Chicago vs Honolulu

Illinois Legal but Limited | Hawaii Restricted

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
Honolulu, Hawaii
Status Restricted
Permit Fee $1,000 initial registration; $500 annual renewal
Tax Rate ~18.5% combined (11% state TAT + 3% county TAT surcharge + 4.5% GET)
Day Limit No limit
Renewal Annual
Platform Tax No
Max Fine $10,000/day for recurring violations; $5,000 initial fine

Chicago has more favorable STR regulations overall.

Permits & Licensing

Chicago charges $250 annual registration fee for STR licensing, while Honolulu charges $1,000 initial registration; $500 annual renewal. Chicago renewal is annual, and Honolulu renewal is annual. Overall, Chicago has a more permissive regulatory environment (Legal but Limited) compared to Honolulu (Restricted).

Tax Obligations

In Chicago, hosts pay 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County. In Honolulu, hosts pay ~18.5% combined (11% state TAT + 3% county TAT surcharge + 4.5% GET). A key difference: platforms like Airbnb automatically collect taxes in Chicago, but hosts in Honolulu 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 Honolulu, violations can result in $10,000/day for recurring violations; $5,000 initial fine. 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 →

Honolulu Overview

STRs limited to resort-zoned and eligible apartment-zoned areas. Hosts must register as B&B (owner-occupied, max 2 guest rooms) or TVU (whole-home in eligible zones). Registrations are non-transferable.

Contact: Dept. of Planning and Permitting — (808) 768-7887

Full Honolulu guide →

Frequently Asked Questions

Is it easier to Airbnb in Chicago or Honolulu?
Chicago is classified as "Legal but Limited" while Honolulu is "Restricted." Chicago's permit fee is $250 annual registration fee compared to $1,000 initial registration; $500 annual renewal in Honolulu. Overall, Chicago has a more host-friendly regulatory environment.
Which city has higher STR taxes — Chicago or Honolulu?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while Honolulu charges ~18.5% combined (11% state TAT + 3% county TAT surcharge + 4.5% GET). Notably, Chicago benefits from automatic platform tax collection, while hosts in Honolulu 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. Honolulu: $10,000/day for recurring violations; $5,000 initial fine. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Chicago and Honolulu have day limits for Airbnb?
Chicago has no annual day limit. Honolulu has no annual day limit.
Which city is better for first-time Airbnb hosts — Chicago or Honolulu?
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. Honolulu charges $1,000 initial registration; $500 annual renewal with ~18.5% combined (11% state TAT + 3% county TAT surcharge + 4.5% GET). Automatic tax collection in Chicago makes compliance easier for beginners.