Chicago vs Miami

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
Miami, Florida
Status Restricted
Permit Fee $150 city certificate + state DBPR license fee
Tax Rate 13% (6% state + 5% county tourist dev. + 2% city resort tax)
Day Limit No limit
Renewal Annual (city); Biennial (state)
Platform Tax Yes
Max Fine $20,000 lien per violation by code enforcement

Chicago has more favorable STR regulations overall.

Permits & Licensing

Chicago charges $250 annual registration fee for STR licensing, while Miami charges $150 city certificate + state DBPR license fee. Chicago renewal is annual, and Miami renewal is annual (city); biennial (state). Overall, Chicago has a more permissive regulatory environment (Legal but Limited) compared to Miami (Restricted).

Tax Obligations

In Chicago, hosts pay 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County. In Miami, hosts pay 13% (6% state + 5% county tourist dev. + 2% city resort tax). 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 Miami, violations can result in $20,000 lien per violation by code enforcement. 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 →

Miami Overview

STRs restricted to commercially zoned or mixed-use areas. Single-family residential neighborhoods generally prohibit STRs. State preemption law limits some local regulations. Both city Certificate of Use and state DBPR license required.

Contact: Miami Planning & Zoning — (305) 416-1400

Full Miami guide →

Frequently Asked Questions

Is it easier to Airbnb in Chicago or Miami?
Chicago is classified as "Legal but Limited" while Miami is "Restricted." Chicago's permit fee is $250 annual registration fee compared to $150 city certificate + state DBPR license fee in Miami. Overall, Chicago has a more host-friendly regulatory environment.
Which city has higher STR taxes — Chicago or Miami?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while Miami charges 13% (6% state + 5% county tourist dev. + 2% city resort tax).
Which city has stricter fines for illegal short-term rentals?
Chicago: $1,500–$5,000 per offense; each day is a separate offense. Miami: $20,000 lien per violation by code enforcement. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Chicago and Miami have day limits for Airbnb?
Chicago has no annual day limit. Miami has no annual day limit.
Which city is better for first-time Airbnb hosts — Chicago or Miami?
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. Miami charges $150 city certificate + state DBPR license fee with 13% (6% state + 5% county tourist dev. + 2% city resort tax). Automatic tax collection in Chicago and Miami makes compliance easier for beginners.