Chicago vs Washington DC
Illinois Legal but Limited | District of Columbia Legal but Limited
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | Washington DC, District of Columbia |
|---|---|---|
| Legality Status | Legal but Limited | Legal but Limited |
| Permit Fee | $250 annual registration fee | $104.50 for 2-year license |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | 14.5% combined (sales tax on accommodations + transient lodging 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 | $500 first violation; $2,000 second; $6,000 third + license revocation |
| 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
Washington DC, District of Columbia
Status Legal but Limited
Permit Fee $104.50 for 2-year license
Tax Rate 14.5% combined (sales tax on accommodations + transient lodging tax)
Day Limit 90 days/year
Renewal Every 2 years
Platform Tax Yes
Max Fine $500 first violation; $2,000 second; $6,000 third + license revocation
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 →Washington DC Overview
Primary residence only (must qualify for Homestead Deduction). Hosted stays have no day cap. Vacation rentals (unhosted) capped at 90 nights/year. Must carry $250K liability insurance.
Full Washington DC guide →Frequently Asked Questions
Is it easier to Airbnb in Chicago or Washington DC?
Chicago is classified as "Legal but Limited" while Washington DC is "Legal but Limited." Chicago's permit fee is $250 annual registration fee compared to $104.50 for 2-year license in Washington DC.
Which city has higher STR taxes — Chicago or Washington DC?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while Washington DC charges 14.5% combined (sales tax on accommodations + transient lodging 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. Washington DC: $500 first violation; $2,000 second; $6,000 third + license revocation.