Chicago vs Kansas City
Illinois Legal but Limited | Missouri Legal with Permit
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | Kansas City, Missouri |
|---|---|---|
| Legality Status | Legal but Limited | Legal with Permit |
| Permit Fee | $250 annual registration fee | $250/year permit fee |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | 7.5% Transient Guest Tax + sales tax |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Annual |
| Platform Remits Taxes | Yes | No — host must remit |
| Max Fine Example | $1,500–$5,000 per offense; each day is a separate offense | $500/offense for operating without permit |
| Verdict | Kansas City 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
Kansas City, Missouri
Status Legal with Permit
Permit Fee $250/year permit fee
Tax Rate 7.5% Transient Guest Tax + sales tax
Day Limit No limit
Renewal Annual
Platform Tax No
Max Fine $500/offense for operating without permit
Kansas City 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 →Kansas City Overview
Short-term rental permits required for all listings. Both owner-occupied and investor-owned properties are eligible. Must maintain guest registry and provide local emergency contact within 30 minutes.
Full Kansas City guide →Frequently Asked Questions
Is it easier to Airbnb in Chicago or Kansas City?
Chicago is classified as "Legal but Limited" while Kansas City is "Legal with Permit." Chicago's permit fee is $250 annual registration fee compared to $250/year permit fee in Kansas City.
Which city has higher STR taxes — Chicago or Kansas City?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while Kansas City charges 7.5% Transient Guest Tax + 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. Kansas City: $500/offense for operating without permit.