Airbnb Property Management Chicago

Contact Us

Chicago Airbnb Property Management will be easier than ever.

We take care of the entire short term rental management process!

Our approach to Chicago short term rental property management is analytical, hospitality-driven, and owner-friendly. Guestable’s short term rental managers will ensure you and your property are in good hands.

Listings Across Multiple Short Term Rental Platforms

short term vacation rental management
airbnb property management services
short term rentals
airbnb management company

Chicago Short Term Rental Management 


Chicago is one of the top markets for vacation rentals,

short term rentals, and monthly executive rentals given its popularity both nationally and internationally. This popularity has experienced growth in recent years as more people choose to take short term and extended vacations in Chicago. Compared to other major population centers in the country, Chicago has a very favorable regulatory approach to vacation rentals due to the importance of tourism to its economic growth. The increase in remote work has also contributed to more people choosing to spend more time in Chicago.

Given the size of Chicago, there is demand for short term rentals throughout the many neighborhoods of the beautiful city. In neighborhoods with less demand, there tends to be a balancing effect of lower supply. This ensures consistent occupancy no matter where or when a host is renting. Demand in the downtown core is always the strongest due to proximity to restaurants, activities, and sites. Outside of the downtown core, neighbourhoods where tourism isn’t popular, have a lack of hotels. However, their hosts offer great hotel alternatives on sites like Airbnb and experience strong occupancy.

The Chicago short term rental market is seasonal due to variability in travel demand throughout the year. The strongest months of the year are between May and October. And the summer months are the busiest time. Factors like increased tourism, conferences and events generate demand in summer. In the winter months, there is lower demand for tourism. But hosts renting their homes in these months still get a stable monthly income and occupancy.

In the City of Chicago, a short term rental is part or all of a home that hosts rent out to guests for temporary occupancy. The three categories of a short term rental are shared housing units, vacation rentals and bed and breakfasts. For any questions about the Chicago short term rental regulations or vacation rental license, you can visit the city’s website, or contact us.

airbnb property management services

Short Term Property Management

Airbnb Management & Optimization

vacation rental property management


Stephanie is a top Airbnb host

Guestable has enabled Stephanie to rent out her home on Airbnb and other short term rental platforms without having to worry about day to day management.

Airbnb property management

We operate on vacation rental management commission only, we don’t get paid unless you do.

Please provide more information about your property so we can provide you with a short term rental earnings estimate and a quote for our property management and Airbnb listing management services.


Developing an optimized Airbnb listing is as much of an art as it is a science. There are so many Read more
Exceptional guest reviews are the foundation of any strong Airbnb listing. Nothing will make your listing more visible, attract higher Read more
The short term rental market in Toronto is one of the best in North America. With travel demand stronger than Read more
Leverage our experience

Learn how we’ve helped homeowners like you get the most from their property!

Get Started