What are the best bars in Chicago?

Answers from Our Experts (13)

I really like Bernard’s, which is actually in the Waldorf Astoria. I like Untitled. It’s on Kinzie. It’s a cool little speakeasy. It’s dug out; it’s in an old basement spot. Right when you walk in there’s a massive stage in the center of it. During the dinner hours, there’s usually a great jazz band playing. It’s a cool room — a cool, dark room with good food. Love it.

I really like The Violet Hour. It’s right across from Big Star, it’s also owned by those guys. I think that’s a very unique place, really awesome. When I am down on the other end of Michigan Avenue by the Art Institute, slipping into The Gage for a drink is always fun. I think the bar at the Primehouse is also fun, and the burger’s really good there.

Sable Kitchen & Bar, The Violet Hour and The Whistler.

Chicago has a lot of new places that have opened. If you get a chance, go to The Violet Hour, which is in Bucktown, serving up the classics. Right across the street is Big Star. Big Star is a honky-tonk lounge; you see a lot of characters there. You have a lot of good music; you can eat a taco. They focus a lot on brown spirits. It’s not so much the mixologist crave, but you can get some good wine, good cocktails. If you were looking for one of those places to be impressed, you have to stop in the Aviary. Love it or hate it, it’s impressive what they do with their cocktails. With the new head bar chef there, the cocktails are really creative.

When people come in town, one of the places I bring them to is The Aviary. And that’s Grant Achatz’s new bar that’s next to Next. When it originally opened, it had Craig Schoettler, who was one of the sous chefs from Alinea, as kind of the bar chef. The Aviary completely reinvented cocktails; whether you consider them cocktails or not, they certainly push the bar as far as what’s going on in drinks. And it didn’t necessarily connect back to a cocktail experience, but they were doing things where they’d have, for instance, an old fashioned that was inside of an ice cube, which is an amazingly cool presentation experience, but they were using a really boring whiskey. Charles Joly is now the mixologist there, and I think he’s one of the best in the country. He’s taking all of that innovation from the kitchen, but he’s bringing a little bit more classic cocktails, as far as the spirits, liqueurs and bitters that he uses. I think right now it’s the perfect storm for anyone who wants to see the level of where you can go to when you have a separate whole kitchen for making cocktails, you’re average cocktail is $20 and you have a sous chef that does nothing but make three cocktails, you know? It shows what you can do with that sort of perfect environment. That’s a great spot.

Farmhouse is another one. And Farmhouse is on Chicago Avenue just off of Michigan Avenue. But you feel like you’re in a farmhouse, and it has a huge gin collection. It has every local spirit you can possibly get. It’s got all local beers and serves great fresh seasonal cocktails.

Sepia is another one. Josh Pearson is the mixologist there. It has a very seasonal cocktail list. It’s a small bar, but it’s the bar for the restaurant. I think that anytime you have a restaurant bar where you can get a great craft cocktail by one of the city’s best mixologists and then order food from Andrew Zimmerman — he used to be at Park Hyatt Chicago’s NoMI — that’s a pretty remarkable experience.

Telegraph — that’s a great spot. The Drawing Room, I like that place. Scofflaw, which is new, is right around the corner from my house, so that helps.

We used to go to The Drawing Room. It’s a subterranean cocktail lounge. Charles Joly used to run the program there. Now, Cristiana DeLucca, his protégé, took over, and it’s open pretty late. It’s across the street from our house, so we like to duck in there and get a quick cocktail. It’s a really nice, sophisticated ambiance. It doesn’t get too crazy, and the cocktails are absolutely delicious.

Probably just right next door to here, we have the Haymarket. It’s a brewery that opened around the same time as Girl & The Goat. They make awesome beers in house.

I don’t really drink spirits, so I won’t go places that just have cocktails or beer. But Rootstock, Telegraph, Au Cheval — just around the corner from us here at Perman Wine Selections — they actually stock a few good wines. I go to Au Cheval a lot. At The Purple Pig, you can always get a great glass of wine and a bite — that’s on Michigan Avenue a little bit north of The Gage.

My friend Stephen Cole runs Barrelhouse Flat. It’s a great-looking place with a casual spot downstairs and an upstairs area that feels more like an upscale parlor. And there’s a pool room with fireplace. That’s in Lincoln Park, about four to five blocks east from one of my favorite bars in town, Delilah’s. It’s a dive bar that’s been there for about 20 years — way before the neighborhood became as good as it is now. It has one of the most amazing American whiskey selections and scotch selections in the city. Owner Mike Miller is a huge enthusiast of whiskey, and it shows. He’s got stuff that you will never be able to get again. Delilah’s flies under the radar and is definitely a throwback to the late ’80s and early ’90s.

I love Maude’s Liquor Bar in the West Loop. I love being in that cool space and I love that violet cocktail they make. I also like sitting at RL [inside the Ralph Lauren store] at the bar off Michigan Avenue. It’s a very skinny bar, but I love being in that environment. And I love Ralph Lauren. His sort of lifestyle and the environment that he creates is so classic and chic and beautiful and library-esque.

It’s not like you’re going to get a great drink, but it is fun to go to Green Mill. I like that whole Chicago-Al Capone feeling at Green Mill. I think Sepia has good drinks. I don’t want to eat there but I like their drinks.

The California Clipper is this rockabilly bar on California, pretty west of downtown. It’s so fun; it’s a whole other world. Everybody dresses up and it’s a cool, old bar and that’s actually a really classic old place. It’s like old Chicago — you’re not going to get good scotch or whatever you want to drink, but it’s a fun environment and it’s got live music.

Jaydine Sayer

Sometimes it feels like there’s a bar on every corner in Chicago, and in some neighborhoods this actually rings true. Dive bars, cocktail lounges, beer meccas, dance halls, taquerias — this city has it all. Here are a few I think are worth a visit:

The Violet Hour: This cozy, candlelit spot in hip Wicker Park was one of the first to get in on the bespoke cocktail craze. Make a reservation — you’ll need it.

The Aviary: While you may head here because you couldn’t score tickets to dine at Next (chef Grant Achatz’s adjacent restaurant), The Aviary is a worthy destination on its own. Drink concoctions are made with precision and insane creativity.

The Old Town Ale House: Dive bars are aplenty in the Windy City, but this one serves as a much-needed relief from the ritzier spots in Old Town. Cheap beer and throwback tunes abound.

RM Champagne Salon: Hidden off the West Loop’s buzzy Randolph Street down a cobblestone alley, this posh lounge serves bubbly and lots of it.

Big Star: Go to this Wicker Park spot for stiff whiskey drinks, potent pitchers of margaritas, killer tacos and excellent people watching.

Lauren Viera

Opened on the heels of highly decorated chef Grant Achatz's impossible-to-get-into Next, Aviary is the cocktail lounge of the future, borrowing Achatz's penchant for molecular gastronomy, applied to cocktails. Expect to be dazzled by flavored ice, scented smoke and drinks whose flavors alter in between sips. Downstairs is a speakeasy called The Office, Aviary's delicious antithesis rooted in the classics, with prices built for the private-club set.

Chicago's original craft-cocktail lounge is The Violet Hour, located in the heart of hip Wicker Park. There is almost always a line (there is no loitering around this bar) and there are house rules (no cell phones, no light beer), but the luxurious experience of sipping a pitch-perfect classic or one of the house cocktails is well worth the fuss.

The tiniest bar in Chicago, aptly named The Matchbox, is a respite for old fashioned drinks served at high proof with low attitude. If you're lucky enough to grab a stool (there are just over a dozen), don't leave -- you may have trouble standing up when it's time to go.

Member Answers
  • Jaydine Sayer, New York, San Francisco, London
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