Chicago vs Pittsburgh
Illinois Legal but Limited | Pennsylvania Legal with Permit
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | Pittsburgh, Pennsylvania |
|---|---|---|
| Legality Status | Legal but Limited | Legal with Permit |
| Permit Fee | $250 annual registration fee | $35.50/unit ($16 registration + $5.50 inspection + $14 dwelling unit inspection) |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | 13% combined (7% Allegheny County hotel tax + 6% state hotel occupancy tax) |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Annual |
| Platform Remits Taxes | Yes | Yes |
| Max Fine Example | $1,500–$5,000 per offense; each day is a separate offense | $500/unit/month for operating without permit |
| Verdict | Pittsburgh 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
Pittsburgh, Pennsylvania
Status Legal with Permit
Permit Fee $35.50/unit ($16 registration + $5.50 inspection + $14 dwelling unit inspection)
Tax Rate 13% combined (7% Allegheny County hotel tax + 6% state hotel occupancy tax)
Day Limit No limit
Renewal Annual
Platform Tax Yes
Max Fine $500/unit/month for operating without permit
Pittsburgh 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 →Pittsburgh Overview
Rental Permit Program launched December 2024. No day caps or per-owner unit limits. All rental properties must register and pass inspection.
Full Pittsburgh guide →Frequently Asked Questions
Is it easier to Airbnb in Chicago or Pittsburgh?
Chicago is classified as "Legal but Limited" while Pittsburgh is "Legal with Permit." Chicago's permit fee is $250 annual registration fee compared to $35.50/unit ($16 registration + $5.50 inspection + $14 dwelling unit inspection) in Pittsburgh.
Which city has higher STR taxes — Chicago or Pittsburgh?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while Pittsburgh charges 13% combined (7% Allegheny County hotel tax + 6% state hotel 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. Pittsburgh: $500/unit/month for operating without permit.