Food & Drink

The Best Wine Bars in Chicago

Published On 02/22/2016 Published On 02/22/2016
Enolo Wine Cafe, Wine Bar, wine, bar
Courtesy of Enolo Wine Café
Courtesy of Webster’s Wine Bar

Webster’s Wine Bar

Logan Square

One of the city’s most beloved wine bars may have recently relocated from Lincoln Park to the former Telegraph space in Logan Square, but that hasn’t stopped its ridiculously knowledgeable and well-traveled staff from uncorking a massive 500+ bottle-deep selection of global wines in a European-style setting whose bookshelf bar serves as its main focus. Nosh on venison tartare and duck mac and cheese or stop in for tasting events like “The Heavy Hitters of Tuscany.” We’re not sure how hard the folks at the Wall Street Journal party, but they named Webster’s one of the top five wine bars in the US, so surely that counts for something.


Humboldt Park

This cozy but oft-overlooked little space opened by three former Webster’s Wine Bar employees specializes in small-batch wines and beers with an emphasis on organic farming. In addition to the standard French and Italian wines, they are pouring palate-pleasing varietals from South Africa to Slovenia in addition to an unusually heavy Greek and German contingent. They’ve also got Moody Tongue Caramelized Chocolate Churro Baltic porter, a deliciously under-the-radar dry-aged Slagel Family Farm burger and a Sunday brunch where you can order bratwurst. So what the hell are you waiting for?

Courtesy of Eno Magnificent Mile


Mag Mile

Located in the Mag Mile’s towering InterContinental Chicago, this sexy spot offers a darker lounge vibe evoking an intimate wine cellar where you can go ape all over their award-winning wines and international menu of cheeses. Bonus 1) a wine flight named Games of Rhones. Bonus 2) Chocolate-dipped bacon they call Chicago Dinner. Still don’t know shit about wine? Enroll in their ENOversity for monthly courses on things like Wines Down Under. With tastings, of course.

Courtesy of D.O.C Wine bar

DOC Wine Bar

Lincoln Park

No, DOC does not stand for District of Columbia. It’s the acronym for Italy’s Denominazione di Origine Controllata, or the geographic area of production for each wine in the country. But it’s not just Italian wines we’re talking about at DOC -- it’s everything from Napa Valley magnum bottles to “Pino Envy” global wine flights to sip by the fireplace beneath a cool wood-beamed ceiling. Stop by Monday nights for 50% off bottles under $100 and grab some avocado fries, lobster deviled eggs, and mini filet sliders while you’re at it.

Courtesy of Vera


West Loop

Tucked underneath the el tracks is this laid-back, approachable little joint specializing in Spanish wines and Spanish-infused small plates like bocadilla sandwiches and chicken thigh chilindron. The friendly staff will have you feeling at home as they guide you through flights of sherry and tapas in the simple dining/tasting room. If nothing else, it’s the perfect place to impress a date with all that worldly knowledge you supposedly amassed during that semester you spent “studying” in Barcelona.

The Twisted Vine


A few years ago this cheery little Boystown space transitioned from a wine shop to a lounge-style bar where you can explore some of the finest wines and whiskeys in the area. Probably best known for regular jazz and piano live music acts, it remains a mellow, never-too-crowded space of candles and chandeliers where -- if you’re not into music -- you can also pair your wine with popcorn during movie night screenings of films such as Moulin Rogue! and Cabaret. So in that sense, it’s kind of like Brew & View. Only with wine. And not at all like Brew & View.

Courtesy of Volo


Roscoe Village

A wine bar is not necessarily the first thing that comes to mind when you want a night out “on the cheap,” but Volo is working hard to change all that with a dozen food items priced between $4-$12 and 20 bottles $45 or less. They’re all about accessible boutique wines here, not to mention house-made sangria and pork belly on a stick. Volo also houses one of the city’s best under-the-radar patios, now heated with a retractable awning.

BIN 36

BIN 36

West Loop

In contrast to the typical little wine bar down the corner, BIN 36 feels like the big boy on the block with a larger space featuring everything from cork-topped tables and table-side mixology to cold-dripped sangria and mimosa flights. But despite its more “mainstream” environs, Bin 36 manages to keep things warm and intimate thanks in no small part to its friendly and engaged owner Enoch. They also have a full dinner menu including pork chops and strip loin plus wine classes in cheese/food pairings. Also, there’s a wine shop where you can order their wines online. Handy, no?

Ampersand Wine Bar


One of the best openings of last spring serves a notable brunch to boot in a bright, inviting space that’s totally modern yet totally unpretentious. Sign up for their wine club for a monthly wine allowance of one to three bottles plus tickets to exclusive wine dinners, or stop by nearby Groundswell CafĂ© during monthly Ampersand comfort food pop-ups for your chili/mac and cheese fix.

Courtesy of 404 Wine Bar

404 Wine Bar


Brought to you by Big Onion Tavern Group (Fatpour, Derby, Irish Oak, etc), 404 eschews the bro culture you might expect with a sophisticated space of reclaimed wood, leather sofas, and salvaged lighting. Belly up to the fireplace to run through their solid selection of seasonal wines or mingle with neighbors during monthly “Neighborhood Night” events. There’s blackened shrimp sliders and tenderloin tacos if you’re hungry and, if you’re still thirsty, you take your wine with you thanks to the bar’s clutch “cork and carry” license. Bring some home for the bros.

Courtesy of Enolo Wine Cafe

Enolo Wine Café

River North

The sparkling River North environs of Enolo Wine Café is the last place you would expect happy hour specials of pork rinds and fried goat cheese. Yet there they are, beckoning you besides a progressive 25-bottle wine list designed to make your introduction to wine culture as painless as possible. There’s also wine flights, a wine club, and wine bottles to go. So yeah, pretty much everything you need in a wine bar. And if you feel like getting all bougie and sniffing your wine for 20 minutes before daring to take a sip, no one’s going to judge you (out loud).

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1. Webster Wine Bar 2601 North Milwaukee Ave, Chicago, IL 60647

Here's the scoop: The original was in Lincoln Park, but then the owners decided to close it, re-concept their Logan Square spot Telegraph, and reopen it as the current iteration of Webster Wine Bar (which, subsequently, is no longer on Webster St.). But with a wine list 500 deep, it's an institution wherever it's located.

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2. Rootstock Wine & Beer Bar 954 N California Ave, Chicago, IL 773.292.1616

Opening today from a group of Webster's Wine Bar vets aiming to achieve simultaneous vino and brew notoriety, RS's a cozy 50-seat nook decked out with locally painted artwork and mismatched, second-hand furniture.

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3. ENO 505 N Michigan Ave, Chicago, IL 60611

A top-notch date spot, ENO wine bar boasts a cozy aquarium fireplace and varied menu that will impress anyone who’s into wine, cheese, or chocolate. And if your date isn’t into wine, cheese, or chocolate, it might be time to find a new one.

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4. D.O.C. Wine Bar 2602 N Clark St, Chicago, IL 60614

Fun, quaint, and comfortable would be three words to describe this cozy little vino spot. Wine lover or not, this is a good place to try a flight of alcoholic grape juice from international selections with zero intimidation factor. Pair the fine selection of Italian reds and French whites with crispy avocado fries, bruschetta, and, of course, cheese to soak everything up.

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5. Vera 1023 W Lake St, Chicago, IL 60607

This Spanish-leaning wine bar offers seasonally rotating vinos alongside shareable plates like bacon-wrapped dates, ceviche, paella, and charcuterie.

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6. The Twisted Vine 3530 N Halsted St, Chicago, IL 60657

The Twisted Vine is one of our favorite wine bars in Chicago thanks to their perfect wine menu and live music nights. If you're not into live music, keep an eye out for their movie night events, where you can create your own wine and popcorn pairings to chow down on during some great movies.

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7. Volo Restaurant Wine Bar 2008 W Roscoe St, Chicago, IL 60618

There are plenty of reasons to love Volo Wine Bar, but we would say the number one reason would be the wine prices. We love how cheap the wine is, as well as how delicious their food is and how cozy and upscale their atmosphere is. They also have a heated patio with a retractable awning so you need to get here now.

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8. Bin 36 161 N Jefferson St, Chicago, IL 60661

Bin 36 is one of the biggest wine bars in the area, and it deserves your undivided attention. They have a delicious dinner menu and an extensive wine list, as well as sangria and mimosa flights. Make sure to sign up for one of their wine pairing classes if you want to take your Bin 36 experience to the next level.

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9. Ampersand Wine Bar 4845 N Damen Ave, Chicago, IL 60640

Without pretentiousness, Ampersand Wine Bar is bursting with outstanding wines and globally inspired comestibles. The atmosphere is casual and the food (which includes burrata with duck prosciutto and arugula, Calabrian pork cheek with pearl onion agrodolce and heirloom tomato, and roasted asparagus with salsa verde) will keep you satiated well into the next bottle.

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10. 404 Wine Bar 2852 N Southport Ave, Chicago, IL 60657

Everything about this place, from their chic fireplaces to their extensive wine list, screams sophistication. 404 Wine Bar is the perfect place to bring a date that you are really looking to impress, and their dinner menu is out of this world. Make sure to be on the look out for their awesome upcoming events.

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11. Enolo Wine Cafe 450 N Clark St, Chicago, IL 60654

Enolo Wine Cafe is one of our favorite wine bars in Chicago, and you need to go and check it out. Besides their awesome and extensive wine list, they have great happy hour deals featuring oddball bar foods like pork rinds and fried goat cheese. This is a great place to consider if you are looking to really impress a date.