Chicago's wine scene runs from Logan Square's pioneering Webster's Wine Bar to River North's glittering Pops for Champagne and Bronzeville Winery, the South Side's Black-owned destination for food and vino. Whether you want funky natural pours, a 500-bottle cellar or a DJ-backed Sunday brunch, this city pours it all.
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Black-owned wine destination anchoring 44th and Cottage Grove, spotlighting winemakers of color alongside seasonal plates, DJ sets and a buzzing Sunday brunch.
Pip’s Tip Wednesday to Sunday. Black-owned at 44th and Cottage Grove, and Sunday runs brunch then dinner with a gap between.
Opened in 2025 by husband-and-wife team Jacare Thomas and Charlette Stanton, this elevated wine and charcuterie bar champions Black winemakers and distillers across two spaces: the airy Park and speakeasy-style Manor.
Pip’s Tip Reserve through OpenTable. Jacare Thomas and Charlette Stanton opened it in 2025, so it is still the new room.
A candlelit Logan Square institution since 1994 with hundreds of organic and biodynamic labels. Weekly Wednesday flights and a full late-night kitchen.
Pip’s Tip Logan Square since 1994, candlelit. Hundreds of organic and biodynamic labels.
A beloved no-reservations neighborhood wine bar est. 2009, pairing an adventurous low-intervention bottle list with one of the city's best bar kitchens.
Pip’s Tip Neighborhood natural-wine hideout
Chicago's iconic champagne bar pours an encyclopedic list of grower Champagne and sparkling wines by the glass. Sleek circular bar, caviar service and a wine club.
Pip’s Tip Bubbles temple since 1982
An all-day cafe, bottle shop and wine bar where you can drink anything off the retail shelves with expert cheese pairings. Wine clubs, classes and tastings round it out.
Pip’s Tip Wine-and-cheese shop hybrid
A moody natural wine bar and cafe pouring skin-contact, pet-nat and low-intervention gems until late, with a second outpost in the Loop.
Pip’s Tip Natural wine, late-night funk
A Roscoe Village fixture since 2005 with boutique-producer bottles, small plates and winemaker dinners. Its lush back patio is billed as Chicago's #1 hidden patio.
Pip’s Tip Hidden garden patio pours
An intimate, no-reservations Lincoln Park wine bar pouring globe-spanning glasses from California to Romania, with cheese boards and frequent tasting events.
Pip’s Tip Cozy first-come neighborhood charmer
Part shop, part bar, with WineStation self-serve taps offering taste-to-full pours of rotating bottles, plus a full kitchen, wine club and communal tables.
Pip’s Tip Self-pour tasting stations
A chef-and-sommelier-run Lincoln Park hit whose marble bar is one of the city's best seats for by-the-glass discoveries, with a market-driven menu.
Pip’s Tip Sommelier-driven bar seats
A cheesemonger-led shop and bar near the California Blue Line pairing guided tastings and epic boards with a smart, affordable wine list.
Pip’s Tip Cheese-first wine pairing haven
Open since 1994, the granddaddy of Chicago wine bars pours organic, biodynamic and small-producer bottles from a deep, ever-rotating cellar in a candlelit Logan Square room. Wednesday night flights and a serious late-night kitchen make it the city's essential wine hang.
Wine is one chapter of Pip's Lifestyle, find the whiskey bars, lounges, steakhouses and the Domino Club below.
