Where to Bar Down: Logan Square

A neighborhood is only as good as its supply. So whether you’re tracking down the hippest happy hour or a venue for thirst relief, choose these 5 Logan Square watering holes.

1. The Whistler

chicagotribVoted Bar of the Year by Time Out Chicago, the intimate cocktail room/entertainment space has much to offer. Basically, miscellany is the name of the bar’s game. From live music and art installations to theme nights (once transformed into Star Wars cantina) and daily drink amendments, The Whistler checks monotony at the door. One of those “you had to be there” places…every night. Try some of their newest refreshments like Divorce Papers (rum, bitter, pineapple, coconut, lime) before they switch.

Hours: Monday through Thursday 6PM–2AM; Friday and Sunday 5PM–2AM; Saturday 5PM–3AM, 2421 N Milwaukee Ave. 

Photo: Chicago Tribune

2. Billy Sunday

billysundayThis crafty nook stocked with expertly mixed drinks and punchy names will make a Sunday or any day memorable. Flaunt your Box Lunch (goat’s milk, genepì, Palo Cortado,
oatmeal spices), or spill dark secrets over a Blackthorn (14-year pot-stilled Irish whiskey, Sloe gin, vermouth di Torino,
Willett Bergamot bitters). Billy Sunday also hosts snacks and jars (potted salmon, chicken liver mousse) to accompany your sips. Let the bar stewards accommodate your fancies, or sign up for cocktail making classes with the masters.

Hours: Monday through Friday 5PM–2AM; Saturday 3PM–3AM; Sunday 3PM-2AM, 3143 W Logan Blvd. 

3. The Heavy Feather

HeavyFeather+(31+of+50)Ease into a dim, amber glow and curious mix of decor cast upon this 70s burrow. Nestled above The Slippery Slope (will handle the after party), The Heavy Feather invites cocktail cravers and nostalgia seekers to stay a while. Approach the bar for a Tony Negroni, Shark Attack (three rums and four fruit representatives), and other features, or hide out in cushy booths with the classics. You won’t find rations here, but the tonic space and diverse liquid options should be satisfying enough.

Hours: Nightly 7PM, 2357 N Milwaukee Ave. 

4. Analogue


Food reigns equal, if not supreme here. Focus in on “cocktails and cajun” at AnalogueDigest a menu of locally farmed, Southern-inspired comfort (collard greens, catfish deville, shrimp po boy, file gumbo and basket of biscuits). Clever cocktails, fishbowls, beer and other options will frame your eats nicely. The kitchen closes around 11PM, clearing space for DJs and dancing.

Hours: Nightly 5PM except Mondays; Saturday and Sunday for brunch 11PM-3PM, 2357 N Milwaukee Ave. 

5. Scofflaw

scofflawFor all the gin genies out there, your wish has been granted. Experience Scofflaw’s seasonal cocktails, everlasting gin list and nourishment. Sandwiches brim with beef patties and Russian dressing (Mickey’s Famous), and pork belly, applesauce, and crispy shallots (Belly). Fries mingle with pimento aioli. Complementary and freshly baked chocolate chip cookies appear at midnight. The magic is real. Settle into this atmospheric and cozy corner draw with fireplaces, couches, ruffled curtains and disparate chairs. The interior speaks to ornate, European design with a rustic touch, while outside hosts good, Logan Square vibrations and a modest seating strip.

Hours: Monday through Friday 5PM–2AM; Saturday 11AM–3AM; Sunday 11AM-2AM; Kitchen open till 1AM daily, 2AM Saturday, 3201 W Armitage Ave. 


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