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Eight shops that deliver smart Wine 101 lessons in Chicago
· Updated
Maggie Hennessy rounds up local wine shops that offer some interesting lessons with a twist, like a Rosé 5K and introductions to lesser-known wine regions.
This guide was originally published on suntimes.com and wbez.org on Feb. 26, 2026.
8 places
Showing 8 of 8 places
Acanto
Salumi, pizza, pasta & other Italian fare plus cocktails & a large wine list in a relaxed setting.
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
Upscale fromagerie & charcuterie offering cheese-centric dining, plus a classroom.
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).
BottlesUp!
Neighborhood, woman-owned shop offering wine from around the world (many natural), plus beer, spirits and sake. Also monthly wine clubs.
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.
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Bronzeville Winery
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.”
Deep Red Wine Merchant
Relaxed shop for bottles featuring a curated assortment of wines from global regions.
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.
Le Midi Wine
Sleek seller of a wide range of wines by bottle or glass & craft beers, plus tastings & patio.
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
Sophisticated wine boutique stocking a range of bottles & spirits in sleek digs with a tasting room.
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.
Uvae Kitchen and Wine Bar
Stylish destination for contemporary American fare with house cocktails & a curated wine list.
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.