We Chicagoans love summer.

I know, everyone loves summer. But we especially do. Thanks to the annual ice age that hits Chicago and lasts for what seems like a year, we need to make up for lost outdoor time and replenish our depleted Vitamin D levels more than most.

And if there’s one thing this fleeting spoil of summer has taught us how to do, it’s rooftop bars. After all, if you’re going to load up on the rays, why not be closer to the sun while you do it?

But there are plenty of activities to do in the world’s greatest summer city besides sampling its entire arsenal of roof establishments.

So, to make the summer bucket list easier for you, we put together our lineup of 10 Chicago rooftop bars that are the “absolute musts.” In other words, the rooftops that you should hit up for at least one beer sometime this summer. Or for one Pepsi.

Whatever you like to drink on the weekends, here’s where to spend your limited rooftop hours.


Despite what you might have heard, this is not a hipster place.

It just has an extensive selection of craft brews, foodie-worthy artisanal dishes, and decor of ‘handcrafted mahogany woodwork’ around a fireplace that I imagine has a mantle lined with many leather-bound books.

Alright fine, it’s the most hipster a non-underground place can get. But you don’t have to be a hipster to love good beer, and Fountainhead’s beer menu knows what it’s doing.

They even have classes for whiskey enthusiasts, which is pretty damn cool if you like whiskey more than I do.


Don’t be scared because this place is in the generally steep area that is River North. Citizen has the vibe of a college rooftop bar that was plopped right into the nether regions of rich people central. Perfect place for an affordable after-work happy hour.

The rooftop is quite literally the whole roof of the building, with plenty of space for sitting and plenty of TV’s. A few blocks east of the river, Citizen’s rooftop basically overlooks the whole block of Erie between Sedgwick and Orleans.

In the summer, palm tree-ish plants on the deck and fish/shrimp tacos on the menu give off a nice California vibe. Solid strategy.


You’ve probably gazed longingly at this place through the Brown line window, wishing you were there instead of a train car that smells like pee.

Plymouth is the quintessential hybrid of Chicago rooftop bars – up at a height that gives you a decent view, always has a great energy to it, and as far as prices go, it’s a relatively good deal.

Plus it’s open all year around, so you can cope with the summer feels when it gets cold and we all want to hide from the world again.

Parlor Pizza Bar

I had a hard time writing this one because I couldn’t stop staring at the website’s food pictures. Seriously, rooftop or no rooftop Parlor Pizza Bar has stolen the cheese-clogged arteries of my heart.

To get back on topic, yes, the Parlor does have a rooftop. According to general height standards it’s more of a raised patio, but we don’t discriminate against any kind of roof here at THESIXTHIRTY.com.

There isn’t a breathtaking cityscape view, but there is a lot of great beer, exposed brick, and pizza. If those aren’t enough, then I don’t know how to help you find happiness.


This cocktail-focused bar is atop the Raffaello Hotel in the lavish Gold Coast area, right off of Michigan Avenue.

With views of the lake and the John Hancock, Drumbar is definitely a solid place to take a sweet Instagram. But, with all house cocktails starting at $13, it’s not exactly a ‘casual weekend’ place. This rooftop is more of a “Treat Yo Self” evening a la Parks and Recreation.

Vertigo Sky Lounge

When you picture an outdoor rooftop club, the Vertigo Sky Lounge is pretty much exactly what you have in mind.

A 26 story high rooftop (on the Dana Hotel) with a killer view of the city that you can get selfies in front of, Vertigo is rather aptly named. There are countless places to sit and relax, a fire pit, and skyscrapers everywhere you look.

While it’s a little on the expensive side (naturally), the prices of their after work specials are crazy low. Like $2 sliders low. Can’t say no to that.

Twisted Spoke

You would think a biker bar would be known for its mean old fashioned, but no. The draw of the Twisted Spoke is its amazing Bloody Marys.

Oh, and the porn.

Yeah, that’s the kicker here. On Saturdays from midnight to 2:30 AM, they announce that it’s “smut time,” let you order whatever you want from the brunch menu, and play a porn flick from between the 70’s and modern day.

Twisted Spoke looks and feels like a biker dive bar, but instead of only serving PBR and other cheap beer, they have micro brews on tap and reasonably priced food.

That being said, I’ll leave you with my new favorite Yelp review quote of all time: “Enjoy your beer, and enjoy the porn.”

The Garage Bar And Sandwiches

As evidenced by their name and a website that looks like they gave up on technology, the Garage Bar is definitely more of a dive. There’s also a surprising amount of old people games, like shuffleboard and Nintendo Wii.

Whatever your age, everyone will appreciate the prices. Wednesday they have $2 craft drafts, Thursday is $2.50 Coronas/$4.50 margaritas, and Friday is $3 Founders draft day.

J. Parker

The J. Parker – Hotel Lincoln’s swanky 13th-floor rooftop – isn’t hiding from its label as an outdoor joint, with 140 outdoor seats and just 55 inside. The roof definitely makes for a relaxing scene, mixed with a high-end cocktail vibe.

This is a layup when you have something to celebrate or want to indulge for drinks on pay day.

Joe’s on Weed

The most self-explanatory one for last.

This massive property has its whole rooftop to itself, and was the ideal place to be during the Kentucky Derby. On Derby day, the Joe’s deck provides a perfect view of the ongoing madness on Weed Street below.

If you want beer, a rooftop, and live country music you could do much worse than Joe’s on Weed in summertime Chicago.

Now go get yourself some rays this weekend.

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