Chicago vs San Francisco
Illinois Legal but Limited | California Legal but Limited
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | San Francisco, California |
|---|---|---|
| Legality Status | Legal but Limited | Legal but Limited |
| Permit Fee | $250 annual registration fee | $450 registration fee |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | 14% Transient Occupancy Tax |
| Annual Day Limit | No limit | 90 days/year |
| Renewal Interval | Annual | Every 2 years |
| Platform Remits Taxes | Yes | Yes |
| Max Fine Example | $1,500–$5,000 per offense; each day is a separate offense | $1,000/day for illegal hosting |
| Verdict | Both cities have comparable STR regulatory environments. | |
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 Francisco, California
Status Legal but Limited
Permit Fee $450 registration fee
Tax Rate 14% Transient Occupancy Tax
Day Limit 90 days/year
Renewal Every 2 years
Platform Tax Yes
Max Fine $1,000/day for illegal hosting
Both cities have comparable STR regulatory environments.
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 Francisco Overview
Primary residence only, with a 90-day cap on unhosted stays (unlimited for hosted stays). Hosts must register, carry $500K liability insurance, and pass a fire/safety inspection. Rent-controlled units face additional restrictions.
Full San Francisco guide →Frequently Asked Questions
Is it easier to Airbnb in Chicago or San Francisco?
Chicago is classified as "Legal but Limited" while San Francisco is "Legal but Limited." Chicago's permit fee is $250 annual registration fee compared to $450 registration fee in San Francisco.
Which city has higher STR taxes — Chicago or San Francisco?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while San Francisco charges 14% Transient Occupancy Tax. 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 Francisco: $1,000/day for illegal hosting.