About to enter its eighth year, the Whistler felt like a mainstay from day one. That’s partly because it embraces the community in a big way: You'll find the work of local artists in the window, and local DJs and bands play most nights. The ever-changing cocktail list might include the spice-filled Angostura Sour this week and a refreshing Mexican Summer—with tequila, lime and jalapeño—next. Plus, there are events of interest every night, from the LGBT-friendly Slo ’Mo party to the Relax Attack Jazz Series. It’s always a killer night at the Whistler.
Nominees: The Aviary, Billy Sunday, Sportsman's Club, Weegee's Lounge
The Sixth opened last December, serving whimsical cocktails in a modern space with a relaxed neighborhood vibe in Lincoln Square. Drinks come from the mind of Benjamin Schiller, the Fifty/50 Group’s beverage director. Standing out from the pack is the Silly Rabbit, a fancy gin drink with flavored ice cubes and mint bitters. After one sip, we’re now counting on the Sixth to stir up imaginative drinks for us for
a long time to come.
Nominees: Best Intentions, The Broken Shaker, GreenRiver, Lost Lake
Graham Heubach, General Manager at Sportsman's Club
When the rest of the bars and restaurants in Chicago close down, bartenders and chefs alike love hitting up Sportsman’s Club. That’s largely because of the high quality of hospitality and lack of pretension from the bartenders—especially from Graham Heubach. He makes this bar feel like home, no more so than on the back patio on a sunny day. It’s as welcoming as your buddy’s backyard (but with a daily rotating list of expertly crafted cocktails). Settle in and drink like the in-crowd with the Low Life (a bottle of Miller High Life and a house shot of whiskey or amaro for a mere $5). This is Graham’s place, and there’s nothing he’d like more than for you to have a great time.
Nominees: Christian Hetter—The Berkshire Room, Sable Kitchen & Bar team, The Drifter team
A formidable list of craft beers dominates this sprawling two-story spot with multiple bars. It’s an Andersonville staple, pouring local and international brews, both on draft and in bottles or cans. The bar has special tappings and charity kegs, so be on the lookout as you peruse the 60-plus drafts—if you see a rarity, be sure to snag it (we found Almanac Beer Co.’s Ginger Gose the last time we stopped in). There’s also an encyclopedic bottle list, plus eight wines on draft if, for some insane reason, you can’t find anything frothy to fit your fancy.
Nominees: Bangers & Lace, Clark Street Ale House, Map Room, Small Bar
Delilah’s—with its slasher movies, punk music and $1 beers—doesn’t seem like the kind of place where you’d find an impressive whiskey list, but beware of first impressions. The bar stocks more than 750 whiskeys from 15 countries, including bottles from more than 70 Scotch distillers and many single casks. Owner Mike Miller is a local authority on whiskey and makes sure his bartenders are well-versed. Love old-fashioneds? The staff will find the right whiskey for you.
Nominees: Billy Sunday, Masa Azul, Mezcaleria Las Flores, Scofflaw
Sprawling Gold Coast restaurant Nico Osteria has an extraordinary bar program to match its equally wonderful menu (we love the grilled arctic char with pickled ramps). While the restaurant proper predominantly serves wine for pairing, the bar attached to the main dining room, Salone Nico, serves some of Chicago’s best cocktails in fittingly lush digs. Enjoy snacks alongside a house-invented cocktail like the bright Amaro Uva, with Ramazzotti amaro and Broker’s gin, or dig into the lengthy wine list, which features an excellently curated selection of small producers and vintage Italian vinos.
Nominees: Analogue, GreenRiver, Longman & Eagle, Presidio
The Heavy Feather
Stepping into the Heavy Feather is like entering another era—the ’70s, to be exact. Overstuffed chairs, ferns and dim lights transport you but never feel kitschy. Thank the design team from Threefold for the trip back in time, with woodwork from the firm's Steven Teichelman, partnered with Scofflaw Group's Andy Gould, Mandy tandy, Kris Nagy and Danny Shapiro. As for booze, expect retro cocktails like grasshoppers and Harvey Wallbangers from Doug Phillips that are decades better than the originals.
Nominees: Milk Room, Queen Mary Tavern, The Sixth, Three Dots and a Dash