Lakeview Vacation Rentals From Chicago Guest House

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​​Have you ever wondered what it would be like to live in Chicago even if only a few nights, a week or a few months?  There's no better neighborhood to live like a local than Lakeview!  This northside neighborhood is lively & vibrant  and represents one of the city’s greatest concentrations of live theater, entertainment and dining attractions. ​ This is the largest community in Chicago and is comprised of several smaller more distinct areas which include Wrigleyville, the Southport Corridor, North Halstead (aka 'Boystown'), East Lakeview and the Sheridan Station Corridor. Whether you are a business or leisure traveler, looking for a short-term stay or vacation get-a-way, you're sure to find the Chicago Guest House's in Lakeview  will exceed your expectations--that is our promise!  
Shop on Southport Ave in Chicago
Southport Corridor
2 Blocks to The West 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, 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.    
Wrigleyville & Wrigley Field
3 Blocks to the East of Chicago Guest House
Crowds in front of Wrigley Field in Chicago
​​ 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' neighborhood for people in search of bars, live music & entertainment and dining.  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.  On games day Clark street overflow with the masses of Cubs fans looking to celebrate a WIN!   
Flags in Boystown Neighborhood of Chicago
Boystown |North Halstead
6 Blocks East of Chicago Guest House
​​ The city's Boystown neighborhood is one of the LGBT communities in the United States. Hard not to notice as the buildings and streets here are adorned with colorful pylons & banners. It is here that you will find an outstanding selection of dining options, and a dance scene that can’t be beat----definitely a neighborhood with an energy all its own!   
The area's notable events---the Chicago Pride Parade  and Market Days, attract more than one million spectators and visitors of EVERY background and sexual orientation each summer.  Great food, star music talent and awesome crowds. So much fun!
Belmont Theatre District
Mercury Theater on Southport Ave in Chicago
There are over 50 theaters located within a 1 mile radius, officially makes 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.  
Lakeview's Northern End of Lincoln Park


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