The guide to the 22 best wine bars in Chicago 2026
Fun, playful and modern, or classic and old-school? Whatever you prefer, Chicago has plenty for everyone. Here, Star Wine List's ambassador Torrence O'Haire has selected his favourite wine bars in the city.
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![John’s Food and Wine, a restaurant and wine bar in Chicago, USA.]()
Address: 2114 North Halsted Street, Chicago
One of Chicago’s newest wine darlings, John’s Food and Wine has become a hotspot for oenophiles and gastronomes alike. This no-reservations counter-service charmer excels at balancing fine-dining (from a Michelin-accredited chef) with a relaxed neighbourhood vibe. The warm, personal hospitality is more like one would expect from a corner pub than somewhere with such top-notch modern cuisine and a stellar wine list. That list excels both in pedigree and wine nerdery – plus the tongue-in-cheek bonus of its clever design and Jungian descriptive prose.
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![Chef's Special Cocktail Bar, a restaurant in Chicago, USA.]()
Phone: +1 (773) 666-5143
Address: 2165 North Western Avenue, Chicago
The food alone has had me obsessed with Chef’s Special for a long while. Based on a classic 70s era Chinese-American cocktail lounge, they have a special skill in creating classic Chinese-American ‘take-out’ dishes, obsessively from scratch, with fresh ingredients and a chef-driven skill but no fuss and no frills. It’s to die for. The concise wine list is a standout success, especially considering Asian restaurants aren’t often known for extensive wine programs unless you’re looking for a certain level of fine dining. To combine a fun, casual vibe with a thoughtful, serious wine list that wo...
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![Anfora Wine Merchants, a wine bar in Chicago, USA.]()
Phone: +1 (708) 613-5388
Address: 128 South Marion Street, Oak Park
If you find yourself just west of the city, Oak Park boasts an exceptional wine destination in Anfora Wine Merchants. A wine retailer first and foremost, with a great selection of interesting bottles that clearly convey the owner’s passion for Italy and the Mediterranean. Owner Adrian is a great resource for information and recommendations and, for those local to the area, their wine club is sine qua non. The best part of Anfora is the sidewalk, lined with cute tables where you can order a glass at their casual wine bar, or even pop a lucky-find bottle and lounge on the charming downtown Oak...
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![Bronzeville Winery, a wine bar and restaurant in Chicago, USA.]()
Phone: +1 (872) 244-7065
Address: 4420 South Cottage Grove Avenue, Chicago
In recent years, Bronzeville has truly made some strides in community development in the arts, culture, and food. One of the banner-holders in the revitalisation of what’s becoming a very cool Chicago neighbourhood is Bronzeville Winery, championed by a true power team in Cecilia Cuff and Eric Williams. The restaurant and wine bar works intensely in community development, working as a non-profit to support careers for women and minorities in hospitality, as well as supporting local arts initiatives and musicians with regular events. The wine list continues this ethos, featuring women- and bl...
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![Printers Row Wine Shop, a wine bar in Chicago, USA.]()
Phone: (312) 663-9314
Address: 719 South Dearborn Street, Chicago
Printers Row Wine Shop is an absolute respite from the downtown fuss and hubbub. Whether you’re escaping from a West Loop office building for the day, stealing a break between events at a convention, or taking an hour for yourself before (or after) dinner at one of the “premier” restaurants in that part of town, Printers Row acts as the perfect excuse to linger a while in conversation at the bar, or people-watch with a glass of some cool Serbian orange wine on the patio. An interesting rotating list that leans both natural and Eastern European, plus solid snacks and an inexpensive sidecar of...
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![Easy Does It, a wine bar in Chicago, USA.]()
Address: 2354 North Milwaukee Avenue, Chicago
Picture the idyllic Chicago-style neighbourhood dive bar, complete with a fun and friendly bartender and the occasional set from a local band. Now swap the menu of cheap booze and popcorn for an unpretentious and interesting array of natural wines, fun cocktails, local beer, and a super-hip bottle list for both drinking in-house and retail. Add some great music and a schedule of wine events featuring the who’s-who of both the Chicago wine scene and the modernist wine movement (plus a regular oyster-shucking pop-up), and you’ve got your social calendar booked for the month at Easy Does It....
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![Le Midi, a wine bar in Chicago, USA.]()
Phone: +1 (773) 303-4884
Address: 2108 West Division Street, Chicago
One of the best cultural practices about Chicago is the afternoon “neighbourhood wander” – find an area, often with a morning farmers’ market or afternoon street festival, stop in a local shop or two, walk around until you’re thirsty, and then discover just how skilled Chicago has gotten in providing exceptional ways to slake that afternoon thirst. One of my personal favourite oases is Wicker Park’s Le Midi. This is a picture-perfect French bar à vins, complete with a retail shop of excellent pedigree, and a constantly rotating list of seasonal wines and cocktails to enjoy on their charming...
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![Tre Dita, a restaurant and wine bar in Chicago, USA.]()
Phone: +1 (312) 725-1724
Address: The St Regis Hotel, 401 East Wacker Drive, Chicago
Tucked into The St. Regis hotel on the river in downtown Chicago, Tre Dita is a sparkly bauble adorning the shortlist of high-end downtown dining options – and sparkly it is, for certain. From the dramatic entrance to the stunning view, to the absolute glam of the bar and lounge area, Tre Dita is not a place to arrive in casual dress – so lean into it and have fun. Their white-jacketed bar team is exceptional, their service staff perfectly professional, and their menu of fine Italian dishes bucks tradition for sheer luxury. The wine list is triumphant for size alone but, under W...
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![A Beautiful Rind, a restaurant and wine bar in Chicago, USA.]()
Phone: +1 (312) 300-4535
Address: 2211 North Milwaukee Avenue, Chicago
What fortune it is for us that the best cheese shop in Chicago also happens to be a fantastic wine bar and café, at which one can easily lounge oneself into a health condition by spending hours alternating Brillat-Savarin with Vin de Savoie – truly a place of the best kinds of indulgence (provided you’re not dairy-avoiding). A Beautiful Rind’s food menu is expectedly geared toward exceptional cheese and charcuterie, with a great selection of conservas (tinned fish), pickles, and similar offerings. In addition, they have a selection of thoughtful sandwiches, plus a great happy hour where...
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![Pompette Chicago, a restaurant and wine bar in Chicago, USA.]()
Phone: +1 (773) 799-8072
Address: 1960 North Damen Avenue, Chicago
As someone who enjoys cooking for himself on the regular, living in a city with hundreds of incredible dining options to choose from on the occasion I don’t feel like cooking, it takes a pretty special spot for me to visit routinely. Pompette is that spot. The words ‘charming neighbourhood gem’ seem twee and insincere when you recognise the thoughtfulness that went into putting together something so impeccably curated that one simply enjoys being there. The food is both precise and relaxed, with balanced, modern flavours that absolutely beg for wine pairing. The wine list is clever and co...
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![J9 Wine Bar, a wine bar in Chicago, USA.]()
Phone: +1 (312) 982-2488
Address: 1961 North Halsted Street, Chicago
J9 Wine Bar is a great oasis in a neighbourhood that can sometimes trend toward ‘fluff’ restaurants, with more style than substance. A friendly, low-key vibe at their long dark wooden bar welcomes you to a well-priced menu of primarily glass pours with a ‘little bit of everything’ feel. It’s not easy to put together a list on which just about anyone can find something to love, but J9 does so effectively, and in a way that doesn’t feel cluttered or random. Their service staff is friendly and knowledgeable, further inspiring the casual comfort of the space. Stop by the botanical conservatory...
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![Volo Wine Bar, a restaurant and wine bar in Chicago, USA.]()
Phone: +1 (773) 348-4600
Address: 2008 West Roscoe Street, Chicago
Everyone loves a great neighborhood bar, and one of my favorites happens to be the excellent low-key wine bar Volo, in Roscoe Village on the northwest side of downtown Chicago. For starters, anywhere that has a $1-oyster happy hour is already a prime target on my list, and if I can drink bargain-priced Pol Roger while I drown myself in bivalves, I’ll be a regular for sure. Volo’s low-key neighborhood charm is complimented by a friendly staff, a concise and clearly wine-pairing-focused food menu, and a generous and often-changing by-the-glass list. The beverage program is rooted in an excel...
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![Good Funk, a wine bar in Chicago, USA.]()
Phone: +1 (312) 929-3185
Address: 180 North Wacker Drive, Chicago
Sailing in on the current of the natural wine trend, Good Funk’s shiny downtown wine bar is a fun stop before/after dinner, or a perfect escape from your downtown hotel if you’re into the “funky” stuff, or curious about this whole “Natural Wine” thing. I have to begin with a disclaimer: on the best days I’m a natural-wine skeptic, on my moodier days, I’m practically an antagonist. That said, I was successfully charmed by the clever snacks and interesting wine list that is indeed really hipster, but is thoughtfully curated in such a manner that it welcomes wine nerds of all persuasions - from...
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![Apero Chicago, a wine bar in Chicago, USA.]()
Address: 4160 North Lincoln Avenue, Chicago
Apero is pure joy at 4:30 in the afternoon. Anytime, really, but to name one’s café after the golden hour would indicate the best time of arrival, wouldn’t you think? Truly, Apero has the most French vibe of any spot in Chicago, as far as I’m concerned. The light food menu is modern and nonspecifically (but deliciously) Euro-chic, the wine list is global, but the vibe is instantly and impeccably French. A young, hip crowd lounges on the patio, drinking vermouth and burrowing through happy-hour-oysters like a walrus and/or carpenter - stylish yet unstuffy, you’ll be ready to light a Gauloise...
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![Websters Wine Bar, a wine bar in Chicago, USA.]()
Phone: +1 (773) 292-9463
Address: 2601 North Milwaukee Avenue, Chicago
Webster’s Wine Bar is a nearly 30-year-old institution in the Chicago wine scene, holding down its busy corner in Logan Square with devoted regulars and many popular public wine tasting events. They tout their expertise on “natural and minimal-intervention wines,” as is a trend in wine bars right now, and their generous glass-pour list leans heavily into the crunchy and funky with obvious passion. Their bottle list is broad and similarly creative, with a true dedication to appeasing the most intense wine nerds; 1993 Chinon Blanc, anyone? The food menu is concise and well-appointed to pair wit...
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![Lush, a wine bar and restaurant in Chicago, USA.]()
Phone: (773) 281-8888
Address: 2232 West Roscoe Street, Chicago
Originally a local-darling of a wine shop started 20 years ago, Lush has since evolved into a tasting room/wine bar/bistro with three locations and a dedicated following of passionate partakers. The Roscoe Village wine retail room is a veritable theme park of bottles of all levels, price points, and rarity (all of which are drinkable on-site with a minor corkage fee), and the large bar area and pretty patio offer guests a great spot to sit and wax poetic about the world of wine. The menu offers a wide range of fairly classic (but great quality) glass pours, with an open array of flight optio...
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![Rootstock, a wine bar and restaurant in Chicago, USA.]()
Phone: +1(773) 292-1616
Address: 954 North California Avenue, Chicago
A quick stop west of downtown, one of the gems in the Humboldt Park neighborhood is this long-standing wine bar with a massive local following. The vibe is exactly what a cozy neighborhood hole-in-the-wall should be, with dim lighting, low ceilings, and significant kitsch-factor in the decor, but the menu is anything but ordinary. The wine program leans into the trendy “natural wine” movement but without dogma or pretention. A generous list of crunchy options highlighting the bar’s nerd-chic style - Jura, Basque cider, sherry, orange wine, and ancestral method sparklers all share strong place...
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![All Together Now, a wine bar and restaurant in Chicago, USA.]()
Phone: +1 (773) 661-1599
Address: 2119 West Chicago Avenue, Chicago
All Together Now is a fun neighborhood spot that does an excellent job acting as both retail (a funky wine shop and carryout deli/fromagerie) and bistro, with a fresh, modern menu of great sandwiches, vegetable-heavy small plates, and some of my favorite cheese-and-charcuterie boards in the city. The well-priced wine program invites exploration: they offer a creative glass-pour list, and for a very reasonable $10 to $ 15 corkage fee, they’ll serve any of the 150 bottle options they offer in their wine shop. They feature predominantly modernist (some might say verging on “hipster”) wines, with...
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![Table, Donkey and Stick, a wine bar and restaurant in Chicago, USA.]()
Phone: +1 (773) 486-8525
Address: 2728 West Armitage Avenue, Chicago
I’ll try to write this as professionally as I’m able, because I adore Table, Donkey, and Stick. Consider even that the subtitle of this small, rustic bistro & wine bar is “crusty bread, brandy, fire” - how could it not be exceptional? Table, Donkey, and Stick is tucked into the Logan Square neighborhood, a short jaunt from downtown Chicago (and a fun area for trendy new food and drink options). Their menu is gently alpine-themed, with an excellent selection of cheeses and charcuterie, and a regularly changing array of small plates. A few (very delicious) entrées are on offer, but the menu cle...
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![Pops for Champagne, a wine bar and restaurant in Chicago, USA.]()
Phone: +! 3122667677
Address: 601 North State Street, Chicago
40 years of popping bottles has enshrined Pops for Champagne with a title of “Chicago standard,” undoubtedly. Situated on a busy corner in the heart of downtown Chicago’s shopping district, visitors are delighted to find a charming, unpretentious (though clearly high-end) champagne bar that speaks directly to locals and wine nerds, not just crowds of tourists. Boasting one of the best champagne collections I’ve ever seen, one is invited to dive as deeply into sparkling-wine-obsession as their interest (and pocketbook) allows. The atmosphere is comfortable, the staff knowledgable and welcomin...
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![Alpana, a wine bar and restaurant in Chicago, USA.]()
Phone: +1 (312) 624-8055
Address: 831 North State Street, Chicago
The newest restaurant from local Master Sommelier Alpana Singh, Alpana is a beautifully designed dinner spot in Chicago’s glamorous Gold Coast. Take a seat at the gorgeous bar or book a table and enjoy a creative menu of globally influenced, Italian-inspired cuisine, with options like tagliatelle and romesco sauce or “butter chicken meatballs” - both delicious. Earning my “best wine-list writing” award (for what it’s worth), the wine list truly shines, demonstrating wine director Singh’s expertise, as well as the skill of her team. Each wine is well-described in a concise, welcoming blurb th...
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![Acanto Wine Bar, a restaurant and wine bar in Chicago, USA.]()
Phone: +1 (312) 578-0763
Address: 18 South Michigan Avenue, Chicago
On the main Millenium Park drag in downtown Chicago, things can get eye-rollingly touristy pretty quickly. But, in a desert of chain restaurants, deep-dish pizza, and food-truck hot dogs, a cozy, charmingly Italianate, upscale wine bar like Acanto is an oasis. Honor dictates that I disclose this restaurant is a part of the group I work for personally, but it’s also the restaurant I visit the most in my free time, so reader, take that as you will. With a bustling downtown clientele, Acanto’s buzz in their dimly lit dining room, their direct-from-Milan marble bar, or their lush sidewalk patio...
