Best Wine Bars in Chicago
Four of the 13 bars on this list are in Logan Square, more than any other neighborhood. Websters Wine Bar is the European-style room there, with 500 or more wines by the bottle. Easy Does It, Bungalow by Middle Brow and Common Decency are the other Logan Square bars on the page.
Other styles on the page are specific. Apero Chicago in North Center pours biodynamic bottles, including orange and skin-contact wines from Jura and Georgia. Taxim in Wicker Park keeps an all-Greek list. Bistro Monadnock in Chicago Loop keeps a 100-bottle French list. Good Funk in the Loop and Printers Row Wine Shop in South Loop focus on natural wine.
How this list is chosen: Bars with a deep wine list, a Wine Spectator Restaurant Award or a natural-wine focus, listed alphabetically. Updated October 8, 2026.
Anfora Wine Merchants
A wine retailer operating just west of Chicago in Oak Park, Anfora Wine Merchants draws visitors who have moved beyond the standard suburban bottle shop. The selection skews toward interesting, less-traveled producers rather than the predictable shelf-fillers that dominate big-box retail. For anyone making the short trip from the city, it represents a meaningful detour into a different kind of wine culture.
Apero Chicago
Deep wine list
A French-inflected café and bar on Lincoln Avenue, Apero Chicago earns its name from the European tradition of the pre-dinner drink: something unhurried, convivial, and purposefully placed before the main event. The afternoon light hits the room in a way that makes 4:30 pm feel like the only rational time to arrive, though the case for any hour holds up well.
Bar Bambi
Bar Bambi occupies a West Town address on Chicago Avenue, where the bar food programme earns as much attention as the drinks list. The format sits inside Chicago's broader shift toward bars where the kitchen is a genuine co-lead rather than an afterthought. It draws a crowd that arrives early and stays through the late hours of a Chicago winter night.
Bistro Monadnock
Deep wine list
Situated on South Federal Street in Chicago's Loop, Bistro Monadnock occupies one of the city's most historically charged blocks, steps from the landmark Monadnock Building. The bistro format in this corridor draws on a long tradition of feeding the professional midday crowd with something more considered than cafeteria speed. For visitors moving through the Loop, it represents a useful reference point in a neighbourhood not always well-served by evening dining options.
Bungalow by Middle Brow
A brewpub-rooted bar and restaurant on West Armitage Avenue, Bungalow by Middle Brow operates at the intersection of Logan Square craft culture and serious hospitality. The format rewards neighbourhood regulars and first-time visitors alike, sitting comfortably within Chicago's broader shift toward program-led neighbourhood drinking rather than destination-bar spectacle.
Common Decency
On a stretch of Diversey that runs through Logan Square's westward sprawl, Common Decency occupies the kind of address that rewards the committed rather than the casual. The bar sits in a neighbourhood where local identity and global technique increasingly share the same counter, a positioning that defines what Chicago's more considered drinking culture looks like in 2024.
Easy Does It
A Logan Square neighborhood bar on Milwaukee Avenue that trades the standard dive-bar well lineup for a carefully assembled spirits collection, without sacrificing the sociable, unpretentious energy that makes the format work. Live music from local bands, friendly bar staff, and a back bar that rewards closer inspection place Easy Does It in a distinct tier among Chicago's more relaxed drinking rooms.
Fiya
Fiya sits on North Clark Street in Andersonville, Chicago's most quietly serious dining corridor above the tourist circuit. The address alone signals intent: this is a neighborhood that rewards specificity over spectacle. Expect a program built around sourcing and fire, positioned in a local tier that prizes ingredient transparency over celebrity cachet.
Good Funk
A polished natural wine bar on the ground floor of downtown Chicago's financial district, Good Funk pitches itself at the growing cohort of drinkers who want something alive in the glass rather than corrected and cleaned. The address on North Wacker puts it squarely in pre- and post-dinner territory, and the mood tilts toward accessible rather than austere, a useful distinction in a city where natural wine can sometimes take itself too seriously.
Printers Row Wine Shop
South Loop's Printers Row neighbourhood doesn't draw the same bar-crawl traffic as River North or the West Loop, which is precisely why this wine shop has become a quiet anchor for the area. A deliberate step away from downtown Chicago's more performative drinking culture, Printers Row Wine Shop operates as a neighbourhood-scale respite built for the kind of drinking that requires focus rather than spectacle.
Taxim
Deep wine list
On Milwaukee Avenue in the heart of Wicker Park, Taxim brings Eastern Mediterranean drinking culture to one of Chicago's most restless bar corridors. The program draws from Greek, Turkish, and Levantine traditions, placing it in a distinct niche within Chicago's cocktail scene. It is the kind of bar that rewards curiosity over familiarity.
The Alley Cat
On West Division Street in Wicker Park, The Alley Cat occupies the lower end of Chicago's bar-snack format, where the drink comes first and the food follows its logic. The address puts it squarely in a neighbourhood that has cycled through several generations of bar culture, making it a useful reference point for understanding how the city's casual drinking scene continues to evolve on the Northwest Side.
Websters Wine Bar
Deep wine list
Few wine bars in Chicago carry the institutional weight of Webster's Wine Bar, which has held its corner on Milwaukee Avenue in Logan Square for nearly three decades. A regular schedule of public tasting events and a fiercely loyal local following define its character more than any single pour. For wine drinkers who want depth over spectacle, it remains a fixed point in the city's drinking culture.
Planning wine bars in Chicago
- Which neighborhood has the most wine bars on this list?
- Logan Square has four of the 13 wine bars on this list. The four are Websters Wine Bar, Easy Does It, Bungalow by Middle Brow and Common Decency. Wicker Park has the next group, Taxim and The Alley Cat. The remaining bars are single rooms in the Loop, Oak Park, South Loop, North Center, West Town, Andersonville and Chicago Loop.
- What do the bars on this list pour?
- The bars on this list pour natural wine, conventional wine, or both, and a few state a regional focus. Apero Chicago in North Center specializes in biodynamic wines, including orange and skin-contact bottles from Jura and Georgia. Taxim in Wicker Park keeps an all-Greek list. Bistro Monadnock in Chicago Loop keeps a 100-bottle French list. Websters Wine Bar in Logan Square covers rare regions alongside French and Italian bottles.
- Which bar has the largest by-the-bottle selection?
- Websters Wine Bar in Logan Square has the largest by-the-bottle selection on this list, with 500 or more wines by the bottle and 40 or more by the glass, covering rare regions alongside French and Italian bottles. Bistro Monadnock in Chicago Loop has a 100-bottle French list selected by Johnny Besch.