Chicago Athletic Association Site Visit

The rooms have beautiful bathrooms, and some rooms even have original hardwood flooring, but all are designed in a classic masculine Chicago look. 

On the ground floor of the hotel is a rotating coffee shop and Shake Shack, which you can also order as room service. The second floor is the lobby or drawing room. Guests and locals use the space to work, dine and hang out.

The Milk Room is also on this floor. By day it is a coffeeshop, but by night it is a microbar with eight seats and a thirty-minute time slot. Make reservations well in advance for this, as seating is quite limited. The largest space on this floor is the game room. Head to the back and you will find an expansive room with games like skee-ball, foosball and pool. The tables all have checkerboards, and there is of course a bar/restaurant which is open until 2am. Additionally, this floor hosts The Cherry Room, which is the fine-dining restaurant of the hotel. 

The hotel boasts an impressive rooftop restaurant and bar called Cindy's. Reservations need to be made in advance for this as well. There is often a long line to get into Cindy's, even just for after-work cocktails. However, guests get a skip the line pass and can head straight up.

Finally, this hotel has several event spaces for whatever you are planning. One of the event spaces is an old-school basketball court. When not in use for events, anyone can play on the court. 

All in all, if you want a real feel of the culture, this is a great hotel. Since this hotel is located in the loop, there is plenty to see and do within walking distance.

This trip report is part of our ongoing series on travel to Chicago. In need of further inspiration? Check out Olivia Thomas’s guide, Exploring Chicago's West Side.