Chicago, IL Airbnb Market Data: Revenue, Occupancy & ADR

On the product level, Chicago’s investment landscape is anchored by two- and three-bedroom listings, which together account for nearly half the city’s active inventory. Two-bedrooms (1,426 listings) generate an average of $31,783 annually at a $213 ADR and 53% occupancy, while three-bedrooms (822 listings) outperform with $40,180 average annual revenue and a $291 ADR, albeit with slightly lower occupancy at 49%. Investors targeting three-bedroom assets are capturing a meaningful premium on nightly rates and annualized returns, particularly in neighborhoods with strong year-round demand. For tailored acquisition guidance in these segments, connect with a Chalet agent.

Geographically, the city’s highest-performing zip codes are tightly clustered along the North Side and select central neighborhoods. In 60614 (Lincoln Park), median annual revenue reaches $48,100 at a $261 ADR and 57% occupancy, with a 7.9% yield on a $611,060 median home value. The adjacent 60657 (Lakeview) posts $40,960 median revenue, 58% occupancy, and an 8.5% yield on $483,742 homes. Meanwhile, 60616 (South Loop/Chinatown) stands out for yield: $40,789 median revenue and a 13.4% gross yield on a $305,160 home, though occupancy is lower at 44%. These clusters reflect a mix of tourism, business travel, and local demand, and they offer differentiated risk/reward profiles for investors seeking to optimize for yield or asset appreciation. For neighborhood-level underwriting, consult a Chalet agent.

At scale, Chicago’s winners are operators who can navigate regulatory hurdles and capture demand from a mix of drive-market and national guests. Only 5.9% of reviews come from international travelers; most guests originate from the Midwest and major U.S. metros. The average booking lead time is 47 days, with a median stay of 5.9 nights—supporting both leisure and business demand. The market’s fragmentation (3,167 hosts, with the top 10 controlling just 10.4% of supply) means professionalization and compliance are key levers for outperformance. Investors can run scenarios on acquisition, yield, and compliance costs with the Chalet ROI calculator.

Risks are concentrated and real. The most material movement: occupancy is up 24.8% year-over-year, and ADR has climbed 17.6%, both outpacing a modest 2.8% increase in listing supply and a 2.4% rise in home values. These tailwinds are offset by pronounced seasonality—January’s trough is a persistent drag—and by regulatory volatility. Chicago’s STR regime is legal but highly regulated, with a 27.75% tax stack, strict licensing, and ongoing precinct-level amendments that can abruptly restrict operations. Investors must monitor compliance and local zoning closely; review the latest Chicago STR regulations before underwriting any deal.