Thomas Murray, founder and artistic director of Waltzing Mechanics, enjoys the view from:
Cityscape Bar There are myriad rooftop bars and clubs around the Loop surrounding the spectacle that is our city's skyline. Unfortunately, I've found the added altitude also generally inflates the price of drinks; a glorious glass of vino above it all quickly tastes sour once the check comes. That's why when cocktails beckon me and my troupe skyward, I head over to Cityscape Bar on the 15th floor of the Holiday Inn-Mart Plaza. The inspiring vista above the Chicago River's Wolf Point pairs stunningly with their weekly "Sparkling Tuesday" event when $4 glasses of sparkling wine are on the menu. No lie, Waltzing Mechanics' entire mission was hatched perched in front of Cityscape's windows. Savvy urban explorers may also find the lengthy but entirely indoor hike from the Merchandise Mart CTA station to be a bonus when the city is in the midst of winter's frosty grip.