Chicagoans are known for having strong opinions about their beloved city—and that includes a deep pride in the neighborhoods they call home. Nowhere is this loyalty more evident than in the Near West Side’s Ukrainian Village. Since the late 19th century, Ukrainian immigrants have built up this enclave, which spans several blocks, into what it is today. And any gentrification that has occurred hasn’t dimmed the neighborhood’s Ukrainian pride one bit.

Chicagoans have embraced the ‘hood even more since Russia’s invasion of Ukraine in 2022, sparking a war that sadly continues to this day. Whether you’re Ukrainian or not, you’ll feel the electric energy of the neighborhood—blue and yellow pride is visible everywhere. There’s something undeniably satisfying about the universal support locals show for its bakeries, museums, cathedrals, and even parades.

The area’s diverse restaurant and bar scene has seamlessly integrated into the fabric of the neighborhood. Ukie Village, as the locals call it, is home to a gorgeous Filipino tasting menu at Kasama, some of the best Thai restaurants around (JJ Thai Street Food and Silli Kori), and the 10-year-old institution Boeufhaus, one of Chicago’s best steakhouses. Wine lovers will find classic French-inspired spots, natural wine havens, the city’s most comprehensive South American list, and yes, even a chance to explore Ukrainian wines. Below is an incomplete but fantastic list of some of our favorite wine-fueled spots.

Le Midi

You know that sinking feeling when a place you love changes hands, and you brace for the inevitable letdown? Le Midi avoided that entirely when it took over the Joe’s Wine Cellar space (which was wonderful in its own right). A wine bar/wine shop hybrid, Le Midi wholeheartedly brings the concept of l’heure de l’apéro (aperitif hour) to Division Street, the entertainment capital of Ukie Village. First-time guests quickly find themselves feeling like Norm from Cheers because of the welcoming envorinment. It turns out the neighborhood needed a spot for the very French tradition of unwinding with a glass of wine—or three—and some small bites before or after dinner.

The petiscos and pintxos are delicious and simply executed, perfectly complementing the dynamic list of wines by the glass. Sometimes, wine lists at restaurants in a city can feel too similar to one another, but not here. Thanks to Portuguese wine enthusiast Craig Perman, owner of Perman Wine Selections and a partner at Le Midi, the list leans heavily on bottles from that country. You’ll also find Stellenbosch and Sicilian whites, a gulpable Côtes du Rhône, and possibly Kiràlyudvar’s Hungarian Furmint-Hárslevelü blend.

The vibe of the space screams first date, with a remodel that blends flirtatious and sexy energy. But don’t let that stop you if you’re unattached—groups and solo visitors alike effortlessly fit into the scene. Managing Partner Seth Wilson holds court at a communal table in the back, hosting tastings and events that feel more like gatherings of old friends than any formal affair.

Brasero

Chef John Manion is well known for his downtown Argentinian steakhouse, El Che, but his newer venture, Brasero, continues that restaurant’s South American tradition with a focus on Brazilian cuisine. The lively scene features an open kitchen and an enormous full-service bar, with warm-hued, textured decor and impeccable lighting—creating an inviting space you’ll want to linger in, even after dinner.

Alex Cuper, Wine Director at both spots, decided early on that he and Chef Manion would work toward having the greatest South American wine list in the nation—and they’ve arguably achieved it. Chicagoans can expand their knowledge of South American wine and dive deep into different varietals from the continent, thanks to the team’s tireless pursuit of family-owned, socially and environmentally conscious producers.

Brasero has a list of 100 wines, all under $100, with names like Ana María Cumsille from Chile’s Itata Valley. Her Aguila is one of 14 wines in the list’s dedicated País section (“País could not be more perfect for our cuisine,” says Cuper). Expect to find everything from Riesling and Chenin Blanc to Syrah, Cabernet Franc, and, of course, Malbec.

All Together Now

For natural wine lovers, this funky, all-day cafe is a no-brainer. The retail wall is intentionally curated—every bottle seems to have its place, whether for a specific occasion or pairing. If you’re not sure what to choose, the exceptionally friendly staff is always happy to drop some wine knowledge, all without a hint of pretension.

All Together Now opens for brunch (insider tip: they bake their own delicious bagels every weekend) and naturally evolves into a cozy evening hangout. By-the-glass pricing is modest, ranging from $10 to $16, and the offerings are both focused and thoughtful. You’ll find Slovenian Pet Nat Rosé next to a renowned Prosecco producer, Italian giants like Foradori alongside Columbia Valley Mourvèdre, and whimsical field blends like Mendocino’s Pink Lemonade from Emme Wines. Whether you hit up their cheese counter, cozy up to the bar, or grab one of the coveted patio tables, this might be the breeziest joint in Ukrainian Village.

Rootstock Wine & Beer Bar

Rootstock is actually just over the border in Humboldt Park, but no list of great wine destinations in the area would be complete without mentioning it. Since 2009, Rootstock has been the neighborhood’s favorite natural wine bar. Owners Jamie McLennan and Johnny Hap (two-thirds of the founding group) lead one of the loveliest teams in the city.

The vibe here? Cozy neighborhood chic—low lighting, mismatched furniture, and rotating local artwork on the walls. McLennan’s artful curation of the wine list means you’ll hardly notice you’re in a natural wine bar. Ancestrale Method sparklers sit comfortably next to Grower Champagne, and monumental Burgundy producers share space with wines from Jura and Arbois. The universal takeaway? McLennan loves acidity, which pairs perfectly with the outstanding food menu, much of which is sourced from local farmers. Stop by for a glass or two, but don’t leave without trying the 28-day dry-aged Slagel Farms burger—one of the best in the city.

Tryzub Ukrainian Kitchen

While not entirely wine-focused, no tour of Ukrainian Village’s iconic drinking spots would be complete without a stop at Tryzub. Opened in 2014, just after Russia invaded and annexed Crimea, Tryzub is a neighborhood staple that has supported Ukraine through community fundraising. The space itself is colorful, eclectic, and filled with Ukrainian art and history. While it’s hard to pass up the whimsical “Wheel of Fun” (a tabletop Ferris wheel with eight house-infused spirits), the wine list is thoughtful, food-friendly, and includes several well-chosen Ukrainian bottles.

Explore the country’s sparkling side with a Sekt made from the indigenous Chersegi grape, or taste the Carpathian Mountains’ volcanic soils through some of their choice whites. Come for a bowl of goulash paired with Chateau Chizay’s red blend (Cab Sauv and Merlot), stay for the intense feelings of pride and support you’ll inevitably feel... and maybe a shot of horseradish-infused vodka.