Chicago vs Maui County

Illinois Legal but Limited | Hawaii Effectively Banned

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
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.

Permits & Licensing

Chicago charges $250 annual registration fee for STR licensing, while Maui County charges Set by annual budget ordinance — contact Planning Dept for current amount. Chicago renewal is annual, and Maui County renewal is annual. Overall, Chicago has a more permissive regulatory environment (Legal but Limited) compared to Maui County (Effectively Banned).

Tax Obligations

In Chicago, hosts pay 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County. In Maui County, hosts pay ~18% combined (11% state TAT + 3% county MCTAT + 4% GET). A key difference: platforms like Airbnb automatically collect taxes in Chicago, but hosts in Maui County must collect and remit taxes themselves — a significant operational burden.

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 Maui County, violations can result in $20,000 first offense; $10,000/day thereafter. 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 →

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.

Contact: Planning Dept., Current Planning Division — (808) 270-8205

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. Overall, Chicago has a more host-friendly regulatory environment.
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). Notably, Chicago benefits from automatic platform tax collection, while hosts in Maui County must handle taxes themselves.
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. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Chicago and Maui County have day limits for Airbnb?
Chicago has no annual day limit. Maui County has no annual day limit.
Which city is better for first-time Airbnb hosts — Chicago or Maui County?
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. Maui County charges Set by annual budget ordinance — contact Planning Dept for current amount with ~18% combined (11% state TAT + 3% county MCTAT + 4% GET). Automatic tax collection in Chicago makes compliance easier for beginners.