I’ve said it before and I’ll continue to say it, rooftop season is my FAVORITE season in Chicago. Now, don’t get me wrong, I love Chi all year long, but, rooftop season – you just can’t beat it! (Maybe it’s because I’m from the midwest so rooftop season is a big deal to me, mainly because I can’t drink a cocktail on a rooftop or outside during the winter without freezing or being in a trendy igloo? I don’t know, probably.)

Anyway, I’m constantly asked what my favorite bars in Chicago are and aside from Three Dots and a Dash, the majority of my favorites are rooftop locations. If you didn’t know, River North is the neighborhood I visit most often so that’s where a lot of these rooftop locations are (or close to)!

London House Rooftop

You guys! If you want one of the BEST views of the river, LH Rooftop is the place to be! Such a cute spot to mix and mingle while admiring the beauty of the city. Even if you’re only stopping by for one drink, it’s totally worth it.

IO Godfrey

Small bites, indoor/outdoor seating, and cute decor. I’m a huge fan of the sea salt truffle fries here paired with a chilled glass of Prosecco!

Drumbar

Looking for trendy Instagram pics? Drumbar is the place, during the day, for my aesthetic. Stop by for a happy hour cocktail, a few Instagram pictures, and the chance to really soak up the sun. I highly recommend visiting during the day!

Cindy’s

It’s ALL about the views here. The drinks are good but the views are AMAZING. You’re overlooking Millennium park, you can see Lake Michigan, and bits of the city. My literal dream. Grab a cocktail, grab brunch, but ultimately make sure you take in the views!

Roof at TheWit

Looking for a place to take your bumble date on a first date? Look no further! This fabulously swanky, trendy rooftop is the place to be in the summer. Music will be bumpin’, cocktails will be crafted, and you’ll have the ability to overlook some of the coolest cities views in the loop!

Devereaux

If you’re looking for a spot for poolside cocktails, intimate ambiance, and some of the best tasting small plates – look no further! This chill rooftop located at the Viceroy hotel is one of my favorite places to really vibe out in the summer because it mixes the typical cocktail lounge feel with a splash of fun by adding the poolside as an option.

Apogee

The cocktails here are NUTS, like actually so cool! I’m all about experiences and Apogee delivers that for me. Highly recommend date night here!

Raised

I did an entire dedicated blog post about Raised so I’ll link that blog post here. It’s still one of my favorites and the truffle fries are still SO good!

Cerise Rooftop

I’m really into feeling like I’m in my own slice of paradise and Cerise is 100% a little slice of city paradise for me. It’s super hip, really inviting, and will make you want to stay until the wee hours of the morning just soaking in the city vibes.

52Eighty Rooftop Lounge

Located on the 52nd floor of the Cambria, this gold accented indoor/outdoor lounge holds a key to my heart! The ambiance is perfect for a casual night out in the city.

 

I’m always adding to my list of favorite places in Chicago so feel free to ask for updates or more locations! Happy sipping!

 

xx, Kaitlyn