Chicago vs San Antonio
Illinois Legal but Limited | Texas Legal with Permit
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | San Antonio, Texas |
|---|---|---|
| Legality Status | Legal but Limited | Legal with Permit |
| Permit Fee | $250 annual registration fee | Type 1 $300/3 years; Type 2 $450/3 years; $200 application fee |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | 16.75% Hotel Occupancy Tax (6% state + 9% city + 1.75% county) |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Triennial (every 3 years) |
| Platform Remits Taxes | Yes | Yes |
| Max Fine Example | $1,500–$5,000 per offense; each day is a separate offense | Up to $500 per offense; each day is a separate violation; permit revocation up to 3 years |
| Verdict | San Antonio 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 Antonio, Texas
Status Legal with Permit
Permit Fee Type 1 $300/3 years; Type 2 $450/3 years; $200 application fee
Tax Rate 16.75% Hotel Occupancy Tax (6% state + 9% city + 1.75% county)
Day Limit No limit
Renewal Triennial (every 3 years)
Platform Tax Yes
Max Fine Up to $500 per offense; each day is a separate violation; permit revocation up to 3 years
San Antonio 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 Antonio Overview
Two-tier permit system (Type 1 owner-occupied, Type 2 investment). Type 2 STRs capped at 12.5% of housing per blockface; platforms must remove listings without valid permit numbers.
Full San Antonio guide →Frequently Asked Questions
Is it easier to Airbnb in Chicago or San Antonio?
Chicago is classified as "Legal but Limited" while San Antonio is "Legal with Permit." Chicago's permit fee is $250 annual registration fee compared to Type 1 $300/3 years; Type 2 $450/3 years; $200 application fee in San Antonio.
Which city has higher STR taxes — Chicago or San Antonio?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while San Antonio charges 16.75% Hotel Occupancy Tax (6% state + 9% city + 1.75% county). 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 Antonio: Up to $500 per offense; each day is a separate violation; permit revocation up to 3 years.