Chicago vs Key West
Illinois Legal but Limited | Florida Restricted
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | Key West, Florida |
|---|---|---|
| Legality Status | Legal but Limited | Restricted |
| Permit Fee | $250 annual registration fee | $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | 12.5% combined (5% county tourist dev. + 7.5% state sales) |
| 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 | Up to $5,000/violation and 60 days imprisonment; each day is separate |
| 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
Key West, Florida
Status Restricted
Permit Fee $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee
Tax Rate 12.5% combined (5% county tourist dev. + 7.5% state sales)
Day Limit No limit
Renewal Annual
Platform Tax Yes
Max Fine Up to $5,000/violation and 60 days imprisonment; each day is separate
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 →Key West Overview
Moratorium on new transient rental licenses — only grandfathered properties may operate STRs under 28 days. Existing licenses are property-specific and command $400K+ on the secondary market. Florida DBPR state license also required.
Full Key West guide →Frequently Asked Questions
Is it easier to Airbnb in Chicago or Key West?
Chicago is classified as "Legal but Limited" while Key West is "Restricted." Chicago's permit fee is $250 annual registration fee compared to $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee in Key West.
Which city has higher STR taxes — Chicago or Key West?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while Key West charges 12.5% combined (5% county tourist dev. + 7.5% state sales). 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. Key West: Up to $5,000/violation and 60 days imprisonment; each day is separate.