Chicago vs Honolulu
Illinois Legal but Limited | Hawaii Restricted
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | Honolulu, Hawaii |
|---|---|---|
| Legality Status | Legal but Limited | Restricted |
| Permit Fee | $250 annual registration fee | $1,000 initial registration; $500 annual renewal |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | ~18.5% combined (11% state TAT + 3% county TAT surcharge + 4.5% 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 | $10,000/day for recurring violations; $5,000 initial fine |
| 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
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.
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 →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.
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.
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). 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. Honolulu: $10,000/day for recurring violations; $5,000 initial fine.