WHY HERE: You don't have to stay at the Freehand in order to enjoy drinks from one of the best bars in town. Stay classic with the Grandma's Old Fashioned, which has an apple cordial component; or try the Return of the Mack, a drink made with spiced rum and roasted butternut squash. It's a little whimsy mixed with a whole lot of skill.
WHY NOW: Drinking in hotel bars is an age-old tradition that involves people watching, stiff cocktails and maybe a stranger or two. Plus, at this Windy City hot spot, you can score some stylized street food bites while you imbibe.