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Meet Ray Reiss of Ray’s Bucktown Bed and Breakfast of Chicago

Today we’d like to introduce you to Ray Reiss.

So, before we jump into specific questions about the business, why don’t you give us some details about you and your story.
I opened Ray’s Bucktown Bed & Breakfast 12 years ago, converting my photography studio/home into a 4 room bed & breakfast/home. Business was good from the start so when I had an opportunity to buy the building next door a few years ago, I expanded into the current 11 room bed & breakfast I run today.

All small businesses should reflect the owner’s personality. What better way to share my passion for good service, my obsession with collections and my love of food than running a neighborhood B&B! Ray’s Bucktown Bed & Breakfast is filled with thousands of unique “objects d’art” or as one of my former workers once quipped: Ray, you are a great curator of crap!

My lifelong passion for all things eatable and a love of perfecting simple fresh ingredients makes every item on our breakfast menu just what you want in the morning. Yes, that’s right – you actually get a menu once you sit down after hitting the continental breakfast items, so as not to waste even a precious second before getting a cup of coffee racing to your brain. Every week someone comments on how our omelet is the best they have ever had (fluffy eggs, filled with perfectly grilled ingredients, caramelized cheese, and large enough for even the heftiest of appetites). We even have a breakfast special every morning and can accommodate even the strictest diet. Macrobiotic vegan that wants nothing heated with electric? No problem!

We are proud to say we have the privacy of a hotel with the comforts of home. All our rooms have private bathrooms, 3 with whirlpool tubs and most with radiant floor heat. We are also the only B&B in Chicago to offer a steam room AND a wet-sauna. In fact, to the best of my knowledge, not a single hotel in Chicago (even if they have a steam room or a wet-sauna) allows you to use it free of charge. In the era of nickel & diming customers ($4.50 for a bottle of water we all know we can get from Costco for under a dime – PAAlease), we offer FREE bottled water, coffee, tea, snacks, use of steam room and wet-sauna, WiFi and FREE PARKING! Hotels in downtown Chicago charge between $45 – $60 per night just for parking.

Besides a friendly crack staff that makes sure every detail is taken care of, we happen to be in the heart of the Wicker Park / Bucktown neighborhood, one of Chicago’s most vibrant neighborhoods, more than 80 restaurants, unique boutiques & shops, spas and neighborhood bars all within walking distance.

We are easy to get to either by public transportation (6 blocks away from the /Blue Line Western stop) or by car (we are 2 blocks off I-90/94 Kennedy Expressway).

PLUS! It is about to get much more interesting around here with my upcoming purchase of a farm in Galena, IL where I will be starting an organic, permaculture farm & dog-friendly nature B&B, to be named Galena Del Ray.

Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
Running any business is overcoming obstacles & challenges. Running a business out of your home is even more challenging. I have been fortunate to live in a city where, even though it is large & bureaucratic, Chicago supports their small businesses, and my local alderman, Scott Waguespack has been extremely helpful getting through the bureaucracy.

On the opposite side of the City of Chicago, unfortunately we are also in Cook County where the local County Assessor Joe Berrios has been on a 3 year person attack against B&Bs because one of our former owners, newscaster Andy Shaw pointed out Assessors Joe Berrios’s receiving the majority of his campaign funds from tax appeal lawyers. All this while refusing to correct a corrupt appraisal system (see this story in last week’s Economist:

Ray’s Bucktown Bed and Breakfast of Chicago – what should we know? What do you guys do best? What sets you apart from the competition?
Ray’s B&B is located in Chicago’s vibrant Bucktown/Wicker Park neighborhood, 12 minutes to downtown by train. Modeled after small European hotels, we have 11 unique bedrooms, (each with a private bathroom, WIFI, TV, DVR & robes), free parking, a business center (copier, fax, & computer), steam room, sauna, laundry facility, and comfortable community areas.

Price includes our highly acclaimed full breakfasts cooked-to-order from a menu, including options for vegetarian or other dietary needs. If you’re not an early morning person, you’re in luck—Ray’s serves breakfast when you want it. Coffee, tea and bottled water are free all day.

Ray’s is within walking distance of more than 80 restaurants, unique boutiques & shops, spas and neighborhood bars. We are only a 6-block walk to the Blue Line “L” train to Downtown or O’Hare Airport or to Midway with an easy transfer. By car, we are 2 blocks off I-90/94 (Kennedy Expressway).


  • Rooms range from $139 – $229 and include our highly acclaimed full breakfasts cooked-to-order.
  • Prices include free bottled water, coffee, tea, use of our sauna and our steam-room and parking!

Contact Info:

Getting in touch: VoyageChicago is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

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