With one hand, I grab the patio railing perched 13 floors above downtown Chicago overlooking views of Millennium Park and Lake Michigan. With the other, I slowly bring an expertly crafted vodka tonic to my lips. But in my mind, I find it hard not to think of myself as a modern-day version of Wall Street’s Gordon Gekko surveying his kingdom from above.
This is just another day at the Chicago Athletic Association, where locals and visitors alike mingle to take in the eye-popping scenery Cindy’s, a popular rooftop bar. The vibe is laid back and the panoramic view of Lake Michigan is stunning.
But in a city as crazy about architecture as Chicago, it’s certainly not the only hotel to cultivate a hip aesthetic paired with excellent cocktails and panoramic rooftop views. In fact, Chicago is blessed with a number of such properties–not to mention hipster-approved hotels with in-room guitars, podcast booths, and karaoke bars.
With Chicago’s hotel scene aimed at millennials in recent years, I set out to uncover the coolest hotels in a city with plenty of them. So book your stay at one the hotels below and immediately become one of the cool kids.