Chicago, the third-largest city in the United States, attracts millions of tourists, business travellers, and digital nomads every year. As a result, the demand for short term rentals in Chicago has surged, making it an increasingly attractive option for property investors and landlords seeking flexible income streams.
Whether you're a UK-based investor expanding into the US market or a property owner exploring rental models, understanding the landscape of short term rentals in Chicago is essential for success.
Short term rentals — defined as properties rented for fewer than 30 consecutive days — offer several compelling advantages in Chicago:
High Occupancy Rates: Tourist hotspots like The Loop, River North, and Lincoln Park see year-round demand.
Dynamic Pricing Models: Platforms like Airbnb and Vrbo allow landlords to adjust rates for peak seasons and events.
Diversified Tenant Base: Corporate travellers, tourists, and temporary relocators provide a broad and consistent customer base.
Higher Yields: Compared to long-term tenancies, short term rentals often generate higher per-night income.
While the city’s overall market is promising, success heavily depends on choosing the right location. Some of the most sought-after areas include:
Known for its vibrant nightlife, art galleries, and proximity to downtown, River North is ideal for both leisure and business travellers.
As Chicago’s business hub, The Loop is perfect for corporate clients and tourists alike, particularly those attending conferences and events.
Trendy and youthful, these areas attract creatives, digital nomads, and out-of-town visitors seeking a local, authentic experience.
With its family-friendly atmosphere and access to green spaces, Lincoln Park draws longer-stay visitors, making it ideal for mid-term rentals as well.
Unlike many other US cities, Chicago has strict regulations on short term rentals to maintain neighbourhood character and safety. Investors must comply with the following:
Registration Requirement: All short term rentals must be registered with the city and listed on the City of Chicago’s Shared Housing Ordinance portal.
Zoning Restrictions: Certain buildings and zones prohibit or limit short term rental activity.
Platform Compliance: Only approved properties can be listed on platforms like Airbnb or Booking.com.
Host Caps: Hosts may be limited in the number of listings they can operate.
Non-compliance can result in fines, delisting, or even property sanctions — making expert guidance essential.
For UK-based investors, Chicago presents a prime opportunity for international property diversification:
Favourable Exchange Rates: The GBP to USD rate can amplify returns when converted back to sterling.
Property Values: Compared to London, Chicago offers strong value per square foot, especially in growth neighbourhoods.
Legal Structures: Investors can work through LLCs or partnerships for property acquisition and management.
However, navigating US tax laws, licensing, and property management logistics requires expertise and the right local partners.
At Fraser Bond, we work with UK-based and international investors to identify, acquire, and manage short term rental properties in high-yield cities like Chicago.
Our services include:
Sourcing vetted investment properties with short term rental potential
Partnering with trusted US real estate agents and attorneys
Assisting with cross-border legal and financial due diligence
Connecting investors with licensed local property managers
Advising on compliance with local short term rental laws
With Fraser Bond, you gain more than just access to property — you gain a strategic partner to guide your international investment journey.
Chicago’s short term rental market offers dynamic earning potential, especially in well-located properties that meet city regulations. For UK investors or landlords seeking diversification, it represents a compelling blend of opportunity and urban growth — but one that requires careful navigation.
By partnering with a trusted advisor like Fraser Bond, you can capitalise on this trend with confidence and expert support every step of the way.
