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.
| Requirement | Chicago, Illinois | New York City, New York |
|---|---|---|
| Legality Status | Legal but Limited | Effectively Banned |
| Permit Fee | $250 annual registration fee | $145 registration fee (OSE) |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | 5.875% hotel room occupancy tax + state/city sales tax |
| Annual Day Limit | No limit | No limit |
| 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 | $5,000 first offense; up to $7,500 for subsequent violations |
| Verdict | Chicago has more favorable STR regulations overall. | |
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.
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 →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.
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.
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. 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. New York City: $5,000 first offense; up to $7,500 for subsequent violations.