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!  The perfect choice for business & leisure travelers looking for a real alternative to major hotels-- a refuge for those looking for the distinction, intimacy, class and comfort that a hotel cannot provide.  All comfortably furnished & fully equipped with everything you need to feel at home while visiting Chicago.  Whether you are 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! 
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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!
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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!
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Building Better Business Relationships
Next time you're in Chicago for a convention; try something different---something more personal. You'll love the experience and your employees and  your customers will too! 
8 peoples arms toasting with white wine
Different ages and ethnic backgrounds dining together under lights.
Living together and more importantly dining together acts as a kind of social glue. Reserch done by Cornell University highlights the value we can gain from dining with our colleagues. The research found that those who ate meals together had significantly better performance and were most effective as a team.
"We closed more deals cooking steaks and drinking beer in the back yard than we ever did entertaining our customers in a hospitality suite. It was like we invited them in to our home. Great experience. We'll never stay anywhere else"
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