About Chicago Guest House

Chicago Guest House is a set of three unique guest houses in the lively neighborhood of Wrigleyville in Chicago, Illinois.  I am a Chicago native, who left a successful career in sales to create unique vacation rentals on the north end of the city. My goal was to provide a real alternative to major hotels-- a refuge for those looking for the distinction, intimacy, class and comfort that a hotel cannot provide. 

​The first property to open for business was on Henderson Street in early 2004. Lakewood Avenue, the largest property, opened later the same year and lastly the Newport Avenue location in 2006--the most family friendly of my guest houses. Each property offers unique benefits; ask me for tips and information if you’re not sure which home is most suitable for your needs.  
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I personally decorated all the homes and filled them with souvenirs and artifacts I have gathered over the years, so they are continually evolving the way a real ‘home’ should.  You will see that each is hung throughout with original art either by myself or by some of my favorite local artists---some interesting, others unusual and even humorous, but never dull!

Spacious inside and out---all three properties have beautiful gardens that provide havens of calm from the hustle and bustle of the city.  All of the guest houses have every benefit and convenience (including free parking!) that you could imagine, along with a picturesque character and charm you simply won’t get anywhere else.

I believe your travel experience is not a 'click' or a 'swipe' away. Customer service is my top priority and thus I am always available when you call, text or email and ready to answer any questions you may have. Staying at Chicago Guest House is not just about staying at a vacation rental; it's about experiencing Chicago in the most unforgettable way! I look forward to having you stay!

Teri Smith | Owner | Manager
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Lakewood Avenue
​3 Suites
5 Bedrooms | 2 Bathrooms | Sleeps 6-9
  3 Bedrooms | 2 Bathrooms | Sleeps 4-6  
 3 Bedrooms | 2 Bathrooms | Sleeps 3-6 
Newport Avenue
2 Suites
3 Bedrooms | 2 Bathrooms | Sleeps 4-8 
3 Bedrooms | 1 Bathroom  | Sleeps 4-6 
Henderson Street
1 Suite
2 Bedrooms | 1 Bathroom | Sleeps 2-4