Chicago’s 7 Best Wine Bars

From fancy bubbly bars to chill natural wine emporiums, there’s an experience for every occasion

January 16, 2024 7:11 am
Glasses of wine and wine bottles
Victoria Shapow

Whether you’re a wine novice or an aficionado, this city has plenty of unique spots to enjoy everything from a glass of Gamay to a bottle of Barbera. Sure, you might love your go-to value bottle from the liquor store, but every now and then it’s time to step outside your comfort zone and try something new. Our picks for Chicago’s best wine bars feature experiences from casual to swanky, but overall, you’ll find it easy to fall in love with your next favorite varietal. What’s more, each locale has an equally well-curated food menu that’s bound to come in handy as you order one more pour. Read on for the seven places you should be sipping at next.

Pops For Champagne

River North

Why you’re here: You’re in a celebratory mood.

What you’re ordering: This four-decades-old bar features any and all types of sparkling by the glass and bottle in equally sparkling River North digs. Sticking around for a while? Peruse page after page of vintage and non-vintage Champagne and sparkling bottles from France, Italy, Spain, the US and more. Pair it with tasty snacks like bubbly-battered cheese curds or a banh mi tartine, plus the option to add on a caviar bump for $10. A weekday happy hour is a solid option to ball on a budget with select $12 wine pours and bites like sliders and oysters.

601 N. State St.  (map)

Interior of The Press Room
The Press Room
The Press Room

The Press Room

West Loop

Why you’re here: You’re killing time while waiting for a table at another West Loop hot spot.

What you’re ordering: Head down the stairs and enter the candle-lit bar to enjoy 16+ wines by the glass ranging from Spanish Cava and Washington Cab, to Finger Lakes Dry Riesling and a California orange blend. Interesting cocktails like the “Birth of the Cool” with white rum, cucumber syrup, lime and black lava salt avoid the non-wine-drinker’s veto vote, while a menu of cheese, charcuterie and heartier plates like bang bang noodles will keep you noshing. The Press Room also features a great private room if you’re looking to share a bottle of wine or three from the extensive collection with your favorite oenophiles. A Tuesday-Thursday happy hour is a great deal with offerings including select $8 cocktails and $1 oysters.

1134 W. Washington Blvd.  (map)

Good Funk


Why you’re here: You need a post-work happy hour spot that’s not the usual joint.

What you’re ordering: Funky, natural wines that are unique representations from all over the globe. The emerald-studded bar plays backdrop to an experience that’s ever-changing due to the wide variety of small-production wines that rotate onto the menu. Here you might find a pet-nat from Illinois or a cab franc from the Loire Valley. You can also take an adventure through one of five “funkified” wine flights, including an option to leave your fate in the hands of the “winetender.” With the backing of Bonhomme Group, you know food is no afterthought here. The food menu is equally international with dishes ranging from roasted piquillo labneh with lavash to kampachi tiradito with salsa, avocado and charred lime.

180 N. Wacker Dr.  (map)

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Interior of Soif


Logan Square

Why you’re here: You want to forget the fact there’s a brutal Chicago winter outside at this cozy basement bar.

What you’re ordering: Head down the stairs behind Testaccio to find a sultry wine lounge with velvety decor (and equally velvety tannins on the menu). Wines by the glass are laser-focused on French producers, while bottle offerings are succinct, yet playful, from across Europe and the States. Soif’s food menu features classic wine pairings like caviar and assorted meats and cheeses, as well as modern plates like a foie gras brulee with poppy seeds and hazelnut.

2456 N. California Ave. (map)

Charcuterie board spreads
Victoria Shapow


North Center

Why you’re here: You’re meeting up with your crew for a pre-dinner drink.

What you’re ordering: A selection of apps and natural wines in this casual, neighborhood wine bar. Apero offers quite the extensive array of wines by the glass, including 10 options of orange wine alone. Wine-lovers will delight in the opportunity to mix and match pours across all colors of the wine-making rainbow, and it doesn’t hurt that Apero’s food menu is equally as colorful. Take the pesto tartine on house bread with pickled peaches and trout roe or the charcuterie board.

4160 N. Lincoln Ave.  (map)

Webster’s Wine Bar

Logan Square

Why you’re here: You have respect for one of Chicago’s original wine bars.

What you’re ordering: This Chicago classic has been pouring low intervention wines since ‘94 (read: before it was cool). There’s really something for everyone here. From small-scale production wines by the glass and bottle, to unique cocktails like the Munches ‘N Bunches with tequila, carrot, fresno, lemon and aloe, plus beer and spirit-free wines. Browsing the massive bottle list will work up an appetite. Webster’s food menu is one of the most substantial of the wine bars on this list with usual suspects like oysters and cheese, but plenty of other plates ranging from smoked trout dip to a rabbit pot pie.

2601 N. Milwaukee Ave.  (map)

Birds-eye view of oysters and wine

Rootstock Wine Bar

Humboldt Park

Why you’re here: You’re looking for a not-so-fancy date night.

What you’re ordering: Relax in Rootstock’s dimly lit lounge with a glass of wine from the interesting, yet abridged list. The Humboldt Park wine bar takes an educational and storytelling approach with its menu, informing winos of the producers and each wine’s unique flavor composition. There’s also a well-rounded global beer, cider and vinous cider (beer and wine blends) menu for those looking for something other than wine. And while you can order a variety of small plates, the larger plates on the ever-evolving food list caught our attention. A  recent menu showcased sirloin tartare with salsa verde and pecorino, an apple salad with horseradish cheddar and spiced roasted peanuts, and a beef and lamb shepards pie.

954 N. California Ave.  (map)


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