Windy City RE
HospitalityIllinois, United States11-50 Employees
Windy City RE is a hospitality company that manages short-term rental properties, offering a range of accommodations from studios to 6-bedroom houses in Chicago, Nashville, Phoenix, and other cities. The focus is on providing cost-effective, well-designed stays in desirable locations, with an emphasis on modern comforts and guest experience. Based in Chicago, the firm operates within a competitive short-term rental market and serves travelers seeking private, professionally managed housing options. The company is positioned to appeal to guests who require flexible lodging alternatives for leisure or business. It has been associated with Slumber Stay LLC, a name that has faced regulatory scrutiny related to Chicago’s Shared Housing Ordinance, including a formal legal action filed by the City of Chicago in June 2026. This context highlights the regulatory environment and potential compliance considerations for its operations in urban markets.