Wrigleyville Guest House: Vacation Rentals in Chicago

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​​ We have three Wrigleyville Guest Houses -- The Chicago Guest house on Lakewood, the Guest House on Newport and the third Guest House on Henderson St.; each available for short-term stays or short vacation get-a-ways.  ​​

Wrigleyville is one of the city's most sought after neighborhoods ---a lively and vibrant, family friendly location that represents one of the city’s greatest concentrations of live theater, entertainment and dining attractions.   The historic Greystone homes are located on quiet tree-line streets yet only steps from all the energy & excitement of this amazing neighborhood.  You get the best of both worlds staying here---to the east is Clark Street where you'll find an unlimited selection of restaurants, sports bars, theater and of course Wrigley Field. A few blocks to the west is the Southport Corridor---a 1 mile strip of high end shops, unique boutiques and more wonderful dining options . So come see for yourself what everyone is raving about in Wrigleyville!
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OUR PROPERTIES

Guest House on 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 
Guest House on Newport Avenue
2 Suites
3 Bedrooms | 2 Bathrooms | Sleeps 4-8 
3 Bedrooms | 1 Bathroom  | Sleeps 4-6 
Guest House on Henderson Street
1 Suite
2 Bedrooms | 1 Bathroom | Sleeps 2-4 
 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.​​
shops on Southport Ave in Chicago
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.  

crowds at Wrigley Field 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! 
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

What You'll Experience Staying in Wrigleyville 

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!