Sell Your Chicago Rental Property with Tenants in Place — We Handle Everything
Tired of being a Chicago landlord? Sell your rental property with tenants in place. No evictions, no lease terminations, no property management headaches before you close.
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Being a Chicago landlord is increasingly complex. Rising property taxes, the city's strong tenant protections under the Residential Landlord and Tenant Ordinance, maintenance costs for aging building stock, and the emotional toll of managing difficult tenant relationships — many Chicago landlords are ready to exit the rental business. The challenge: selling a tenant-occupied property on the traditional market is difficult because most retail buyers want vacant possession. We buy tenant-occupied Chicago rental properties exactly as they are, tenants and all.
What You Get When You Sell to Sam
Chicago's Landlord-Tenant Laws and Why They Complicate Sales
Chicago has one of the strongest tenant protection frameworks in the Midwest under the Residential Landlord and Tenant Ordinance (RLTO). Tenants with active leases have the right to remain in the property through their lease term regardless of a change in ownership. Month-to-month tenants are entitled to a minimum of 30 days' written notice before being required to vacate, and Chicago's Just Cause for Eviction ordinance provides additional protections in covered properties.
This means that if you want to sell a tenant-occupied Chicago property to a retail buyer expecting vacant possession, you must either wait for leases to expire naturally, negotiate voluntary move-outs (typically involving cash-for-keys payments of several thousand dollars per tenant), or pursue a formal Cook County eviction — a process that takes 3 to 12 months depending on the situation, and which may trigger additional tenant protections.
Cash investors who understand Chicago's landlord-tenant framework — including us — buy tenant-occupied properties regularly. When you sell to us, we take over the landlord-tenant relationship at closing. We become the new landlord, inherit the leases, collect the security deposits, and manage the tenant transition. You walk away clean from all landlord obligations.
Types of Chicago Rental Properties We Buy
We buy all types of Chicago rental properties with tenants in place: single-family homes rented to one household, two-flats and three-flats with long-term tenants in each unit, courtyard apartment buildings, and larger multi-unit properties throughout Chicago and the suburbs. We are also comfortable with mixed-occupancy situations — for example, a three-flat where one unit is occupied on a lease, one unit is vacant, and one unit has a month-to-month tenant.
We also buy properties with difficult tenant situations. Tenants who are significantly behind on rent, month-to-month holdovers who have stopped responding to notices, or buildings with ongoing disputes — you do not need to resolve any of these issues before we close. We take the property in its current landlord-tenant condition and manage the resolution ourselves after closing.
For multi-unit properties, we review the existing leases, current rental amounts, and security deposit information as part of our due diligence — but these are informational inputs to our valuation, not conditions of sale. We buy regardless of what we find in the rent rolls, adjusting our offer accordingly.
Your Legal Obligations at Closing
When you sell a Chicago rental property, you have legal obligations to tenants that transfer to the buyer at closing. Under Chicago's RLTO, security deposits — including any accumulated interest required by ordinance — must be transferred to the new owner at closing. Existing leases transfer with the property. And tenants must receive written notice of the change in ownership within a specific timeframe.
We handle all of this documentation as part of the standard closing process. We coordinate with your attorney and the title company to ensure the security deposit transfer is properly executed and all required tenant notifications are prepared and sent. You fulfill your legal obligations through the standard closing process — no extra administrative burden on your part. When you hand us the keys, your landlord obligations end.
How It Works
Call or Submit Your Info
Reach out by phone or fill out our form. We ask a few quick questions about the property.
We Assess the Property
We schedule a brief walkthrough — usually within 24 hours. No cleaning or repairs needed.
Receive a Cash Offer
We present a written, no-obligation cash offer within 24 hours of seeing the property.
Close on Your Timeline
You choose the closing date. We can close in as few as 7 days or give you more time if needed.
Frequently Asked Questions
Do tenants need to leave before you buy my Chicago rental?
No. We buy Chicago rental properties with tenants in place. The landlord-tenant relationship transfers to us at closing — we become the new landlord, and you are no longer responsible for any tenant obligations, maintenance requests, or lease management.
What happens to the tenant security deposits at closing?
Security deposits — including any interest accumulated under Chicago's RLTO — are transferred to us at closing. This is handled through the title company as part of the standard closing process and documented properly. You are released from all security deposit obligations at the time of transfer.
Can you buy my Chicago rental if tenants are behind on rent?
Yes. Rent arrears, ongoing tenant disputes, and problem tenant situations are things we deal with regularly as a cash buyer. These issues factor into our property assessment and offer price, but they do not prevent us from purchasing.
How do I know the tenants' rights will be protected during the sale?
All existing leases transfer to us at closing, and tenants remain in their units under the same lease terms. We provide proper written notification of the ownership change as required by Chicago's RLTO. We take tenant obligations seriously and ensure every transition is handled legally and professionally.