You’ll find it, come Sunday, on the sixth floor of The Robey Hotel.
Don’t be turned off by the lack of cabanas, though. Or the fact that, at least in the beginning, only hotel guests can swim in its pool. You can still go up there and drink margaritas next to a wood-burning fireplace surrounded by Mid-Century Modern furniture.
And back to the point, there’s a pool on a roof. In Wicker Park. Which looks like this.
What you have here is a little taste of Mexico meets Chicago. Also, octopus tostadas topped with celery root puree and steak skewers slathered in chimichuri. Not to mention some essential tamarind frozen margaritas and less essential, but certainly appreciated, 180-degree sunset views.