ROOFTOPS IN CHICAGO | WHERE, WHEN, & HOW

Rooftops have been a hot summer Chicago staple for a while. The trend is continuing to rise and it’s making finding a good one hard! I have a few tips for anyone looking for themselves or for their out-of-town friend that is set on taking in the view with a pricey drink in hand.

But first, a DON’T

Everyone and their mom think the best views they will find are at the Skylounge.

More like airport lounge. With overpriced and generic drinks, it displays a view that pales in comparison to other rooftops, you’re better off waiting in the forever line at London House.

Come prepared to wait!

Next up, just across from Millennium Park, is Cindy’s. It’s heartwarming story and charming view (and menu) promise an evening of possibilities. Take note, their mocktails are better than their cocktails. Maybe just take a peak at the view here. Or sip on their charcoal mocktail because I could live off of them.

Show up early and set a reservation.

The Up Room, located on the top floor of the Robey Hotel in Wicker Park, can have quite the waitlist on weekends. I snuck in solo. However, when my friends and I came we had to wait a little longer for some open space in the very elusive yet chic rooftop. Make a reservation early, eat at their restaurant while you wait, and enjoy a drink when you get upstairs. Or just soak in the view. It is certainly the best after-dark view of the wide city skyline.

Follow a local (& call ahead):

Many locals have struck gold with the rooftop bar, Raised. It’s not in the clouds but it is among some amazing architecture. My advice: go just before sunset. Seeing golden hour in between all the buildings is breathtaking and they’ve been highly recommended to serve a good Ol’ Fashioned.

If you’re going to a rooftop midweek, call ahead to make sure they’re not closing the roof for a private party. Happens more often than you’d think!

Need a rooftop hideaway?

Restoration Hardware’s rooftop is my favorite place to bring a book, sip a latte, or just sit and contemplate life. Or bring some pals and tuck yourself into a plush patio set while you sip on a glass of wine, the sunset views are pretty gold here, too.

CHEERS from C H I C A G O,