Chicago vs Milwaukee
Illinois Legal but Limited | Wisconsin Legal with Permit
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Chicago, Illinois | Milwaukee, Wisconsin |
|---|---|---|
| Legality Status | Legal but Limited | Legal with Permit |
| Permit Fee | $250 annual registration fee | $110 annual license + $300 one-time pre-inspection fee |
| Tax Rate | 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County | 5% state sales + 3% county room tax + 7% city room tax (15% combined) |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Annual |
| Platform Remits Taxes | Yes | Yes |
| Max Fine Example | $1,500–$5,000 per offense; each day is a separate offense | $150–$500 first offense; steeper fines and permit revocation for repeat offenses |
| Verdict | Milwaukee 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
Milwaukee, Wisconsin
Status Legal with Permit
Permit Fee $110 annual license + $300 one-time pre-inspection fee
Tax Rate 5% state sales + 3% county room tax + 7% city room tax (15% combined)
Day Limit No limit
Renewal Annual
Platform Tax Yes
Max Fine $150–$500 first offense; steeper fines and permit revocation for repeat offenses
Milwaukee 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 →Milwaukee Overview
Tourist Rooming House license required for rentals under one month. Properties must pass safety inspection for building code and fire safety compliance before license is issued.
Full Milwaukee guide →Frequently Asked Questions
Is it easier to Airbnb in Chicago or Milwaukee?
Chicago is classified as "Legal but Limited" while Milwaukee is "Legal with Permit." Chicago's permit fee is $250 annual registration fee compared to $110 annual license + $300 one-time pre-inspection fee in Milwaukee.
Which city has higher STR taxes — Chicago or Milwaukee?
Chicago charges 10.5% combined city tax (4.5% Hotel Accommodations + 6% Shared Housing Surcharge) + 1% Cook County, while Milwaukee charges 5% state sales + 3% county room tax + 7% city room tax (15% combined). 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. Milwaukee: $150–$500 first offense; steeper fines and permit revocation for repeat offenses.