Chicago vs Philadelphia
Illinois Legal but Limited | Pennsylvania Legal with Permit
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | Philadelphia, Pennsylvania |
|---|---|---|
| Legality Status | Legal but Limited | Legal with Permit |
| Permit Fee | $250 annual registration fee | $50 Limited Lodging license |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | 8.5% Hotel Tax + sales tax |
| Annual Day Limit | No limit | 180 days/year |
| Renewal Interval | Annual | Annual |
| Platform Remits Taxes | Yes | Yes |
| Max Fine Example | $1,500–$5,000 per offense; each day is a separate offense | $300/day for unlicensed rental |
| Verdict | Philadelphia 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
Philadelphia, Pennsylvania
Status Legal with Permit
Permit Fee $50 Limited Lodging license
Tax Rate 8.5% Hotel Tax + sales tax
Day Limit 180 days/year
Renewal Annual
Platform Tax Yes
Max Fine $300/day for unlicensed rental
Philadelphia 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 →Philadelphia Overview
Limited Lodging license required. Primary residence only, capped at 180 days/year for unhosted rentals. Hosted (owner-present) stays have no day cap. Must carry liability insurance.
Full Philadelphia guide →Frequently Asked Questions
Is it easier to Airbnb in Chicago or Philadelphia?
Chicago is classified as "Legal but Limited" while Philadelphia is "Legal with Permit." Chicago's permit fee is $250 annual registration fee compared to $50 Limited Lodging license in Philadelphia.
Which city has higher STR taxes — Chicago or Philadelphia?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while Philadelphia charges 8.5% Hotel Tax + sales 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. Philadelphia: $300/day for unlicensed rental.