Asheville vs Chicago
North Carolina Restricted | Illinois Legal but Limited
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Asheville, North Carolina | Chicago, Illinois |
|---|---|---|
| Legality Status | Restricted | Legal but Limited |
| Permit Fee | $200 homestay permit fee | $250 annual registration fee |
| Tax Rate | ~16.75% combined (4.75% state sales + 6% county occupancy + 6% city occupancy) | 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 | Yes | Yes |
| Max Fine Example | $500/day for violations | $1,500–$5,000 per offense; each day is a separate offense |
| Verdict | Chicago has more favorable STR regulations overall. | |
Asheville, North Carolina
Status Restricted
Permit Fee $200 homestay permit fee
Tax Rate ~16.75% combined (4.75% state sales + 6% county occupancy + 6% city occupancy)
Day Limit No limit
Renewal Annual
Platform Tax Yes
Max Fine $500/day for violations
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.
Asheville Overview
Whole-dwelling STRs banned in most zones since 2018; only allowed in resort zoning districts. Owner-occupied homestays (max 2 guest rooms, host must live on-site) are permitted in residential zones with a permit.
Full Asheville 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 Asheville or Chicago?
Asheville is classified as "Restricted" while Chicago is "Legal but Limited." Asheville's permit fee is $200 homestay permit fee compared to $250 annual registration fee in Chicago.
Which city has higher STR taxes — Asheville or Chicago?
Asheville charges ~16.75% combined (4.75% state sales + 6% county occupancy + 6% city occupancy), 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?
Asheville: $500/day for violations. Chicago: $1,500–$5,000 per offense; each day is a separate offense.