Chicago vs Portland
Illinois Legal but Limited | Oregon Legal but Limited
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | Portland, Oregon |
|---|---|---|
| Legality Status | Legal but Limited | Legal but Limited |
| Permit Fee | $250 annual registration fee | $65 (Type A single dwelling); $105 (Type A multi-dwelling) |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | 11.5% Transient Lodging Tax (6% city + 5.5% county) + 3% TID + 1.5% state |
| Annual Day Limit | No limit | No limit |
| 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 | Up to $26,201 across five violation types; permit revocation with 2-year ban |
| 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
Portland, Oregon
Status Legal but Limited
Permit Fee $65 (Type A single dwelling); $105 (Type A multi-dwelling)
Tax Rate 11.5% Transient Lodging Tax (6% city + 5.5% county) + 3% TID + 1.5% state
Day Limit No limit
Renewal Every 2 years
Platform Tax Yes
Max Fine Up to $26,201 across five violation types; permit revocation with 2-year ban
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 →Portland Overview
Only accessory (hosted) short-term rentals allowed; resident must occupy the dwelling at least 270 days/year. Type A permits allow up to 2 bedrooms and 5 guests. Whole-home unhosted rentals are prohibited.
Full Portland guide →Frequently Asked Questions
Is it easier to Airbnb in Chicago or Portland?
Chicago is classified as "Legal but Limited" while Portland is "Legal but Limited." Chicago's permit fee is $250 annual registration fee compared to $65 (Type A single dwelling); $105 (Type A multi-dwelling) in Portland.
Which city has higher STR taxes — Chicago or Portland?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while Portland charges 11.5% Transient Lodging Tax (6% city + 5.5% county) + 3% TID + 1.5% state. 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. Portland: Up to $26,201 across five violation types; permit revocation with 2-year ban.