Wine education in Chicago right now is flourishing. Shop owners say they are finding particular success with a multicultural approach that takes curious Chicagoans beyond traditional regions.

Here are eight destinations with a recommended course lineup.

Acanto Restaurant + Wine Bar

The Loop
18 S. Michigan Ave.

Every Wednesday, Acanto’s wine director and certified Italian wine expert Torrence O’Haire leads attendees through a guided tasting of four wines with the goal of teaching them to learn how to order, describe and understand and enjoy Italian wine with confidence. This is the fourth year of the aptly named “Learn to Speak Italian Wine” series ($45). The hour-long classes touch on geography, climate, classification systems, soil and the effects of time on wine — all through the lens of Italy’s 20 winemaking regions.

Beautiful Rind

Logan Square
2211 N. Milwaukee Ave.

This Logan Square cheese shop hosts regular wine-and-cheese pairing classes that typically cost $68, including one covering the basics of wine and cheese pairing through five wines and five cheeses, and a popular series of “wine and rind” classes that dig into places (Italy, France) and styles (natural wine).

Some of the wines and Champaigns used in recent wine tasting classes sit on a table at BottlesUp! located at 3164 N. Broadway in the Lake View neighborhood, Friday, Feb. 20, 2026.

BottlesUp! hosts a slew of in-person programming for all kinds of wine lovers.

Tyler Pasciak LaRiviere/Sun-Times

BottlesUp!

Lake View
3164 N. Broadway

Walking the walk of a community-first approach, BottlesUp! hosts a slew of in-person programming for all kinds of wine lovers. This includes the annual Run for Rosé 5K , which draws up to 150 participants; recurring events like oyster shucking; educational tastings focused on places like the Republic of Georgia; champagne study halls to make the formidable sparkler more accessible to all; and wine and dance classes, in which wines are paired with specific dances.

Bronzeville Winery at 4420 S. Cottage Grove Ave. in Bronzeville

Bronzeville Winery’s Tiered Wine Collective membership includes Just Vibes ($45), which offers access to monthly meetups (typically capped at around 50 people) that feature discussion panels, guided tastings and discounts on retail bottles.

Anthony Vazquez/Sun-Times

Bronzeville Winery

Bronzeville
4420 S. Cottage Grove Ave.

Black-owned Bronzeville Winery one-ups the monthly bottle club membership with themed programming that places said juice in a richer social, cultural and historical setting.

“I created the Wine Collective to intentionally break down barriers,” said Bronzeville Winery owner Cecilia Cuff. “Wine can feel intimidating. It can feel exclusive. I wanted to remove that distance and create a space where curiosity is welcomed. When we taste together, we talk. When we talk, we begin to understand each other. That is how connection begins.”

Tiered Wine Collective membership includes Just Vibes ($45), which offers access to monthly meetups (typically capped at around 50 people) that feature discussion panels, guided tastings and discounts on retail bottles. Memberships that include bottle selections include the Enthusiastic Collective ($75) or Luxe Collective ($125). On March 30, wine and spirits expert and author Regine Rousseau, who founded Shall We Wine, will lead a Women’s History Month tasting and discussion of four women-made wines, touching on themes of access and representation in the wine industry.

Deep Red Wine Merchant

Avondale
2901 N. Milwaukee Ave.

This hipster spot in Avondale offers quarterly Wine 101 classes, plus introductions to lesser-known regions like Hungary and the Republic of Georgia as well as pairing events. Classes typically range from $50 to $75 and max out at eight people, but the shop will actually close to the public for high-demand events such as pairing sparkling wine with potato chips (and caviar!) to accommodate its 24-person maximum. In a seeming trend, “it’s rare for us to have a class that doesn’t sell out,” said owner Dave Thompson.

Le Midi Vins & Apero

Wicker Park
2108 W. Division St.

Sprung from the whimsical mind of Le Midi co-founder and sommelier Seth Wilson, the lively classes ($55 to $100) at this Wicker Park wine bar-bottle shop hybrid lean playful and edgier. Think a blind tasting showdown of four North American wines versus four Eastern European wines with a “Heated Rivalry” theme, nodding to the relentlessly popular HBO Max show; or a tour of wines made with Bordeaux varietals outside France. “They’re a little more social, the tastings,” said co-founder Craig Perman, also of Perman Wine. “We keep Midi open during tastings, although we just put in acoustic ceiling tiles so you can hear better. They’re always playful and fun and Seth is such a professional.”

Perman Wine Selections

West Loop
1167 N. Howe St.

Open since 2007, Perman draws a loyal cohort of longtime customers to its sold-out tastings ($75 to $85) that run an hour and a half and take attendees through an eight-sample tour of classic winemaking regions, including different expressions of Spanish Rioja or Italian Sangiovese; an overview of what owner Craig Perman calls France’s vastly “underestimated” Loire region; or Grenache around the globe. Though he says tastings lean pricey, Perman has been known to pop rare delights, like a bottle of Bodegas Vega Sicilia Valbuena that might fetch $600 at a restaurant.

Wine class attendees smell and inspect wine at Uvae Kitchen & Wine Bar on Saturday, Feb. 21, 2026.

Uvae in Andersonville hosts weekly sommelier-led classes in its private dining room.

Uvae Kitchen & Wine Bar

Andersonville
5553 N. Clark St.

This Andersonville wine bar and restaurant hosts weekly sommelier-led classes in its private dining room. Offerings range from homages to female winemakers and winter whites to pinot noirs from all over the globe. Classes cost $40 and typically run for 90 minutes.

Maggie Hennessy is a Chicago-based food and drink writer whose work has appeared in The New York Times, Bon Appetit and Food & Wine. Follow her on Instagram.

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