Baltimore vs Chicago

Maryland Legal but Limited | Illinois Legal but Limited

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

Baltimore, Maryland
Status Legal but Limited
Permit Fee $200 biennial license fee per dwelling unit
Tax Rate 9.5% Baltimore Hotel Tax + 6% state lodging tax
Day Limit No limit
Renewal Biennial
Platform Tax Yes
Max Fine $500/violation for unlicensed operation; up to $1,000 for state registration violations
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

Baltimore charges $200 biennial license fee per dwelling unit for STR licensing, while Chicago charges $250 annual registration fee. Baltimore renewal is biennial, and Chicago renewal is annual. Both cities share a similar regulatory stance, classified as "Legal but Limited."

Tax Obligations

In Baltimore, hosts pay 9.5% Baltimore Hotel Tax + 6% state lodging 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 Baltimore face penalties including $500/violation for unlicensed operation; up to $1,000 for state registration violations. 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.

Baltimore Overview

Primary residence required; max two licenses per host. Stays must be under 90 consecutive nights. Must pass home inspection.

Contact: Baltimore DHCD Property Registration — (410) 396-3575

Full Baltimore 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 Baltimore or Chicago?
Baltimore is classified as "Legal but Limited" while Chicago is "Legal but Limited." Baltimore's permit fee is $200 biennial license fee per dwelling unit compared to $250 annual registration fee in Chicago. Both cities have comparable regulatory frameworks.
Which city has higher STR taxes — Baltimore or Chicago?
Baltimore charges 9.5% Baltimore Hotel Tax + 6% state lodging 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?
Baltimore: $500/violation for unlicensed operation; up to $1,000 for state registration violations. 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 Baltimore and Chicago have day limits for Airbnb?
Baltimore has no annual day limit. Chicago has no annual day limit.
Which city is better for first-time Airbnb hosts — Baltimore or Chicago?
For new hosts, consider the total cost of entry: Baltimore charges $200 biennial license fee per dwelling unit for permits with 9.5% Baltimore Hotel Tax + 6% state lodging 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 Baltimore and Chicago makes compliance easier for beginners.