Chicago vs Tampa
Illinois Legal but Limited | Florida Legal with Permit
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | Tampa, Florida |
|---|---|---|
| Legality Status | Legal but Limited | Legal with Permit |
| Permit Fee | $250 annual registration fee | $50 DBPR application + $170/year state license; county Business Tax Receipt required |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | ~13.5% combined (6% county tourist dev. + 6% state sales + 1.5% surtax) |
| 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 | Daily compounding fines for violations; amounts vary by infraction |
| Verdict | Tampa 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
Tampa, Florida
Status Legal with Permit
Permit Fee $50 DBPR application + $170/year state license; county Business Tax Receipt required
Tax Rate ~13.5% combined (6% county tourist dev. + 6% state sales + 1.5% surtax)
Day Limit No limit
Renewal Annual
Platform Tax Yes
Max Fine Daily compounding fines for violations; amounts vary by infraction
Tampa 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 →Tampa Overview
No city-specific STR ordinance — state DBPR license and county Business Tax Receipt are primary requirements. Florida's 2011 preemption law limits local restrictions. STRs generally allowed in commercial and mixed-use zones.
Full Tampa guide →Frequently Asked Questions
Is it easier to Airbnb in Chicago or Tampa?
Chicago is classified as "Legal but Limited" while Tampa is "Legal with Permit." Chicago's permit fee is $250 annual registration fee compared to $50 DBPR application + $170/year state license; county Business Tax Receipt required in Tampa.
Which city has higher STR taxes — Chicago or Tampa?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while Tampa charges ~13.5% combined (6% county tourist dev. + 6% state sales + 1.5% surtax). 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. Tampa: Daily compounding fines for violations; amounts vary by infraction.