Longman & Eagle is well-known for its stellar food menu, but the bar out back (OSB) serves up a great, simple lineup of cocktails. The old-fashioned is no exception. Made with Buffalo Trace bourbon, three types of bitters, demerara and topped off with a touch of orange and lemon oil, it’s a delightful way to consume whiskey. —Clayton Guse
Sometimes, you don't want to think too hard about your cocktail. You just want to pull up a seat at the bar, order some bar snacks and have a solid, well-balanced and well-mixed drink. Cue the old-fashioned—a great classic cocktail that highlights the bite of whiskey (like its other classic cocktail friend, the Manhattan) with a perfect hint of sweetness and citrus. You can find them most places, but we dug up some of the best in the city.
RECOMMENDED: Our guide to cocktails in Chicago