Chicago vs Scottsdale
Illinois Legal but Limited | Arizona Legal with Permit
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | Scottsdale, Arizona |
|---|---|---|
| Legality Status | Legal but Limited | Legal with Permit |
| Permit Fee | $250 annual registration fee | $250/year |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | ~14.27% combined transient occupancy tax (state + county + city) |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Annual |
| Platform Remits Taxes | Yes | Yes |
| Max Fine Example | $1,500–$5,000 per offense; each day is a separate offense | $500 first violation; $1,000 second; $3,500 third; license suspension after 3 in 12 months |
| Verdict | Scottsdale has more favorable STR regulations overall. | |
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.
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.
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.
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.
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). Compare the full breakdown in the table above.
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.