Boston vs Chicago
Massachusetts Legal but Limited | Illinois Legal but Limited
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Boston, Massachusetts | Chicago, Illinois |
|---|---|---|
| Legality Status | Legal but Limited | Legal but Limited |
| Permit Fee | $25 registration fee | $250 annual registration fee |
| Tax Rate | 6.5% state excise + 6% city convention center tax | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Annual |
| Platform Remits Taxes | Yes | Yes |
| Max Fine Example | $300/day for unregistered listing | $1,500–$5,000 per offense; each day is a separate offense |
| Verdict | Both cities have comparable STR regulatory environments. | |
Boston, Massachusetts
Status Legal but Limited
Permit Fee $25 registration fee
Tax Rate 6.5% state excise + 6% city convention center tax
Day Limit No limit
Renewal Annual
Platform Tax Yes
Max Fine $300/day for unregistered listing
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
Both cities have comparable STR regulatory environments.
Boston Overview
Only primary-residence units may be listed as STRs. Investor-owned (non-owner-occupied) short-term rentals are prohibited. Must register with the city and carry $1M liability insurance.
Full Boston guide →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 →Frequently Asked Questions
Is it easier to Airbnb in Boston or Chicago?
Boston is classified as "Legal but Limited" while Chicago is "Legal but Limited." Boston's permit fee is $25 registration fee compared to $250 annual registration fee in Chicago.
Which city has higher STR taxes — Boston or Chicago?
Boston charges 6.5% state excise + 6% city convention center tax, while Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County. Compare the full breakdown in the table above.
Which city has stricter fines for illegal short-term rentals?
Boston: $300/day for unregistered listing. Chicago: $1,500–$5,000 per offense; each day is a separate offense.