Chicago vs San Diego
Illinois Legal but Limited | California Legal with Permit
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | San Diego, California |
|---|---|---|
| Legality Status | Legal but Limited | Legal with Permit |
| Permit Fee | $250 annual registration fee | Tier 1: $226; Tier 2: $317; Tier 3/4: $1,170 (includes application + license) |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | 11.75%–13.75% TOT (varies by zone proximity to Convention Center) |
| Annual Day Limit | No limit | 20 days/year |
| Renewal Interval | Annual | Biennial |
| Platform Remits Taxes | Yes | Yes |
| Max Fine Example | $1,500–$5,000 per offense; each day is a separate offense | $1,000 per violation; criminal misdemeanor charges for continued violations |
| Verdict | San Diego 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
San Diego, California
Status Legal with Permit
Permit Fee Tier 1: $226; Tier 2: $317; Tier 3/4: $1,170 (includes application + license)
Tax Rate 11.75%–13.75% TOT (varies by zone proximity to Convention Center)
Day Limit 20 days/year
Renewal Biennial
Platform Tax Yes
Max Fine $1,000 per violation; criminal misdemeanor charges for continued violations
San Diego 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 →San Diego Overview
Four-tier license system with caps: Tier 3 limited to 1% of housing units; Tier 4 (Mission Beach) capped at 30% and at capacity. Only one license per host; licenses are non-transferable.
Full San Diego guide →Frequently Asked Questions
Is it easier to Airbnb in Chicago or San Diego?
Chicago is classified as "Legal but Limited" while San Diego is "Legal with Permit." Chicago's permit fee is $250 annual registration fee compared to Tier 1: $226; Tier 2: $317; Tier 3/4: $1,170 (includes application + license) in San Diego.
Which city has higher STR taxes — Chicago or San Diego?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while San Diego charges 11.75%–13.75% TOT (varies by zone proximity to Convention Center). 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. San Diego: $1,000 per violation; criminal misdemeanor charges for continued violations.