Favorite Chicago Rooftops

Seattle Blogger Sportsanista sharing favorite Chicago Rooftop and wearing Cotton Candy Sheer Maxi Dress in CreamChicago summer are like nothing else! You’ve waited nine months for warm weather and sunshine and when it arrives, everyone comes out from their caves ready to spend every minute outdoors. The atmosphere during a Chicago summer is like a heartbeat – it has it’s own pulse of energy that everyone wants to be a part of. Chicagoans LOVE a good patio / rooftop moment in the summertime, because why not? We just spent 9 months starring at the rain and snow hit our apartment windows! Today I’m sharing some of my favorite Chicago Rooftops, where they are located and what they to offer your summer enjoyment!

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Seattle Blogger Sportsanista wearing Cotton Candy Sheer Maxi Dress in Cream on the Hoxton Chicago rooftop
Seattle Fashion Blogger Sportsanista wearing Chicwish Cotton Candy Sheer Maxi Dress in Cream and Sam Edelman Patti Sandal


What’s better than a rooftop during the Chicago summer? A good outfit to go with it of course! This Chicwish Texture Dress is an absolute dream! The texture is super unique and fun, but sheer top of the dress gives it this super feminine and sexy feel. For this look I styled it with these Strappy Sandals, but it can easily be styled with a pair of flats or even sneakers!


  1. The Hoxton | West Loop | Great westside rooftop with cocktails, swimming pool and a South American restaurant
  2. Aba | Fulton Market | Amazing Greek Restaurant and wine list
  3. J Parker | Lincoln Parker | Great for cocktails and atmosphere – younger crowd
  4. Cindy’s | The Loop | Amazing views of Millennium Park and great brunch – somewhat touristy
  5. Drumbar | Gold Coast | Great date night cocktail place – we have our first date here
  6. Soho House Chicago | West Loop | You need a member to get you in, but it’s the IT place in Chicago

My favorite Chicago Rooftops
Fashion Blogger Sportsanista wearing Chicwish Cotton Candy Sheer Maxi Dress in Cream and Nude Sandals on Chicago Rooftop

Photography by Iron and Honey

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Chicwish Texture Dress | Sunglasses | Strappy Sandals


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