Chicago vs New York City

Illinois Legal but Limited | New York Effectively Banned

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

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
New York City, New York
Status Effectively Banned
Permit Fee $145 registration fee (OSE)
Tax Rate 5.875% hotel room occupancy tax + state/city sales tax
Day Limit No limit
Renewal Every 2 years
Platform Tax Yes
Max Fine $5,000 first offense; up to $7,500 for subsequent violations

Chicago has more favorable STR regulations overall.

Permits & Licensing

Chicago charges $250 annual registration fee for STR licensing, while New York City charges $145 registration fee (OSE). Chicago renewal is annual, and New York City renewal is every 2 years. Overall, Chicago has a more permissive regulatory environment (Legal but Limited) compared to New York City (Effectively Banned).

Tax Obligations

In Chicago, hosts pay 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County. In New York City, hosts pay 5.875% hotel room occupancy tax + state/city sales tax. 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 Chicago face penalties including $1,500–$5,000 per offense; each day is a separate offense. In New York City, violations can result in $5,000 first offense; up to $7,500 for subsequent violations. Both cities actively enforce their STR regulations, so securing proper licensing before listing is essential in either market.

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 →

New York City Overview

Local Law 18 (2023) requires hosts to register with OSE, be present during stays, and limits guests to 2. Entire-apartment rentals under 30 days are effectively banned. Only hosted stays with the owner present are permitted.

Contact: NYC Mayor's Office of Special Enforcement — (212) 676-4101

Full New York City guide →

Frequently Asked Questions

Is it easier to Airbnb in Chicago or New York City?
Chicago is classified as "Legal but Limited" while New York City is "Effectively Banned." Chicago's permit fee is $250 annual registration fee compared to $145 registration fee (OSE) in New York City. Overall, Chicago has a more host-friendly regulatory environment.
Which city has higher STR taxes — Chicago or New York City?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while New York City charges 5.875% hotel room occupancy tax + state/city sales tax.
Which city has stricter fines for illegal short-term rentals?
Chicago: $1,500–$5,000 per offense; each day is a separate offense. New York City: $5,000 first offense; up to $7,500 for subsequent violations. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Chicago and New York City have day limits for Airbnb?
Chicago has no annual day limit. New York City has no annual day limit.
Which city is better for first-time Airbnb hosts — Chicago or New York City?
For new hosts, consider the total cost of entry: Chicago charges $250 annual registration fee for permits with 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County in taxes. New York City charges $145 registration fee (OSE) with 5.875% hotel room occupancy tax + state/city sales tax. Automatic tax collection in Chicago and New York City makes compliance easier for beginners.