Chicago's signature large rental is the greystone two-flat or three-flat on a North Side side street, and in Lincoln Park, Lakeview or Bucktown many trade well above $1 million. A large-balance DSCR loan qualifies them on their combined rents, not your income.
In short: Yes. LendingStreet finances Chicago-area rentals from $500K to well over $1M with DSCR loans that qualify on the property's rent, with no W-2s or tax returns. Loans start at $150,000 with no stated maximum, rates start at 6.125% for well-qualified borrowers, and purchases go up to 80% LTV, often less on large balances. In Chicago, Cook County property taxes are usually the biggest swing in the ratio, and they can change at each reassessment. Condos add building review and Chicago's short-term rental rules limit nightly income, so confirm the details locally.
Two-flats and three-flats, often with a limestone greystone front, were built across the North and Northwest Sides a century ago. Each floor is its own apartment, and many have a garden unit below. For a DSCR loan, two or three leases spread the payment far better than one condo at the same price.
Lakefront and downtown condos are the other big group, in the Gold Coast, Streeterville, River North, the West Loop and the South Loop. In the suburbs, large-balance rentals are mostly single-family homes on the North Shore and in Oak Park and Hinsdale.
Each type brings different questions, so it helps to know which one you are buying before you run the numbers.
These are general patterns. Rents and values vary block by block, so use recent leases and sales nearby.
Cook County reassesses property on a three-year cycle, rotating between the city, the northern suburbs and the southern suburbs. A reassessment can raise or lower the bill, sometimes sharply, and the change goes straight into the DSCR payment.
Owner-occupants receive a homeowner exemption that investors do not. If the seller lived in one unit of the flat, your bill may be higher after the exemption comes off. Property owners can appeal assessments with the Assessor and the Board of Review, and many investors do so regularly.
When you run the ratio, use the current bill without the homeowner exemption and ask when the area is next due for reassessment. A file that only clears 1.0x on today's tax bill leaves little room.
This example is illustrative and not a quote. An investor buys a greystone three-flat in Lakeview for $1,500,000. The units rent for $3,700, $3,500 and $3,300, for $10,500 a month in total. Taxes, without the homeowner exemption, are budgeted at $2,100 a month and insurance at $350.
At 70% LTV the loan is $1,050,000 and the down payment is $450,000. At a sample rate of 7.25% on a 30-year fixed, principal and interest is about $7,163. The total payment is about $9,613, and DSCR is $10,500 divided by $9,613, or about 1.09x.
If a reassessment pushed taxes to $2,600 a month, the payment would be about $10,113 and DSCR about 1.04x. It still clears the 1.0x standard minimum, but with less room, which is why the tax bill deserves as much attention as the rate.
| Line item | Current taxes | After a reassessment |
|---|---|---|
| Total rent (three units) | $10,500 | $10,500 |
| Principal and interest ($1,050,000 at 7.25%, 30 years) | $7,163 | $7,163 |
| Property taxes | $2,100 | $2,600 |
| Insurance | $350 | $350 |
| Total monthly payment | $9,613 | $10,113 |
| DSCR | About 1.09x | About 1.04x |
Many flats have a garden or basement apartment. If that unit is not part of the legal unit count, most programs will not give it rent credit, and an appraiser may note it as a zoning issue. Chicago has expanded the rules for coach houses and basement units in parts of the city, so check the zoning and permit history for the address.
Century-old masonry buildings raise practical questions: roof and parapet condition, boilers or older heating systems, and rear wooden porches, which inspectors and insurers look at closely. Get an insurance quote during attorney review so there are no surprises late in the process.
If the building needs real work before it can rent at market, a short-term bridge loan first and a DSCR refinance after is a common path.
Many older Chicago flats run on a single boiler, and the owner pays for heat. Others have separate furnaces and meters so each tenant pays their own gas and electric. The DSCR formula only counts principal, interest, taxes, insurance and any association dues, so utilities do not change the ratio directly.
They do change what you keep. A three-flat with owner-paid heat can look strong on the DSCR worksheet and still leave thin cash flow after a cold January. Ask the seller for 12 months of utility bills, and factor them into your own budget.
Separately metered buildings can be easier to price for insurance and simpler to manage. Converting a building to separate systems is a capital project, so if you plan one, a bridge loan first and a DSCR refinance after may fit better than starting with a long-term loan.
Chicago's Residential Landlord and Tenant Ordinance covers most rentals in the city and sets strict rules on security deposits, interest and notices. Owner-occupied buildings with six or fewer units are exempt, but investor-owned flats generally are not. Review deposit records when you buy an occupied building.
Condos go through project review: budget, reserves, insurance, litigation and rental rules. Many Chicago associations cap the number of units that can be leased or set minimum lease terms. Monthly assessments count in the payment, and in full-service lakefront towers they can be large.
Chicago requires registration for shared housing and vacation rentals, and buildings can join a list that prohibits them. Most large Chicago DSCR loans qualify on annual leases. Confirm current rules with the city and the association.
A large share of Chicago investor loans fall between $500K and $1M. Common examples are two-flats in Logan Square, Avondale, Irving Park and Portage Park, three-flats in Pilsen and Bridgeport, condos in the South Loop, River North and Lakeview, and single-family rentals in Oak Park, Forest Park and Evanston.
On these balances, leverage often sits closer to the program maximums of 80% LTV on purchases and 75% on cash-out, and reserves are often lighter than on $1M+ loans. Both vary by program, and the 1.0x standard minimum DSCR and 620 credit floor stay the same.
Cook County taxes and the legal unit count still decide many files at this size. Pull the actual tax bill and confirm the units before you sign.
The program basics hold above $1M: qualify on the property, no W-2s or tax returns, a 620 minimum credit score, LLC borrowers allowed and 30-year fixed options. Larger balances are priced case by case, maximum LTV is often lower and reserve requirements are often higher.
Some programs require a second appraisal or a more detailed review. Buildings with five or more units move to our multifamily programs, underwritten on net operating income. Owners of five or more Chicago rentals can ask about a blanket portfolio loan with one closing and portfolio pricing.
| Item | Greystone two- or three-flat | Lakefront condo | North Shore single-family |
|---|---|---|---|
| Rent streams | Two or three | One | One |
| Monthly assessment | Usually none | Yes, counted in the payment | Rare |
| Main review item | Legal unit count and condition | Building budget and rental cap | Tax bill and rent support |
| Ratio at the same price | Often strongest | Often weakest | Middle |
Chicago contracts commonly include an attorney review period, and attorneys handle most closings. Share your contract dates with the financing team up front.
Send the address, price, rents and target leverage. The financing team reviews the scenario and comes back with 2-3 options.
Yes. DSCR loans start at $150,000 with no stated maximum. Loans of $500K to $1M are common for two-flats in Logan Square and Irving Park, South Loop and Lakeview condos, and single-family rentals in Oak Park and Evanston.
Yes. A three-flat is a three-unit residential property, a core DSCR property type. The loan qualifies on the combined rent of all three units.
Only if it is part of the legal unit count. Unpermitted units usually get no rent credit. Check zoning and permit records before you sign.
The homeowner exemption ends when an investor buys, and reassessments can raise the bill. Underwrite with a bill that excludes the exemption.
It covers most Chicago rentals. Owner-occupied buildings with six or fewer units are exempt, but investor-owned buildings generally are not. Confirm with a Chicago attorney.
Often not. The city requires registration, many associations ban short stays and buildings can join a prohibited list. Plan on annual leases unless the rules clearly allow it.
Our DSCR programs have no stated maximum. Larger balances are reviewed and priced case by case, often with lower maximum LTV and higher reserves.
Yes. Cash-out goes up to 75% LTV, often lower on large balances. The combined rents must cover the new payment at the program minimum, and seasoning varies by program.
Not with our programs. LendingStreet finances non-owner-occupied investment property only.
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