Sister’s Staycation in Chicago

This weekend my sister’s and I did a little staycation in the city – a first for us, but certainly an event that should be repeated yearly. Having grown up in IL, there has always been something attractive and a little magical about downtown. For a long time it was the big city where dad worked or the place you went when you were up for an adventure or ready to experience some culture. We were able to do both this past weekend, and were treated with one of the nicest weekends the city has seen in several months! What luck. conrad2

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We stayed in the new and swanky Conrad Chicago. The hotel is located at Michigan and Erie, which basically is a prime location to get anywhere in the downtown area. Our room and the entire hotel has a modern 1970’s vibe to it. And yet with the old school Mad Men feel it was also full of modern amenities including a panel that turns lights on and off, lowers curtains, etc…

conrad4 Saturday afternoon we toured the Art Institute of Chicago with a MuseumHack tour. More on that in another post this week, but suffice to say it was a fun and creative way to see the museum.


That evening the four of us went on a dinner cruise with Odyssey Chicago, which provided an amazing view of the skyline and a delicious meal. Again, this experience deserves its own post as well. So stay tuned for that.

Saturday evening, after the cruise, instead of going out on the town we played it low-key and hung out in the hotel’s restaurant, Baptiste & Bottle. It has a great little lounge area with couches and swivel chairs, perfect for sitting around and talking. IMG_5296

On Sunday, after sleeping in and attempting to make coffee in the room’s Keurig machine, which was more challenging than it should have been, we went to Church and then walked down to Cindy’s rooftop for brunch. Dining there was a first for all of us! We couldn’t have picked a better day to experience the restaurant. The sky was blue, the lakefront looked gorgeous and the wait wasn’t too long for four girls who didn’t bother with reservations. And the food… let me tell you, the food was amazing! The plates are meant to be shared, so we ordered a number of different things to try. My favorite dish was the chilaquiles, but the nutella and banana pancakes came in a close second.








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What a great weekend to spend together with the sisters! We all have such busy and different lives that it was great to get to kick back and spend time together with no big agendas or timeframe. We were able to talk, laugh, stroll the city, try new experiences, eat some great food and just be together.


Katy Rose
Filed In: Life