Charleston vs Chicago
South Carolina Restricted | Illinois Legal but Limited
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Charleston, South Carolina | Chicago, Illinois |
|---|---|---|
| Legality Status | Restricted | Legal but Limited |
| Permit Fee | $250 (24–72 nights/yr) or $1,500 (72+ nights/yr) + $200 zoning review fee | $250 annual registration fee |
| Tax Rate | ~14% combined (5% state sales + 2% state accommodations + 2% county + 2% city + local option taxes) | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Annual |
| Platform Remits Taxes | No — host must remit | Yes |
| Max Fine Example | Up to $1,087/day or 30 days jail; criminal prosecution possible | $1,500–$5,000 per offense; each day is a separate offense |
| Verdict | Chicago has more favorable STR regulations overall. | |
Charleston, South Carolina
Status Restricted
Permit Fee $250 (24–72 nights/yr) or $1,500 (72+ nights/yr) + $200 zoning review fee
Tax Rate ~14% combined (5% state sales + 2% state accommodations + 2% county + 2% city + local option taxes)
Day Limit No limit
Renewal Annual
Platform Tax No
Max Fine Up to $1,087/day or 30 days jail; criminal prosecution possible
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
Chicago has more favorable STR regulations overall.
Charleston Overview
Whole-house STRs are effectively banned; at least one full-time resident must sleep on-site each night. Max 4 adult guests. Charleston is one of the few U.S. cities that criminally prosecutes illegal STR operators. $1M liability insurance required.
Full Charleston guide →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 →Frequently Asked Questions
Is it easier to Airbnb in Charleston or Chicago?
Charleston is classified as "Restricted" while Chicago is "Legal but Limited." Charleston's permit fee is $250 (24–72 nights/yr) or $1,500 (72+ nights/yr) + $200 zoning review fee compared to $250 annual registration fee in Chicago.
Which city has higher STR taxes — Charleston or Chicago?
Charleston charges ~14% combined (5% state sales + 2% state accommodations + 2% county + 2% city + local option taxes), while Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County. Compare the full breakdown in the table above.
Which city has stricter fines for illegal short-term rentals?
Charleston: Up to $1,087/day or 30 days jail; criminal prosecution possible. Chicago: $1,500–$5,000 per offense; each day is a separate offense.