Chicago vs Key West

Illinois Legal but Limited | Florida Restricted

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
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.

Permits & Licensing

Chicago charges $250 annual registration fee for STR licensing, while Key West charges $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee. Chicago renewal is annual, and Key West renewal is annual. Overall, Chicago has a more permissive regulatory environment (Legal but Limited) compared to Key West (Restricted).

Tax Obligations

In Chicago, hosts pay 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County. In Key West, hosts pay 12.5% combined (5% county tourist dev. + 7.5% state sales). 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 Key West, violations can result in Up to $5,000/violation and 60 days imprisonment; each day is separate. 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 →

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.

Contact: Key West Licensing Division — (305) 809-3959

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. Overall, Chicago has a more host-friendly regulatory environment.
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).
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. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Chicago and Key West have day limits for Airbnb?
Chicago has no annual day limit. Key West has no annual day limit.
Which city is better for first-time Airbnb hosts — Chicago or Key West?
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. Key West charges $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee with 12.5% combined (5% county tourist dev. + 7.5% state sales). Automatic tax collection in Chicago and Key West makes compliance easier for beginners.