There are cheap drinks (sloshing together well whiskey and cola), and there are great cocktails for a steal. These picks are the latter.
Old School at Fish Bar (2956 N Sheffield Ave, 773-687-8177) Served in eight-ounce jelly jars, Fish Bar’s cocktails go down fast and pack a punch. A riff on a paloma, the Old School blends Jose Cuervo with triple sec, simple syrup, grapefruit juice and a refreshing splash of Sprite, garnished with a lime wedge and served on the rocks. The acidity from the double dose of citrus complements the fishy dishes here. $5.
Gin and tonic at Bridge Bar (315 N LaSalle St, 312-822-0100) This isn’t just any gin and tonic. Mixologists at Bridge craft the classic sip with housemade tonic syrup, which boasts a more complex, bitter flavor than the sugary store-bought kind. It’s balanced out with full-bodied Plymouth gin and a squeeze of lime. Snag the drink for $3 every Tuesday in August, and look for a new special from the main cocktail list come September.
Manhattan at the Long Room (1612 W Irving Park Rd, 773-665-4500) This beer-centric bar surprises us by shaking up a solid Manhattan. Made with Old Grand-Dad whiskey, the old-world cocktail passes the ultimate test: no electric-red cherries in sight. Instead, expect a skewer of the real deal, presoaked in brandy. $5 on Saturdays.
Margarita at D’Noche (2710 N Milwaukee Ave, 773-289-4274) The airy vibe at D’Noche is pure summer, and the margarita, a mix of smooth El Charro Tequila Silver and fresh-squeezed lime, is no exception. Now, for some choices: Up or on the rocks? (Up.) Salt or no salt? (Salt.) And a seat outdoors, or by the breezy open front of the restaurant? With that one, you can’t go wrong. $5 on Wednesdays.
Sangria at AraOn (160 W Adams St, 312-781-7300) This sleek sushi bar draws the AmEx crowd, but we’ll slip in among the suits to sip the Asian sangria. A blend of red or white wine and lychee juice, it’s a sweet but not syrupy riff on the Spanish classic. $5 Monday–Friday.