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Our stay at Chicago Athletic Association hotel | Chicago Home

Josh and I recently took a little staycation trip to Chicago. His Valentine's gift was tickets to a Blackhawks game so we decided to make a weekend out of it! We had the pleasure of staying at the Chicago Athletic Association Hotel, an 1893 historic Chicago landmark located in the heart of the city. I cannot even begin to explain how incredible our experience here was - we had the most amazing time and still can't stop talking about how much we loved it. Josh and I both agreed this was our favorite hotel experience we've ever had!

We were greeted at check in with a sweet welcome note and gifted a delicious bottle of wine from Cindy's Rooftop (their incredible rooftop bar and one of our favorite Chicago spots!) We were immediately blown away the second we walked into our room which was one of the Founder's Suites. First of all, it was huge (almost as big as our whole apartment) and the historic details of the room were so beautiful I could hardly contain my excitement. If you know me, you know how much I absolutely adore historic architecture and every detail of the building was incredible. Our room had these amazing floor to ceiling windows overlooking Millenium Park with stained glass detailing. This was definitely my favorite part of the room! There is also a gorgeous built in bookshelf filled with tons of antique books and a little reading area to cozy up in. We felt like royals in here and didn't even want to leave!

And we of course need to take a second to appreciate the stunning lobby and common-spaces of the building. This beautiful space is called the Drawing Room and is open to the public. You can also order food and beverages from the Game Room during their hours of operation.

We decided to have a nice dinner at the Cherry Circle Room and it was incredible! Josh and I both started with a glass of wine and french onion soup, and ordered a delicious steak as an entrée. I also had their chocolate cake ice cream for dessert and my mouth is watering just thinking about it again. It's definitely more of an upscale restaurant, so you'll want to dress up a bit and will likely need reservations.

Even if you don't get the chance to stay here, or if you're local, I would highly recommend visiting to at least check out any of the incredible dining options in the hotel. Here's a list of all of the restaurants in the building:

  • Cherry Circle Room (open Wednesday through Saturday 5pm-11pm and Sunday 5pm-9pm, reservations suggested but not required)

  • Cindy’s Rooftop: (open Monday - Thursday 11am-11pm, Friday 11am-12am, Saturday 10am-12am, and Sunday 10am-11pm. Details available at

  • The Game Room (open Monday - Thursday 11am-11pm, Friday & Saturday 11am-12am, and Sunday 11am-9pm)

  • The Milk Room (open Wednesday through Sunday 5pm-11pm, reservations required)

  • The Drawing Room lobby & common spaces (open daily Monday through Saturday 7am-11pm and Sunday 7am-9pm)

  • The Topgolf Swing Suite (available upon reservation, and walk-ins are also welcome pending availability)

  • Shake Shack (open 11am-9pm daily)

  • Fairgrounds Coffee & Tea (open Monday through Friday 7am-3pm, Saturday & Sunday 7am-5pm)

Remember those gorgeous windows I mentioned? Well it got even better when we woke up the next morning to the most MAGICAL little rainbow light leaks filling the room from the sunrise peaking through the stained glass. I was completely mesmerized to say the least - I still can't get over it!

We also decided to order breakfast to the room to enjoy a slow morning before checking out. Breakfast in bed? Sign me up. The food was 10/10 incredible - I ordered the strawberry pancakes and Josh had a traditional eggs, bacon and toast breakfast.

The hotel is so large and has so many things to do, it felt like it's own little community. You truly could spend the whole weekend at the hotel without ever leaving! Though if you do choose to leave, you won't have to go far to see some of Chicago's best attractions. You can step right outside to walk through Millenium Park or the Art Institute just across the street, or up the street to go shopping on Michigan Avenue. It's a perfect location to tour all Chicago has to offer.

We had the absolute best time and I would recommend the Chicago Athletic Association Hotel to anyone visiting the city! If you want to experience it for yourself, you can book directly through their site

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