Slideshow: Chicago Drinking Guide: The Best Spots for Cocktails Right Now

Old Fashioned shots at Analogue ($5)
Old Fashioned shots at Analogue ($5)

With so much creativity going on in the cocktail world today, it's almost surprising that the 'craft cocktail in shot-form' idea hasn't made bigger waves yet. For people who don't want to shoot a cloyingly sweet Kamikaze before a night on the town, head to Analogue for their rotating classic cocktail shot. The staff at this Logan Square bar recommend taking the current Old Fashioned shot special as one would a salt/tequila/lime scenario, with a lick of Demerara sugar proceeding the quick gulp of Very Old Barton Bonded Bourbon, followed with a suck on a juicy orange wedge. The mini-cocktail bursts with flavor and sets a jovial tone for drinking to follow.

The Prelude at Celeste ($10)
The Prelude at Celeste ($10)

Some people argue that bottled cocktails take the ritual out of the craft cocktail experience, but we like that they’re easy and quick to serve, and most importantly, fun to drink. The downstairs bar at River North’s Celeste offers two rotating bottled cocktail options. Try The Prelude, a tangy, Negroni-like tequila cocktail made with Olmeca Altos Reposado, Manzanilla sherry, sweet vermouth, Aperol, and orange oil. If you go upstairs for a more elegant atmosphere, aim for the refreshing Flag Assembly, which features Control Pisco, Del Maguey Vida mezcal, housemade orgeat, lime juice, and mole bitters. It’s like a smoky Pisco Sour, without the frothy egg whites. Sound heavenly? It is.

Sgroppino at Lone Wolf ($12)
Sgroppino at Lone Wolf ($12)

Going out for brunch? Forget the cliched Mimosa. If you’re looking for something a little bubbly and brimming with bright citrus, pop into Lone Wolf for one of their Prosecco and sorbet-based Sgroppinos. Instead of using traditional lemon or grappa sorbet in the Mediterranean-style aperitif, Lone Wolf makes a variety of flavorings, like this one, which features lemon, lavender, and gin. As the sorbet melts, the flavors distribute through the drink, which slowly gets slightly sweeter and more complex. It's perfect for taking the edge off a rough weekend morning, or sipping before a heavy meal.

None More Black cocktail at Longman and Eagle ($8)
None More Black cocktail at Longman and Eagle ($8)

Logan Square's Longman and Eagle is known for an impressive whiskey selection, and when in Rome, one should partake in the local beverage of choice. The None More Black cocktail stars a dose of Heaven Hill Bonded whiskey, and when combined with bitter Cynar, tangy Aperol, botanical Fernet, Scrappy’s Chocolate Bitters, and Dark Matter Chocolate City coffee, it morphs into a well-balanced, stimulating beverage. The description on the menu calls it aromatic, bitter, and coffee-forward, and we agree. It’s just a hair shy of a real black coffee, with a well-balanced sweetness that works nicely on ice.

Painkiller No. 3 at Three Dots and a Dash
Painkiller No. 3 at Three Dots and a Dash

The oversized menu at Three Dots and a Dash features a variety of classic and modern tiki cocktails. You can’t go wrong with the perky Painkiller No. 3, one of the few drinks that has remained on the menu during a recent seasonal update. A tropical blend of Pusser's Navy Rum and Appleton 12 Year sets the stage for house-made coconut liqueur, fresh pineapple and passion fruit juices, bound together with a comforting dram of cream. It’s strong, fruity and keeps the island vibes alive at this basement tiki bar, even when it’s still 8 degrees outside.

Sky Hook cocktail at The Revel Room ($10)
Sky Hook cocktail at The Revel Room ($10)

One of the main appeals at the Revel Room is a rotating selection of cocktails on tap, which are a playful delivery concept for kegged cocktails that helps the staff swiftly dole out drinks during peak hours. But if you visit early in the evening, before the hip Wicker Park crowds descend on the space, there’s often time and opportunity to chat with one of the friendly bartenders and sip on a cocktail that requires more work than pulling a draft handle. The Sky Hook is a bold, warming Scotch drink, featuring Monkey Shoulder Blended Scotch, Amaro Meletti, Coffee Heering, honey, and a float of cream. Served up and chilled, it’s warming without being hot, with a friendly honey sweetness and dark, underlying moments of chocolate and smoke. When paired with good conversation, it’s a perfect respite from the cold.

Zed's Dead at Barrelhouse Flat ($12)
Zed's Dead at Barrelhouse Flat ($12)

The Zed's Dead at Barrelhouse Flat is so zany, we think even director Quentin Tarantino would approve the reference. The cocktail, which is served on ice, features not one but two liquors (Old Heaven Hill Bourbon Bottled in Bond and Navy Strength Gin), two Amari (Lucano and Nonino), Carpano Antica sweet vermouth, and chocolate bitters. Imagine a heap of pine and juniper, lurking underneath the wintery allure of oak and baking spices, and you have the slightly bipolar but delicious Zed’s Dead.

Dealer's Choice cocktail at Berkshire Room ($14)
Dealer's Choice cocktail at Berkshire Room ($14)

The Berkshire Room takes much of the risk out of the equation by setting up a structured system for ordering Dealer's Choice. Simply choose your preferred base spirit, flavor profile, and glassware, and watch the bartender improv. On this visit, a strong but sultry mix of Maker's 46, Amaro Abano, Zucca, grapefruit peel, and Del Maguey Vida Mezcal arrived when prompted for a smoky, wheated-whiskey drink in a coupe glass. The house drinks here are solid, but why not have fun rolling the dice and seeing what different concoctions the talented staff can conjure up on the spot?