Really, when you stamp the name Trump on something, it's a least worth a look-see. The Terrace at Trump is worth that and more. You can't plant yourself more firmly in the sky than at this 16th-floor downtown oasis. If any word other than "baller" comes to mind once you're up there, please let us know. As we gazed down on almost every major landmark in Chicago we thought to ourselves; there are better views of Chicago, but they don't come with cocktails.
The Terrace at Trump, 401 North Wabash Avenue (at State Street); 312-588-8000.
Two delicious words sum this place/bar up; beer and umbrellas. We could probably stop typing right here and you'd get the point, but indulge us, hmm? Twisted Spoke is one of those divine rooftop bars that’s perfect for a daytime hangout requiring tons of sunblock and a cab ride home. With a Bloody Mary menu that will make your head spin (in more ways than one), this is the perfect spot to try for your next weekend brunch. Pray to the weather gods that we can start enjoying this one on the reg soon!
Twisted Spoke, 501 North Ogden Avenue (at Grand Avenue); 312-666-1500.
We adore Chicago (obvi), but still we like to transport ourselves to Los Angeles every now and then. That's where Zed451 comes in. Up a super-glam staircase is a rooftop oasis, the likes of which the Midwest has never seen. Everything is zen, posh, and possibly a little too welcoming. We've been known to camp out there for hours, and we're sure this summer will be no exception. Summer cocktails here are can't-miss. We suggest the California 75, but do as you like, it’s summer.
Zed451, 739 North Clark Street (at Superior Street); 312-266-6691.
In the heart of Boystown is a rooftop bar that's an instant party. You can toss some chairs and a table or two on a roof deck in Chicago, and people will flock to your banner. Sidetrack actually took the time and love to build a huge outdoor wonder club where we can sip cocktails, mingle, and bask in the Midwestern sunshine (if there is such a thing). Sidetrack; 3349 North Halsted Street (at Roscoe Street); 773-477-9189.
Market Bar is possibly the most gorgeous, posh roof chill-out you'll find in the city, but it's also got the crowd and energy of a full-on nightclub. Outdoor cabana tables and a consistently awesome DJ lineup should let you know that your weekend plans are officially made. Grab your go-to girl's night outfit and enough pals to fill a taxi, and get moving. The view of downtown Chicago is simply stunning, and for some reason looks even better with a Diablo Margarita in your hand. It's okay to email us this weekend and tell us how much you loved it. We won't mind. Market Bar, 1113 West Randolph Street (at May Street); 312-929-4787.