Welcome To Chicago Guest House: Luxury Chicago Vacation Rentals In Wrigleyville

Check Availability
​​ We have six unique 2, 3 & 5-bedroom Wrigleyville Guest Houses.  Each one is distinctive, warm & inviting; all comfortably furnished & fully equipped with everything you need to feel at home while visiting Chicago.  For at least 9 months out of the year  you'll take delight in having some outdoor space too!  Our peaceful & lush gardens are the perfect place to gather over coffee, a glass of wine or the dinner you've cooked out on the grill.  Whether you are a business or leisure traveler, looking for a short-term stay or vacation get-a-way, you're sure to find that our Chicago vacation rentals will exceed your expectations--that is my promise!  So, gather your family and friends and start planning an unforgettable get-a-way at Chicago Guest House! 
Call Now!
Email

OUR PROPERTIES

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 

What You'll Experience When Staying at Chicago Guest House 

 Our location couldn't be better!  Lakeview is the largest community in Chicago and comprised of several smaller more distinct areas which include Wrigleyville, the Southport Corridor, North Halstead AKA: 'Boystown', East Lakeview and the Sheridan Station Corridor. This northside neighborhood is lively and vibrant and represents one of the city’s greatest concentrations of live theater, entertainment and dining attractions.
The Southport Corridor of Lakeview
2 Blocks East of Chicago Guest House
Where you can enjoy the festive atmosphere of Wrigleyville without the crowds! It is here that you will find an incredible selection of restaurants , cafés, bars, groceries, and shopping---big name chains & unique boutiques.  Continue to stroll along Belmont Ave, Sheridan and Halstead and you’ll see why Lakeview has the reputation of being the hippest shopping district in Chicago.
“Family friendly” best describes the
Southport Corridor of Lakeview. Southport Avenue is filled with families pushing strollers and walking dogs, sitting at the local café’s and restaurants; many of which have stroller valets, step stools in the bathrooms, and free meals for kids during certain hours of the day.  

shops on Southport Ave in Chicago
​​Wrigleyville | Wrigley Field
3 Blocks from Chicago Guest House
A lively little pocket in the Lakeview neighborhood that surrounds historic Wrigley Field, the second oldest stadium in baseball and home to the beloved Chicago Cubs.  Quiet by day—lively at night. The 'go to' area of Lakeview for people in search of bars, live music & entertainment and dining.  On games day Clark street overflow with the masses of Cubs fans looking to celebrate a WIN! Even if you don't spend the afternoon watching a game, you don't want to miss strolling over to the corner of Clark & Addison to see one of baseball's oldest ballparks nestled among the historic Greystones that make up this amazing neighborhood! 
crowds at Wrigley Field Chicago
Mercury theater in Lakeview Chicago
The Belmont Theatre District
With over 50 theaters located within a 1 mile radius, officially making Lakeview the largest theatre district in Chicago. The BTD offers theater lovers the best of edgy neighborhood theater, the country’s largest concentration of improv theaters, daytime & late-nite shows, adult and all ages shows, standup comedy and dinner theater.  
Live bands r in Lakeview Chicago
The Lakeview music venues and concert halls tops that of any other area in Chicago. Bands travel from around the world to play shows here. Tiny dives with a stage in the back of the bar are just as established in the music scene as the large theaters that seat thousands. 
Restaurants r in Lakeview Chicago
Amazing Restaurants--- Tamales to tiramisu; the dining choices in Lakeivew / Wrigleyville are endless . No matter what you have a 'hankerin' for; you’re sure to find it within walking distance of any of the three Chicago Guest House properties!