Chicago vs Scottsdale

Illinois Legal but Limited | Arizona Legal with Permit

Disclaimer: General information only — not legal advice. Verify with your local government.

Chicago, Illinois
Status Legal but Limited
Permit Fee $250 annual registration fee
Tax Rate 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County
Day Limit No limit
Renewal Annual
Platform Tax Yes
Max Fine $1,500–$5,000 per offense; each day is a separate offense
Scottsdale, Arizona
Status Legal with Permit
Permit Fee $250/year
Tax Rate ~14.27% combined transient occupancy tax (state + county + city)
Day Limit No limit
Renewal Annual
Platform Tax Yes
Max Fine $500 first violation; $1,000 second; $3,500 third; license suspension after 3 in 12 months

Scottsdale has more favorable STR regulations overall.

Permits & Licensing

Chicago charges $250 annual registration fee for STR licensing, while Scottsdale charges $250/year. Chicago renewal is annual, and Scottsdale renewal is annual. Overall, Scottsdale has a more permissive regulatory environment (Legal with Permit) compared to Chicago (Legal but Limited).

Tax Obligations

In Chicago, hosts pay 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County. In Scottsdale, hosts pay ~14.27% combined transient occupancy tax (state + county + city). Both cities benefit from automatic platform tax collection through Airbnb and similar services, simplifying compliance for hosts.

Day Limits & Restrictions

Neither city imposes an annual day limit on short-term rentals, giving hosts year-round flexibility.

Fines & Enforcement

Hosts operating without a permit in Chicago face penalties including $1,500–$5,000 per offense; each day is a separate offense. In Scottsdale, violations can result in $500 first violation; $1,000 second; $3,500 third; license suspension after 3 in 12 months. Both cities actively enforce their STR regulations, so securing proper licensing before listing is essential in either market.

Chicago Overview

Must be host's primary residence; buildings with 5+ units limited to no more than 6 STR units; Restricted Residential Zones and Prohibited Buildings List apply. $1M commercial general liability insurance required.

Contact: Dept. of Business Affairs and Consumer Protection — (312) 744-6060

Full Chicago guide →

Scottsdale Overview

Ordinance 4566 caps occupancy at 6 adults plus dependent children, requires 1 off-street parking space per bedroom, $500K liability insurance, and neighbor notification within 30 days. Special events and commercial uses prohibited.

Contact: Scottsdale Code Enforcement — (480) 312-2546

Full Scottsdale guide →

Frequently Asked Questions

Is it easier to Airbnb in Chicago or Scottsdale?
Chicago is classified as "Legal but Limited" while Scottsdale is "Legal with Permit." Chicago's permit fee is $250 annual registration fee compared to $250/year in Scottsdale. Overall, Scottsdale has a more host-friendly regulatory environment.
Which city has higher STR taxes — Chicago or Scottsdale?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while Scottsdale charges ~14.27% combined transient occupancy tax (state + county + city).
Which city has stricter fines for illegal short-term rentals?
Chicago: $1,500–$5,000 per offense; each day is a separate offense. Scottsdale: $500 first violation; $1,000 second; $3,500 third; license suspension after 3 in 12 months. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Chicago and Scottsdale have day limits for Airbnb?
Chicago has no annual day limit. Scottsdale has no annual day limit.
Which city is better for first-time Airbnb hosts — Chicago or Scottsdale?
For new hosts, consider the total cost of entry: Chicago charges $250 annual registration fee for permits with 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County in taxes. Scottsdale charges $250/year with ~14.27% combined transient occupancy tax (state + county + city). Automatic tax collection in Chicago and Scottsdale makes compliance easier for beginners.