorini. No passport required.

Source: Eater Chicago

Brasero

If you're looking for a creative cocktail and a killer wine list, Brasero is the place to be. Boasting a “100 under $100” South American wine menu, this spot encourages guests to try interesting, often surprising selections, like chilled Païs or Chilean skin-contact whites. It’s the kind of place where every bottle is a conversation starter — and nothing feels out of reach.

Source: Instagram

Webster’s Wine Bar

We can’t talk about wine bars in Chicago without mentioning Webster’s Wine Bar. As the OG of the scene, it’s been serving up Old World vintages for decades, first in Lincoln Park and now in Logan Square. With dim lighting, cozy vibes, and a seemingly endless wine-by-the-glass list, it’s the perfect spot for dates, hangouts, or just savoring some fermented goodness on your own.

Source: CNTraveler

So, whether you're looking for a hidden gem or a buzzing new hotspot, Chicago’s wine scene has a seat — and a glass — waiting for you. Each of these places offers something unique, from natural wine pioneers to Eastern European surprises, and everything in between. So, next time you’re in need of a pour, why not explore something new? After all, life’s too short to drink bad wine.