Stockyard Pony at Big Star, $7: The perfect segue between summer and fall sipping: Aperol (an aperitif with sweet orange tones) and lemon juice provide a nice balance to the smoky and spicy J.W. Dant bourbon and Angostura bitters. If you’re lucky, Hank Wiliams will loop overhead on an old 45, providing the perfect soundtrack to leisurely bourbon sipping. But pace yourself, or you too will be singing the Honkey Tonk Blues.
Big Star: 1531 N. Damen Avenue, Chicago, IL 60622 (map); 773-235-4039; bigstarchicago.com. Cash Only.
Admiral Schley at The Whistler ($8): Mixing bourbon with rum? Before you scream, “ blasphemy!” we suggest sampling the Admiral Schley at The Whistler, a tiny bar on the city’s northwest side in Logan Square. The gently sweet Old Weller Antique bourbon combined with Gosling’s Black Seal Rum makes for a spicy base with notes of vanilla, honey and butterscotch. Lemon juice and demerara syrup tone down the alcohol just enough to make this cocktail easy to sip, yet still boozy.
The Whistler: 421 N. Milwaukee Avenue, Chicago, IL 60647 (map); 773-227-3530; whistlerchicago.com
Julep de Chambly at Longman & Eagle ($8): This Logan Square whiskey bar and eatery puts a citrusy twist on the classic mint julep. All of the traditional ingredients are present (mint, sugar, and, in this case, Old Taylor Bourbon), but the addition of lemon juice adds a welcome acidic element to this otherwise sweet drink. The inclusion of Ephemere, an apple-flavored Canadian white ale, makes for a touch of Granny Smith fizz.
Longman & Eagle: 2657 N. Kedzie Avenue, Chicago, Illinois 60647 (map); 773-276-7110; longmanandeagle.com
A Bubbly Creek at Maria’s Packaged Goods + Community Bar ($8): This Bridgeport dive pays tribute to the Union Stockyards with a concoction inspired by its grimy drainage canals. (Hence the brownish-green color.) The 100-proof bonded Old Grand Dad bourbon comes through strong, making this a drink for slow sipping. A blood orange bitters rinse and Gosling’s Ginger Beer add a balancing tartness.
Maria's Packaged Goods + Community Bar: 960 W. 31st Street, Chicago, IL 60608 (map); 773-890-0588; community-bar.com
Tennessee Squeeze at The Southern ($9): Sweet as a southern belle, this cocktail is perfect for those who prefer their bourbon pared down. Bulleit Bourbon and peach bitters pack a lot of floral and herbal spice notes, while a combination of orange juice, lemon juice, and honey acts as the proverbial ‘spoon full of sugar’ to help the alcohol go down. It’s cocktail that’s tangy on the first sip with a buttery finish.
The Southern: 1840 West North Avenue, Chicago, IL 60622 (map); 773-342-1840; thesouthernchicago.com