Chicago Rooftop Roundup

It’s the first day of summer! As our friend Molly recently discovered, Chicago is truly at its best in the months of June, July and August. I think it’s mostly because the summer is so darn fleeting that there’s this huge sense of urgency that the whole city feels to take advantage of every single second of nice weather. Frankly, I end up feeling a little bit exhausted come September, but right now it’s full-on excitement mode.

I know those of you who are not stuck smack-dab in the middle of the country probably scoff at our beaches, but I swear to you, they’re beautiful. But that’s for another post. Also for another post is the amazingness that is Chicago street fairs (chicken on a stick and a cold beer while listening to live bands? Don’t mind if I do!).

But today, I am just so ridiculously excited for rooftop season! (Hence so! Many! Exclamation! Points! Sorry!) Chicago has recently had this huge surge of these incredible roofdecks, particularly downtown… it’s like this whole new way to experience Chicago nightlife and you HAVE to act fast, because those suckers close down in September when it’ll inevitably freak snowstorm at least once.

I thought I’d share some of our faves and some new rooftops that are slated to open soon or have just opened. Enjoy!


Tried and True

Roof at Wit

In a very unscientific survey of the people around me at work, I’d call this the most famous Chicago rooftop. It has a rectractable roof, so this one is actually doable year-round, but never as good as in the summer!


Great views, comfy lounge furniture, deck umbrellas, all of my favorite things. HUGE line every night in the summer, so best to go when you do dinner here first for guaranteed entry.

Casey Morans

A great way to do Wrigley without reallyyyyyyy having to do Wrigley 🙂


Unique and perfect view of the skyline from the west. I spent my 25th birthday here and it will forever go down as the birthday to remember.


I think this might be the FIRST rooftop I ever went to here in the city! Still standing as a fun, casual place for after-work drinks.


understated décor but good drinks and music with a fun scene, right in the middle of River North. Another one with historically bad lines (and historically bad ‘tudes on the doormen), but worth checking out at least once!

Terrace at Trump

suuuper swanky, you probably need reservations unless it’s a Monday or it’s pouring, and they won’t let you step FOOT on to the roof unless there’s a table available… but a great experience and an incredible view of the river and the city.

Up & Comers

III Forks

just opened in River East at the very end of last summer and we stopped by for one quick rooftop drink and I cannot WAIT to go back this summer… I predict this one will be a big hit, though its SO hard to get to (as is everything East of Michigan Ave.)


I am ridiculously excited for this one. There are speakeasy-style bars popping up all over the place, which I am prettyyyy happy about. I love unique, craft cocktails and I’m totally convinced they’ll be even better on a rooftop.


apparently opened this winter and I haven’t heard much about it, but I suspect if the rooftop is all that it’s cracked up to be, that’ll change quickly. Its actually right on the river, so I’m really curious to see if they’ll allow boats to tie up that come in off the lake – that would instantly make this place a hit.

Perennial Virant

at the Lincoln Hotel has some seriously amazing food, and their ground-floor patio overlooking the park is pretty fabulous as is… so I’m super excited for The J. Parker to open this summer. Chicago Eater reports they’re doing a themed quarterly cocktail program and first up is Mexico – Sangria 3 ways? How will I choose?

If you live in Chicago, which one are you most excited to check out this summer? If you live elsewhere, what’s your favorite outdoor bar? I need to build my nation-wide list!

Cheers to the first day of summer!


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