Last Updated On: April 26, 2018

I’m so excited that the warmer weather is finally here! If you are visiting Chicago or you live in Chicago you know that summers are really important and everyone wants to make the most of the warm weather. I love to be outside as much as a can and I each summer I make a summer bucket list of everything I what to see and do. The city is always buzzing and there’s always something going on. For the last few years rooftop bars have been really popular in the city and every year there are a few new rooftops that everyone wants to try (see my list below for all the newest rooftop bars). If you love seeing stunning city views or the beautiful lights at night, then there’s really nothing better than having a cocktail or two on a rooftop.

I have a few favorite rooftops in Chicago for all very different reasons. Cindy’s at the Chicago Athletic Association Hotel has probably one of the most stunning rooftop views in the entire city. You can see the Lake, Millennium Park, as well as a beautiful city view. The cocktails are really good and they have a great but a little pricey brunch on the weekends as well.

I also love Shanghai Terrace at the Peninsula Hotel. It’s like a little secret garden above busy Michigan Ave. And it’s the Peninsula so you know that everything there is really amazing.

Another favorite rooftop to go to is Streeterville Social at the Loews Hotel. Every time I have been to this rooftop it’s a little less crowded than the others and I also really like that it’s more of a large garden above the city. The view is very pretty and you can feel free to spread out on the lawn or lounge in a cozy chair.

For the first time last year, I went to the Gwen Hotel because my girlfriend and I had been really wanting to try the prosecco popsicles. They were really delicious and I highly recommend them! Definitely worth the $$$ because you only need one. After a day of shopping downtown, this would be perfect afternoon spot to go to.

You might also like A Girl’s Guide to Happy Hour in Chicago

prosecco popsicles at the Gwen Chicago

prosecco popsicles at the Gwen Chicago

You also might like: Afternoon Cocktails at Noyane

Download and save my Girl’s Guide checklist with the best places to grab a rooftop drink in Chicago.

Download my guide so you can plan a perfect girl’s night out having cocktails at some of the best rooftops in Chicago. You can even plan a night to do a rooftop crawl. My suggestion would be to head to Cindy’s as early as you can for happy hour before all the crowds and to enjoy the view before the sun goes down. Then I would head to either Shanghai Terrace or one of Chicago newest rooftops Noyane, and then maybe end the night at Drumbar or Celeste.

Free Download: Save a copy of this checklist I made:
A Girl’s Guide to the Best Places to Grab a Rooftop Drink in Chicago.

Best Rooftops in Chicago


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A Girl's Guide to Chicago

Based on the true story of a girl in her twenties who packs her bags and follows her lifelong dream of moving to Chicago. Take a journey with Kelly and discover the hidden gems you never knew about – as she starts a new career, makes new friendships, and even falls into an unexpected romance. Learn more...

  • • Perfect for the girl who loves exploring and living in Chicago.
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Girl's Guide Chicago