Our Fair City: Chicago Athletic Association

Whenever we have visitors, we love to take them to Chicago Athletic Association. It's name is true to it's history. It used to be an athletics club, which was recently renovated and it's classic architectural details were restored. The famous serial killer and con-artist, HH Holmes, was a member during his time here in Chicago circa 1893 - when the World's Fair was here.

It's now a space like no other, and it's a hotel so you can stay there during your visit if you wish! There used to be a pool, as well as a basketball court that you can have events in. There are wood panels were re-purposed from the old fencing club that line the interior of the elevators. The different restaurants and bars within the Chicago Athletic Association are what really make the place unique.

  • Starting from the top, Cindy's Rooftop is the perfect place for a warm afternoon. The terrace overlooks The Bean, Millenium Park, Lake Michigan and more. It's a stunning place to show guests! You can see some photos from our last visit on this post.
  • The hotel lobby reminds me of the libraries in books like Harry Potter and at ivy league schools. We love to sit in the plush chairs by the fireplaces and order some wine and a cheese plate. Also - their burger is very good! 
  • For a special occasion, I would definitely recommend the Cherry Circle Room. I have not personally dined here for dinner, but I have had dessert and port. It was the most beautifully crafted plate of dessert! 
  • For a fun night out with friends, I love the Game Room. There is the largest indoor bocce court that I have ever seen, and there are tons of shuffleboard games to play! I did not know that I love shuffleboard until celebrating a friend's birthday here. The best is that the games are free, you just need to reserve a space for your group!
  • There is a super tiny (8 seats!) bar called Milk Room, which boasts a cocktail menu featuring rare ingredients. We have toyed with making a reservation (months in advanced) for a special occasion. 
  • Where the pool used to be is now a space for pop-up bars/lounges! The recent pop-up was called the Cherry Circle Yacht Club, which was perfect because it aired America’s Cupsailing competition that was taking place on Lake Michigan! I learned that the athletics club use to have a boat, and it was named The Cherry Circle.
  • Lastly, there is Shake Shack on the ground level! It has outdoor seating on Michigan Avenue, which is perfect to grab a burger after exploring downtown, or to take a frozen custard to-go for a stroll. 

Lately, I've been thinking about friendships. I'm lucky to have a best friend, and many dear friends. I find these friends truly inspiring, I can talk to them about anything, and they are always there for me when I need an ear. I like to think that I give them the same respect. I aspire to drop everything if there is ever a moment that they need someone to be there for them, like they always are for me. However, I've had these friendships for years. As I grow older, I find it increasingly harder to create new friendships like these. I'm coming up on one year of living in Chicago, and not having a "best friend" locally has been weighing on me more. I miss having a friend that I could go out with for a glass of wine after dinner, or to go to brunch with, or to even just cuddle up on couch together, binge-watching our favorite TV shows. I know that building relationships like that takes time, so I'm just trying to be patient while looking for the Iliana to my Abbi, or the Samantha to my Carrie. In the meantime, I've been cherishing the memories that I've had with my dear friends, and my heart is open to new ones.


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