Chicago vs Maui County
Illinois Legal but Limited | Hawaii Effectively Banned
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | Maui County, Hawaii |
|---|---|---|
| Legality Status | Legal but Limited | Effectively Banned |
| Permit Fee | $250 annual registration fee | Set by annual budget ordinance — contact Planning Dept for current amount |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | ~18% combined (11% state TAT + 3% county MCTAT + 4% GET) |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Annual |
| Platform Remits Taxes | Yes | No — host must remit |
| Max Fine Example | $1,500–$5,000 per offense; each day is a separate offense | $20,000 first offense; $10,000/day thereafter |
| Verdict | Chicago 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
Maui County, Hawaii
Status Effectively Banned
Permit Fee Set by annual budget ordinance — contact Planning Dept for current amount
Tax Rate ~18% combined (11% state TAT + 3% county MCTAT + 4% GET)
Day Limit No limit
Renewal Annual
Platform Tax No
Max Fine $20,000 first offense; $10,000/day thereafter
Chicago 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 →Maui County Overview
Ordinance 5909 (signed Dec 2025) phases out all apartment-zoned vacation rentals — STR use must cease by Jan 1, 2029 in West Maui and Jan 1, 2031 elsewhere. Existing STRH and B&B permits remain but are capped. Legal challenges are pending.
Full Maui County guide →Frequently Asked Questions
Is it easier to Airbnb in Chicago or Maui County?
Chicago is classified as "Legal but Limited" while Maui County is "Effectively Banned." Chicago's permit fee is $250 annual registration fee compared to Set by annual budget ordinance — contact Planning Dept for current amount in Maui County.
Which city has higher STR taxes — Chicago or Maui County?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while Maui County charges ~18% combined (11% state TAT + 3% county MCTAT + 4% GET). 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. Maui County: $20,000 first offense; $10,000/day thereafter.