Olio 8: Our Favorite Bars in Chicago

Hopleaf Bar

Inspired by the beer and food culture of Belgium, Hopleaf is a mecca for fans of craft beer. This relaxed, convivial Andersonville neighborhood pub caters to beer snobs with its ever-changing menu of 68 draft selections and bottles. Not beer drinker? The bar also offers a selection of fine wines, spirits and cocktails, cider, and meads that pair well with the seasonal menu of creative Belgian-focused eats. Try the duck reuben with truffle fries, or the famous mussels & frites.

THE VIBE

This venue is for those 21 and up, but the patrons are usually much older. Lacking screened distractions, games, or live entertainment, Hopleaf is for drinking, eating, and actually being able to have a conversation with your friends.

Photo courtesy of Hopleaf Bar

Lost Lake

Even when it’s cold out, the ambiance is always warm and buzzing inside this little island paradise. This slightly cheaper, slightly less crowded, more Logan-Squarey version of 3 Dots and a Dash (also worth a visit) serves up creative, tropical cocktails, like avocado daiquiris, and giant, shareable drinks with Insta-worthy garnishes. The Hawaiian-inspired menu isn’t anything to write home about, but will help if you’ve had too many sugary rum drinks.

THE VIBE

Self-described as a “stylish tropical oasis-meets-flotsam strewn island hut,” Lost Lake has something to look at everywhere you turn. The tiki bar’s banana leaf-print wallpaper is cute AF, and even the staff is dressed like its island time.

Photo courtesy of Lost Lake

Maria’s Packaged Goods & Community Bar

Eclectic, artsy, and hipster, this community based social bar and bottle shop is a hidden gem in Bridgeport, operating as a “classic slashie”--half liquor store, half neighborhood tavern. From the outside, it looks like a divey hole-in-the-wall. Enter through the tiny liquor store or the restuarant, Kimski. Then head back through the older bar and round the corner to a cool, open industrial space. The artisanal and craft beer offerings change weekly, with hundreds of craft beers in bottles, cans and on tap. The bar also features traditional and remixed classic cocktails, as well as many local and regionally distilled and brewed liquors, spirits, and beverages. When you get hungry, order some Korean Polish Street food from Kimski and have it brought to you in the bar, beer hall, or patio area.

THE VIBE

Low key, laid back, and chill like a dive, yet modern, beautiful, and spacious. Rent a board game from their collection and enjoy some great music.

Photo courtesy of Maria’s Packaged Goods & Community Bar

Scofflaw

Logan Square’s gin-focused cocktail bar offers beautifully crafted cocktails, craft beer, and small plates. Enjoy dinner and cocktails in the Victorian-style salon, saddle up to the bar, have lovely brunch on the patio, or be there a midnight to take a seat on the couch by the fireplace and treat yourself to some freshly baked cookies! Don’t skip on the old fashioneds made with their special bitters mix. And definitely try the fries!

THE VIBE

Dim lighting makes for an incredibly cozy atmosphere that is chill yet classy. This quiet little corner bar is a great place for a date.

Photo courtesy of Scofflaw

Sportsman's Club

Tucked away away from the crowds of Wicker Park, Sportsman’s Club offers classic, simple, and balanced spirit-forward cocktails. The cocktail list is limited to four drinks, which change daily, but the Sportsman's Cocktail is usually an aromatic bitter drink. The neighborhood tavern also offers a selection of craft beer (bottles or on draft from eight taps) and “terroir-driven” wine, made with unfamiliar grapes from familiar regions or familiar grapes from unfamiliar regions. There’s also a carry-out booze program, so if you like what you had at the bar, you can take some home. Instead of a Jagerator, there’s an amaro machine. They don’t serve any food, but the tamale guy is very popular, or you can order delivery, or grab a bottle of wine to take to dinner elsewhere.

THE VIBE

Hipster in all the right ways, Sportsman’s Club strives to be an “every person bar”. The decor has the feel of a French hunting club, with lots of lots of taxidermy and a tapestry of a French hunting scene. The atmosphere is dark yet warm, with no TVs in sight. This is a place to gather with friends, have a strong drink, and listen to good music. There’s also a patio out back, which is nice during the warmer months.

Photo courtesy of Sportsman's Club

The Green Mill

This old school Chicago jazz bar was one of Al Capone's favorites spots. Located in Uptown, right off of the Lawrence CTA red line stop this local gem has tons of character steeped in Chicago history. Swinging sounds are on tap nightly, from big-name artists to local late-night jam sessions. We do have to warn you it is CASH ONLY, so hit up the ATM on your way and arrive early if you want a good seat.

THE VIBE

Green Mill is fun, intimate, and lively. The atmosphere is sophisticated, yet informal, with the perfect mix of down-to-earth friendliness and class. The cozy, dimly lit romantic bar is steeped in the heady sights and sounds of the early '30s and '40s, with art deco/art nouveau décor.

The Violet Hour

This James Beard Award-winning Chicago lounge serves artisanal cocktails rooted in pre-prohibition style libations in the heart of Wicker Park. The seasonally rotating cocktail list also has an extensive selection of approachable and sought-after spirits, but no beer or wine. Check out the House Rules before you go--there’s no cell phones use in the lounge. The menu consists of elevated bar food and includes a miniature ice cream cone flight for dessert. Happy Hour is “l'heure verte,” or “the green hour” which means absinthe cocktails, baby! They also make and sell their own old fashioned mix.

THE VIBE

A single light bulb and ever-changing mural designate The Violet Hour’s entrance. The marble bar, cornflower-blue walls, high-backed blue leather chairs, velvet curtains, dim lighting, and crystal chandeliers make the place feel really elegant.

Photo courtesy of The Violet Hour

The Whistler

The Whistler stands out among the many cocktail bar choices in Logan Square because of its great music and fairly priced, yet delicious, craft cocktails. This tiny hipster hang is hard to find unless there’s a line outside. The nondescript entryway has no signage, so look for the ever-changing art out front. There’s live music or DJs playing a variety of funk, disco, soul, ‘90s, and hip hop every night. Check the site for proper recon.

THE VIBE

The Whistler is Violet Hour-esque, minus the weird cell phone rules. The dimly lit, private/intimate (read: small AF) spot is is a great place to take a date. Plus, there’s a cute little patio out back!

Photo courtesy of The Whistler