Welcome To Chicago Guest House: 
Luxury Vacation Rentals In Chicago

Nightly, Weekly & Monthly Short-Term Stays

Chicago Guest House Vacation Rental Airbnb in Chicago Dining room with paintings on the wall


​​We have six unique 2, 3 & 5 bedroom Wrigleyville Guest Houses.  Each of our Chicago vacation rentals is distinctive, warm & inviting---boasting of charm and character you won't find anywhere else! All comfortably furnished & fully equipped with everything you need to feel at home while visiting Chicago.  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 homes will exceed your expectations--that is our promise! 
statue of harry carey at wrigley field

Explore Lakeview's Wrigleyville


A Lively, Vibrant & Family Friendly Community

The neighborhood has Chicago's greatest concentrations of entertainment, live  theatre  and dining attractions .​​​  It's no wonder locals and visitors alike flock here for a taste of something unique and special! Though you might find you never want to leave the neighborhood, it would be a shame to miss out on everything this amazing city has to offer . Jump on either the brown or red line train---both are direct to downtown and all of the city's most sought-after attractions.  Gather your family and friends & start planning an unforgettable get-a-way at Chicago Guest House!
Millennium Park the Bean
Sue at the Field Museum
Wendella tour boat

Exploring Chicago

​​ So much to do....so little time!  Attractions around every corner---art, music, history, architecture--the list goes on! You'll find fun and interesting things to do every day of the year. 
Red brick homes

Chicago Guest House for Your Short-Term Housing Needs

Winter Monthly Rentals Starting at $99 Night
Being away from home for an extended period can be difficult.  Especially disenchanting when your housing options are the typical cookie-cutter corporate rental apartments.  Chicago Guest House is different! Our uniquely furnished executive suites are full of charm & character, warm and welcoming and each is fully equipped with everything you could possibly need to make your extended stay more than comfortable.  If that's not enough---our location couldn't be better!  We're right in the heart of Wrigleyville ---a lively and vibrant northside neighborhood that represents one of the city’s greatest concentrations of live theater, entertainment and dining attractions. Highly walkable ---shopping, grocery, spas, fitness facilities and more all within steps of our properties; no need for a car.  Arrive with nothing more than your suitcase; we'll take care of the rest! 

Short-Term Rental | Extended Stay  | Corporate Housing  | Relocation | Disaster Relief.  We have you covered!