This Friday Roundup is comin atchya right in time for a warm and sunny Chicago weekend! Who wouldn’t want to drink a cocktail on a rooftop on a nice night?! Or on a Sunday Funday? Am I right or am I right?! Tis the season to be outside, and these places make it fun, insta-worthy, and delicious.
Now, if you google “Best Chicago Rooftops” or “Hottest Chicago Rooftops” – you’ll find a bunch of the places I list here. But I tried to take this one a little further and cover a few different neighborhoods instead of just the River North see-and-be-seen type places. I’ve also included some options with killer menus, because let’s be real here. When you’re drinking all afternoon or all night, you might need some food, too! ? Now let’s dive in…
Best Chicago Rooftops
Want to sip a cocktail while looking over the Chicago River and/or the Tribune Building and Michigan Ave? Thanks to the rooftop bar at LondonHouse, you can! I’m actually going back next week, so stay tuned for some more footage of this gorgeous place on my Instagram!
Cindy’s might not be a typical rooftop… but their outdoor space has such an iconic view of the bean that I had to include it! Just the prettiest!
The J. Parker
I honestly can’t believe I don’t have a photo from The J. Parker on my phone, because it’s one of my personal favorites!! It’s situated right between Old Town and Lincoln Park and it has the prettiest views of downtown and Lake Michigan. Plus, you can still go if the weather isn’t cooperating because they have a retractable roof! So smart.
Bounce Sporting Club
We went to Bounce a few weekends ago for a friend’s birthday and I was so impressed! The patio itself is super cute, the view is great, and they have frosé that comes with a little rubber duck! Whaaaaat?! Summertime GOALS.
While I’m getting sad to move away from the Old Town area (and that J. Parker rooftop), I’m pretty pumped that my new place will be close to Fountainhead! This North Center/Ravenswood restaurant looks like your typical neighborhood bar, except it has a huge rooftop that’s perfect for a warm summer evening.
This Wicker Park rooftop is one of my favorites because it’s really chill. You wouldn’t even know it’s there from the street, there are big TVs that are perfect for watching sporting events, and tons of seating. Plus, isn’t Whiskey Business such a cute name for a bar?
If you like sushi, you have to add NoMi Garden to your list this summer! I actually wrote a whole post about a dinner event I attended there back in 2015 (woah), because I couldn’t get over how beautiful the rooftop is, or how delicious the food was! Such a great date night spot.
The Beach House Social
To be fair, this photo was taken back when it was called Mahalo – but it looks like The Beach House Social is hanging on to the same beachy vibes the space had before. I’m excited to go back and try out their new menu!
Cabana Club at The Robey
Wicker Park might not be near Lake Michigan, but they do have the Cabana Club at The Robey! There’s a rooftop pool, 180 degree city views, and an amazing cocktail list.
The Peninsula Hotel recently opened their chic new rooftop called Z Bar. I had to miss the opening party, but in true Peninsula fashion, everything looked impeccable. One peek at the views, cocktails, and food on their Instagram feed and you’ll want to go ASAP, too!
If you like whiskey, add Drumbar to your list. This speakeasy style Michigan Avenue rooftop has an unparalleled selection of whiskeys, scotches, bourbons and cognacs. Oh, and it’s also gorgeous. That helps, too 😉
What are your favorite rooftops in Chicago?
Did I leave any of your faves off my list? If so, tell me what they are in the comments – I’m always looking for new rooftops for summer weekends! Also, for all of you Soho House members, I know that one is amazing, but I left it off since it’s members only. I’ve also heard that Aba is amazing – have any of you been yet?