Short-term rental insurance in Chicago, IL

Put a Chicago home on Airbnb or VRBO and a standard homeowners policy backs out as soon as guests start paying to stay. Short-term rental insurance covers the property, your liability for a guest injury, and the income lost while a covered event keeps the rental empty.

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Loved by short-term rental owners across Chicago.

Eric Martin

I had a quote within half an hour and then connected them with my mortgage lender for closing via email. Very easy to work with.

Elizabeth Oreo

They respond quickly and communicate well. I was able to get the policy I needed to convert my vacation home to Airbnb.

Arnold Chambers

The process of getting a landlord policy was very smooth. A few text messages, and the price was great, new policy saved us over $600!

Protect your Chicago short-term rental with the right insurance

The Windy City’s rental market is one of the strongest in the Midwest, with high demand for apartments and short-term rentals alike. Chicago landlords face unique challenges, from strict tenant protection laws to unpredictable weather risks.

Steadily’s short-term rental insurance helps rental property owners, Airbnbs and otherwise, protect their property from liability, guest damage, and lost income while staying compliant with local regulations.

For Chicago hosts who count on steady booking income, a Steadily policy covers the guest-facing risks a homeowners or landlord policy leaves out.

Who is short-term rental insurance for?

Short-term rental insurance protects your investments when they are rented as a vacation rental, Airbnb, VRBO, etc. Short-term rental insurance covers rental periods as short as one night. This insurance offers coverages for:

Legal liabilities

Fire and water damage

Financial protection against natural disasters

Protection for your furnishings

What does short-term rental insurance cover?

We cover a wide range of risks, or you can choose a limited set of coverages for a lower premium

Fire

Fire insurance for rental properties covers structural fire and smoke damage, your personal property, and lost rent while repairs are underway. See what’s covered, exclusions, and how much coverage you need.

Legal liability

Landlord liability insurance pays medical bills, legal defense, and settlements when a tenant or visitor is injured at your rental. Steadily writes $300K to $2M of liability into every landlord policy in all 50 states. Quote in two minutes.

Water

Water damage insurance for rental properties covers burst pipes, roof leaks, appliance overflows, and sewer backups with an endorsement, plus lost rent. See what’s covered, the exclusions, and how much you need.

Storm and hail

Storm and hail damage insurance for landlords covers roof punctures, siding, windows, and wind damage to your rental. See what’s covered, deductibles, and how much coverage you need.

Loss of rent

Loss of rent insurance, also called fair rental value coverage, replaces the rental income you lose when a covered event makes your rental uninhabitable.

Vandalism & burglary

Covers damage made to your rental property by a burglar or a vandal, such as broken windows or defacements made to walls or exterior structures.

Riot & civil commotion

Covers damage to your rental property caused by riots, civil unrest, and public disturbances.

Short-term vs. long-term rentals explained

Short-term rentals

Stays that are 30 days or less at a time.

Rented in short stays

Guests book by the night or week, cycling through constantly instead of one household staying put. A short-term rental policy is priced for that turnover.

Furnished space for paying guests

You supply the beds, furniture, and everything guests use.

Rental income rises and falls with bookings

Revenue is variable and business-like, and loss of rent coverage can replace bookings lost after a covered event.

Requires an STR policy or endorsement

An STR carries a meaningfully different risk profile than a long-term rental. Having the wrong policy can result in coverage gaps and claims being denied.

Long-term rentals

A tenant's permanent residence.

Leased for months or years

One tenant signs a lease and lives there full-time; there's no nightly turnover.

A different risk profile

A single long-term tenant creates far less turnover and guest liability than a stream of nightly visitors, so it's underwritten differently.

Steady rent, tied to a lease

Using a homeowners policy for a rental property can create major coverage gaps.

Does not require an STR policy or endorsement

A tenant-occupied rental calls for a landlord policy built around long-term tenants.

Not sure if your STR is covered? Enter your address and get a free quote instantly:

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Chicago's $1 million coverage requirement

Chicago's ordinance requires at least $1,000,000 in commercial general liability insurance covering the shared-housing activity, though a platform can satisfy it on your behalf. A standard Illinois homeowners policy generally won't reach that limit, and it typically excludes the commercial use of renting to guests to begin with.

Relying only on platform coverage leaves the familiar gaps: nothing between bookings, limited protection for your own property, and no coverage on a direct booking. A dedicated short-term rental policy carries the million-dollar limit the city requires and covers the dwelling, your contents, and the income you lose when a covered event takes the unit offline.

Between the high taxes and the strict registration, a coverage gap is the last complication a Chicago host needs. Run a quick quote to see what short-term rental insurance costs for your Chicago property.

The short-term rental laws Chicago hosts need to follow

Chicago runs short-term rentals through its Shared Housing Ordinance, and registration is step one: a one-time $125 fee, after which your unit has to appear on the city's registrant list before any platform can legally book it. Run more than one unit and you also need a separate operator license.

The catch that surprises hosts is the building-level control. The city keeps a public Prohibited Buildings List, and any unit in a listed building is banned outright, no matter how compliant you are. Owners, associations, and neighbors can add buildings to it, and per-building caps limit how many units in one property can be rentals. Whole zones can be petitioned into short-term-rental bans, too.

Chicago's taxes are among the steepest anywhere. The city stacks a hotel tax and a shared-housing surcharge, part of which funds domestic-violence services, and a 2025 state change pushed the combined load higher still. Operating unregistered starts around $1,500 per violation, and egregious cases run $5,000 to $10,000.