The standard rooftop bar gets a poolside upgrade at Cabana Club (2018 W. North Ave.), The Robey’s sixth-floor rooftop hideaway with a distinctly beachy feel. Lounge on nautically striped couches with a cocktail and take in dreamy, panoramic views of the skyline, or face the opposite way and watch Blue Line rumble in and out from far below. Either way, it’s a sweet respite from the city grind. And yes, there’s actually a pool—though it's more of a place to dip your feet than actually get swimming done.

Below, watch food and beverage manager Matt Alessi walk through drink highlights and why “hipster paradise” Wicker Park is the perfect place for a rooftop spot. 

This video is a part of Chicago magazine's Cheers to Sunshine series, highlighting our favorite rooftop bars this summer. See more and subscribe to our YouTube channel.