Everyone loves a good rooftop. But rooftops in the city come with some caveats - big crowds, overpriced cocktails, and often more fedoras than one place can handle. To help you find some spots in the sky actually worth hanging out on this summer, we put together the first, highly official Rooftop Power Rankings section of the Infatuation Chicago Summer Guide. It’s a scientific breakdown featuring eight of our favorite rooftops “Perfect For” different occasions. You can’t argue with science.
To check out the rest of the 2016 Chicago Summer Guide, click here.
When you first walk into Cindy’s, you’ll wonder why you don’t spend more time there. The restaurant on top of the Chicago Athletic Association Hotel is absolutely beautiful, but the views overlooking Millennium Park and Lake Michigan are even better. It’s an all-around excellent time, and ideal for any size group.
Rooftop Power Points: Awesome place to bring out-of-towners, great views of The Bean and Millennium Park, fun things to eat like a foot-tall parfait.
Penalties: Really long wait times.
There is no better place to catch views overlooking Lincoln Park and Lake Michigan than the J Parker, the rooftop bar of the Lincoln Hotel.
Rooftop Power Points: Excellent views of Lincoln Park and Lake Michigan, central Lincoln Park location.
Penalties: Always crowded when it’s nice out and limited food options.
Drumbar pegs itself as a modern day speakeasy on the rooftop of the swanky Rafaello Hotel in the Gold Coast. We don’t think Prohibition-era speakeasies ever had giant outdoor patios, but we’re into the space as much as the quality bourbon, whisky, and scotch selections.
Rooftop Power Points: Daily happy hour 8-10pm, Lake Michigan views.
Penalties: A strictly enforced dress code of “no baseball caps, sandals, baggy clothes, etc” after 8 pm, Gold Coast hotel prices outside of happy hour.
A rooftop garden in the middle of River North. Unlike many of the bars nearby, Celeste is actually a cool place to grab a cocktail and hang.
Rooftop Power Points: Secret garden vibes, great cocktails, ideal for a date situation.
Penalties: Limited views, tough to get seats, and in the middle of all the other Hubbard Street bars.
Reggies is one of the few places on the near South Side with a quality rooftop, which makes it unique for the neighborhood. It’s not only a favorite for Sox fans because of its location near U.S. Cell, but it’s also a live rock music venue inside.
Rooftop Power Points: No frills, great for before and after Sox games, and live music.
Penalties: Low-floor rooftop overlooking not-exactly-beautiful State Street and Cermak, and a location your friends might complain about.
The rooftop bar at the Virgin Hotel is predictably a scene - but a fun one.
Rooftop Power Points: Comfortable couches and chairs for lounging, and a uniquely decorated space.
Penalties: Being surrounded by people who think they are the next Richard Branson but don’t actually have a job.
Citizen is the casual neighborhood hangout with not one, but two outdoor areas - a side patio and a low rooftop bar. It’s the kind of place you can show up at wearing anything with the intention of kicking it with your crew.
Rooftop Power Points: A non-pretentious environment, reasonable price points, and lots of space for groups.
Penalties: Standard bar food.
Want restaurant and bar intel like this delivered straight to your inbox? Sign up for our newsletter here.