A Weekend in Chicago with the Kimpton Gray

This past weekend I packed up my bags and headed to Chicago for the weekend to hangout with my blogger besties. We were graciously hosted by the cutest little boutique hotel in Chi Town – The Kimpton Gray Hotel. We spent our time eating all the Chicago favorites, being a tourist in the windy city, and of course.. taking lots of pictures 😉


We absolutely loved everything The Kimpton Gray had to offer. From the beautiful city view rooms, the gorgeous cocktail bar, and their rooftop lounge restaurant. Every part of this hotel had it’s own unique touch that made it extremely warm and welcoming. The Hotel had a beautiful marble staircase, and a cozy fireplace accompanied by a coffee and hot cocoa bar. Not to mention, the location was prime for anything we wanted to do in the city- we were never more than a 10 minute Uber ride away from all the fine things Chicago had to offer. Also, the hotel had a Starbucks inside so what more could a girl ask for?! We loved being able to walk down and grab a Chai before starting our day.




I was so excited to see my friends again, and have a weekend long slumber party catching up. As you might know I met Bailey, Hannah, and Jordan through this wonderful blogging community. I love that we get the opportunity to meet up from all over for these awesome experiences, and we always pick right back up where we left off! During our first day we enjoyed drinks and apps at The Bar at Hotel Zachary in which I couldn’t recommend enough! The lounge was so inviting, and the drinks and service were incredible! A super fun place to have a few cocktails and hangout with a view of Wrigley, and all of the fun Winterland activities going on! We even got to catch a glimpse at their first wedding which was super cool.



We also of course visited the Bean and Skydeck for the ultimate Chi experience! Skydeck was so kind and gifted us early entry before opening hours so we could get some really great pictures. There is NOTHING like getting to standing on a glass ledge, 1,353 feet in the air. The view is breathtakingly incredible! If you are headed to Chicago I would definitely recommend SkyDeck!





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If you ever get the chance to visit Chicago I also highly recommend visiting the Hampton Social! It is always a stop on my list, with the best food and rosé .. or frosé if you’re in the mood. Most people stop here for the rosé all day sign which is HIGHLY instagramable 😉 For food: I love the grilled cheese and tomato bisque soup!


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Below I listed a roundup of our favorite things we did in case you are heading to Chicago anytime soon!

Where to stay: Kimpton Gray Hotel (Perfect location!)

Where to go: Skydeck, The Bean (Millennium Park), Navy Pier, Chicago River Cruise, The Magnificent Mile (Shooooppppinnng)

Where to eat: The Hampton Social (A MUST), Vapiano’s (Super good pizza +pasta, and cool environment) RPM Italian, The Purple Pig

Where to have drinks: The Bar at Hotel Zachary  (The all Sequins Everything- SO good)

We had the best weekend in Chi Town and I wanted to say thank you again to the Kimpton Gray for hosting us and making us feel so welcome!

We can’t wait to come back soon



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Hi there! My name is Kennedy and I am a small town Michigan girl who loves fashion, food, traveling, and Tequilllaaaa! I am 22 years old, a college student, and someone looking to inspire and uplift others. Welcome!

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