Hello, I’m Charles Bailey. The Kinn Guesthouse story is one about family, my family. Having resided in the Wicker Park neighborhood of Chicago for many years, my wife and I, with an increasingly active 4-year-old, began to feel the need to move out of the city in search of a better environment to raise our son. As a lifelong native, I saw the appeal of what suburban Chicago had to offer, especially since most of my family still lived there. But on a chance visit to see some friends in Milwaukee, I was drawn to its sense of community and quaint Midwestern charm. It reminded me a lot of the Chicago I grew up in.
It wasn’t long after that fateful trip to Milwaukee that I decided to move my family there. While exploring and getting acquainted with our new home, I found myself reflecting on the hospitality business. It conjured up childhood memories of watching my grandfather and father running The Drake Hotels in Chicago and Oak Brook for over 50 years. I remember thinking how luxurious it seemed, a 400-room, service-centric experience with doormen with white gloves, bell hops, room service on silver-domed platters and lobbies that could fit full-sized homes. Part of me thought I’d never be able to live the dream of owning a hotel of my own or of following in my family’s footsteps without that version of luxury.
But one day, when thinking about my next chapter in life, I had an “a-ha” moment. What if a life in hospitality wasn’t out of reach? What if I could create a new model for a hotel? I realized that luxury means something completely different today than it did so many years ago. The modern traveler is looking for more authentic experiences in their hotel stay. They don’t want a huge 400-room property, turn-down service, concierge treatment, or grandiose lobbies as much as they want the efficiency of self-check-in, contactless service, beautiful spacious rooms with modern amenities, and the freedom to experience a property on their own terms and comfort level, like they would at home. And that’s when I set out to redefine what luxury lodging could be.
It wasn’t long after this realization that we purchased a historic building in Bay View, renovated it and, ultimately, started our journey in hospitality, just like my father and grandfather. And now you know how kin led to Kinn.
We look forward to meeting you and sharing our dream with you at Kinn Guesthouse.