A Foggy Weekend in the Windy City

Jordana Nicholson explores Chicago

Nashville-native Instagram star @JordanaClaudia spent a foggy weekend staying with us and exploring Chicago. See her tips on making the most of being rained in – trust us, Shake Shack room service makes everything better.


Checking in to my stay at the Chicago Athletic Association hotel after our roadtrip up to Chicago. This boutique hotel opened in a restored Venetian Gothic building on Michigan Avenue – built in 1893, it was previously an exclusive men’s club!

To Cindy’s Rooftop we go – sippin’ a cocktail that tastes like a spring garden and enjoying this beautiful and chilly view of Millennium Park.

I’m on a mission to squeeze as much eating and exploring into my visit as possible, although there’s not much reason to leave the hotel! Feeling so rested and ready to take on the day after a good nights sleep in this glorious room.

Adventure shoes on and ready to go – but really distracted by the lobby floors! Just look at that original mosaic tile. A ton of the Loop’s major attractions, like the Art Institute, Chicago Cultural Center and Millennium Park, are within walking distance, as are trains to other pockets of the city!

A cozy spot on the second floor of the Chicago Athletic Association hotel. The Drawing Room has all the moody vibes thanks to original fireplaces and gorgeous wood carvings throughout. Taking a break from the cold and warming up right here. Already dreaming about some Shake Shack room service for lunch.

Fun fact: the hotel is the only one in the world that delivers Shake Shack straight to your room! Pinch me.

The prettiest window seat you ever did see. It’s a rainy and grey morning here in the city and we’re about to make our way down to The Drawing Room to sit in front of the fire and sip some hot tea… Do I have to check out?

Loving the intricacies of the hotel’s main entrance.

Chicago, you’re even pretty in the rain. I love that the Cloud Gate is right across the street!

Bye, Chicago! (See Chicago Athletic Association hotel’s pretty facade peeking out in the top left?)

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