Boston vs Chicago

Massachusetts Legal but Limited | Illinois Legal but Limited

Disclaimer: General information only — not legal advice. Verify with your local government.

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.

Permits & Licensing

Boston charges $25 registration fee for STR licensing, while Chicago charges $250 annual registration fee. Boston renewal is annual, and Chicago renewal is annual. Both cities share a similar regulatory stance, classified as "Legal but Limited."

Tax Obligations

In Boston, hosts pay 6.5% state excise + 6% city convention center tax. In Chicago, hosts pay 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County. Both cities benefit from automatic platform tax collection through Airbnb and similar services, simplifying compliance for hosts.

Day Limits & Restrictions

Neither city imposes an annual day limit on short-term rentals, giving hosts year-round flexibility.

Fines & Enforcement

Hosts operating without a permit in Boston face penalties including $300/day for unregistered listing. In Chicago, violations can result in $1,500–$5,000 per offense; each day is a separate offense. Both cities actively enforce their STR regulations, so securing proper licensing before listing is essential in either market.

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.

Contact: Boston Inspectional Services — (617) 635-5300

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.

Contact: Dept. of Business Affairs and Consumer Protection — (312) 744-6060

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. Both cities have comparable regulatory frameworks.
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.
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. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Boston and Chicago have day limits for Airbnb?
Boston has no annual day limit. Chicago has no annual day limit.
Which city is better for first-time Airbnb hosts — Boston or Chicago?
For new hosts, consider the total cost of entry: Boston charges $25 registration fee for permits with 6.5% state excise + 6% city convention center tax in taxes. Chicago charges $250 annual registration fee with 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County. Automatic tax collection in Boston and Chicago makes compliance easier for beginners.