Chicago vs Orlando
Illinois Legal but Limited | Florida Restricted
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | Orlando, Florida |
|---|---|---|
| Legality Status | Legal but Limited | Restricted |
| Permit Fee | $250 annual registration fee | $100 city permit + state DBPR license |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | 12.5% (6% state + 6% county tourist dev. + 0.5% city) |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Annual (city); Biennial (state) |
| Platform Remits Taxes | Yes | Yes |
| Max Fine Example | $1,500–$5,000 per offense; each day is a separate offense | $250–$500/day for code violations |
| Verdict | Chicago 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
Orlando, Florida
Status Restricted
Permit Fee $100 city permit + state DBPR license
Tax Rate 12.5% (6% state + 6% county tourist dev. + 0.5% city)
Day Limit No limit
Renewal Annual (city); Biennial (state)
Platform Tax Yes
Max Fine $250–$500/day for code violations
Chicago 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 →Orlando Overview
STRs are prohibited in most single-family residential zoning districts. Allowed in tourist-commercial zones and some mixed-use areas. Florida state law preempts local bans enacted after June 2011, creating a complex legal landscape.
Full Orlando guide →Frequently Asked Questions
Is it easier to Airbnb in Chicago or Orlando?
Chicago is classified as "Legal but Limited" while Orlando is "Restricted." Chicago's permit fee is $250 annual registration fee compared to $100 city permit + state DBPR license in Orlando.
Which city has higher STR taxes — Chicago or Orlando?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while Orlando charges 12.5% (6% state + 6% county tourist dev. + 0.5% 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. Orlando: $250–$500/day for code violations.