The Berkshire Room (photo: Leigh Loftus)

The best Chicago bars for cocktails and conversation

By Nicole Bruce

It's not easy to find a bar in Chicago where you can carry on a conversation without shouting over loud music or TVs. Sometimes you just want a solid sit-down spot for a well-crafted cocktail and good conversation you can actually hear (and, if you're lucky, free freshly baked cookies). We’ve rounded up some of the most laid-back bars in the city for catching up with friends or lingering over drinks on a first date: Here are six of the best.

The Violet Hour
Impress your date by grabbing drinks at The Violet Hour, a nondescript speakeasy-style bar in the heart of Wicker Park. You won't find a sign or obvious door—just look for a singular light bulb and the long line in front of an ever-changing mural wall. It hides some of the most renowned pre-Prohibition style libations in the nation. The James Beard Award–winning bar program features a seasonally rotating cocktail list, including the eponymous old-fashioned, and an array of sought-after spirits. The bar got its name from two poems, both T.S. Elliot’s “The Wasteland” (1922) as well as Bernardo DeVoto’s “The Hour” (1940s). The intimate, candle lit lounge—divided into three salons with elegant drapes—is dark, hushed, and prohibits the use of cell phones (it's even outlined in the house rules).
Neighborhood: Wicker Park MAP

The Aviary
As the brainchild of James Beard Award–winning chef Grant Achatz (of Alinea, Next, and Roister fame), The Aviary is no ordinary cocktail bar. Bartenders at this ultra-swank lounge are basically mad scientists using molecular gastronomy techniques to craft science experiment-style cocktails with different smells, shapes, flavors, textures, and colors—often served up in creative vessels, like a glass ship in a bottle. The menu changes all the time, but expect to drink fantastical concoctions like the Junglebird, with layers of rum, Campari, pineapple-lime syrup, and rum "pearls" suspended in the drink. Go for just a single pricey drink or splurge for a multicourse cocktail tasting menu paired with small bites. It's a good thing you can actually hear your companions at this bar—the innovative drinks are definitely conversation starters.
Neighborhood: West Loop MAP

Loyal patrons flock to Scofflaw, a gin-focused cocktail bar in Logan Square, for its reasonably priced drinks ($8 to $12) and low-key atmosphere. Even if you're not a gin lover, you'll find enticing offerings from a menu that rotates every three months. The bartenders know their way around the classics, and are equipped with a dozen drafts and 40-plus gin varieties. (Hint: Order anything made with their handcrafted Old Tom gin). Outfitted with plenty of nooks, vintage parlor furniture, and two fireplaces (plus a patio in warm weather), the Victorian-style salon is the perfect corner bar for hanging out over quality cocktails and small bites. Stick around until midnight for free, fresh-baked chocolate chip cookies from the kitchen.
Neighborhood: Logan Square MAP

The Sixth
Cozy up at The Sixth for good conversation and inventive cocktails. The upscale, yet perfectly relaxed bar in Lincoln Square seems to spark conversation—whether it's with dear friends or complete strangers. Pull up a seat at the long bar to watch the bartender make out-of-this-world concoctions, snag a table with armchairs and couches for your group, or sit in the nook at a high table for a more intimate date night spot. No matter where you sit, you'll be content with the chat-friendly decibels and mesmerizing cocktails like the Pillow Fort with ingredients like dark rum, mezcal, spice note cumin tequila, butternut squash, Falernum, grapefruitcello, and "laughter." Pair it with a side of duck-fat frites.
Neighborhood: Lincoln Square MAP

Housed in a classic Art Deco building in the Gold Coast, the rum-centric lobby bar Sparrow—which was modeled after Havana's hotel lobby bars of the 1920s—is an easygoing yet sophisticated meet-up spot for a first date or some serious catch up time with friends. While there's no food, the old-timey space features breezy, 1930s-era rum-focused cocktails in addition to a global wine list and 10 rotating draft handles. Try the Hotel Nacional (pineapple rum, apricot liqueur, pineapple, and lime) or stop in for $5 daiquiris (aka "vacation in a glass") on Mondays, or half-off wine and draft beers during happy hour from 4 to 7 p.m. on weekdays.
Neighborhood: Streeterville MAP

The Berkshire Room
One of Chicago's most respected bars, The Berkshire Room, is located in River North's ACME Hotel. The craft cocktail lounge is a blend of Old World and modern day—there's plush seating, terrazzo flooring, barrel-stave wall panels, copper light fixtures, and whiskey lockers housing rare spirits. The glossy bar has one of the world's largest and oldest antique Bourbon collections, an off-menu "Dealer's Choice" for cocktail adventure-seekers, and a short list of original barrel-aged cocktails, including the wheated Bourbon–based Weston with "coffee essence" and pipe tobacco—the perfect libation for mingling with friends like old-school mobsters.
Neighborhood: River North MAP

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