Chicago's brick two-flats and bungalows are built to last, but decades of deferred maintenance make many of them perfect rehab projects for investors.
In short: Our top pick for hard money style financing in Chicago is LendingStreet. We close in as little as 10 days, fund up to 90% of cost and up to 100% of rehab on some programs, and finance 1-8 unit buildings, including two-flats and three-flats. When the work is done, we can refinance the building into a DSCR rental loan that qualifies on combined rent.
LendingStreet is an investor lender with fix and flip, bridge and DSCR rental loans in one place. Every loan is a business-purpose loan on non-owner-occupied property. In Chicago that means short-term, interest-only financing on 1-8 unit properties from $150,000 to $5M+, with up to 90% of cost and up to 100% of rehab on some programs.
It fits investors renovating two-flats and three-flats on the Northwest and Southwest Sides, brick bungalows, greystones and small 5-8 unit courtyard buildings. Chicago is one of the best small multi-family markets in the country for a buy, renovate and hold plan, which makes an in-house DSCR exit especially useful.
The next step is simple: get a quote with the form below, or call (877) 298-1001 and talk through the deal.
If you are weighing CoreVest, Dominion Financial, LendingOne, Lima One and RCN Capital for a hard money loan for investors in Chicago, IL, this is the short version: LendingStreet wins the scenarios below, and you can get a quote with the form below.
Figures for other lenders are as stated on each lender's own website as of November 2026. Lender terms change, so verify current terms with any lender before you apply. Ready to see your numbers? Use the form below or call (877) 298-1001.
| Scenario | Best fit | Why |
|---|---|---|
| Fix and flip above $3M | LendingStreet | Our fix and flip program runs from $150,000 to $5M+. LendingOne states fix and flip loans up to $3,000,000, and RCN Capital states up to $2M. |
| Bridge close in about 10 days | LendingStreet | We can close in as little as 10 days. CoreVest states its bridge loans typically close within 2 to 4 weeks. |
| Flip of a 5-8 unit building | LendingStreet | We finance 1-8 unit investor properties. RCN Capital states its fix and flip loans cover 1-4 family homes, condos and townhomes. |
| Property in any state, including DC | LendingStreet | We lend in all 50 states and DC. Lima One states it lends across 46 states, and Dominion Financial lists 49 states plus DC. |
Chicago investors weigh LendingStreet against local hard money lenders, private money and neighborhood banks. This is a general comparison; individual lenders differ.
| What investors need | LendingStreet | Typical local hard money lender | Private individual lender | Local bank or credit union |
|---|---|---|---|---|
| Close quickly | As little as 10 days | Often fast; varies by lender | Can be fast; depends on the person | Usually slower; full underwriting |
| Leverage | Up to 90% of cost | Varies; often lower | Negotiated deal by deal | Often a larger down payment |
| Rehab money | Up to 100% of rehab on some programs, in draws | Varies | Varies | Often limited on distressed property |
| Long-term rental loan | DSCR refinance in-house | Usually short-term only | Rarely | Possible; often needs tax returns |
| Loan size | $150,000 to $5M+ | Varies | Limited by one person's capital | Varies by bank |
| Two-flats and 5-8 unit buildings | Financed as residential, 1-8 units | Varies | Varies | Often prefers stabilized buildings |
On the Northwest Side, Portage Park, Belmont Cragin, Avondale, Hermosa and Albany Park have brick two-flats and bungalows that suit both flips and rentals. On the Southwest Side, Brighton Park, Gage Park, Archer Heights and McKinley Park offer lower entry prices. South Side neighborhoods such as Chatham, Auburn Gresham and South Shore draw value-add investors, while Bridgeport and Pilsen attract buyers looking for older frame and brick homes.
Close-in suburbs like Berwyn, Cicero, Oak Lawn and Evergreen Park have similar housing stock and their own permit offices.
Some investors try to add a garden unit or attic unit to a two-flat. That can lift rent and resale value, but only where zoning and the building code allow it, so confirm the legal path with the city before you put it in the budget. Renovated units with in-unit laundry, updated kitchens and central air tend to lease fastest.
Cook County taxes residential property on an assessment ratio of 10% of market value, then applies local rates that are high compared with much of the country. Reassessments rotate by area. Budget taxes carefully, especially if you plan to hold.
Illinois and Cook County charge transfer taxes, usually paid by the seller, and the City of Chicago adds its own transfer tax, usually paid by the buyer. Illinois is a judicial foreclosure state. Confirm current rates and practices with a local attorney, since Chicago closings commonly involve attorneys on both sides.
Chicago's Department of Buildings issues permits, and scope matters: larger renovations can need architect drawings and a standard plan review, which takes longer than an express permit. Porches, masonry, electrical and plumbing work all draw inspector attention in older buildings.
Winter slows exterior work, and many two-flats need masonry repair, porch rebuilds or roof work. Schedule those for warmer months and keep interiors moving through the winter.
This example is illustrative and not a quote. An investor buys a brick two-flat in Portage Park for $390,000 and budgets $120,000 to renovate both units, a total cost of $510,000. At 90% of cost, the loan is $459,000. The investor brings $51,000 plus about $11,000 in closing costs, or $62,000 in all.
The estimated interest-only payment is about $4,016 a month on the full balance. Over 6 months that is about $24,098, plus about $5,400 in taxes and insurance, for an all-in cost of about $550,498. At a $640,000 resale with about $41,600 in selling costs, the estimated profit is about $47,902 before income taxes.
Holding works here. A DSCR refinance at 75% of $640,000 is $480,000, which pays off the flip loan with about $21,000 left before closing costs. Estimated principal and interest is about $3,274; with $780 in taxes and $230 in insurance, the payment is about $4,284. At $4,700 in combined rent, DSCR is about 1.10x.
| Line item | Amount |
|---|---|
| Purchase plus rehab | $510,000 |
| Loan at 90% of cost | $459,000 |
| Cash to close incl. closing costs | $62,000 |
| Estimated interest-only payment | $4,016 a month |
| All-in cost | $550,498 |
| Selling costs | $41,600 |
| Estimated profit before income taxes | $47,902 |
Ask every lender the same questions, in writing, before you sign a purchase contract.
Here is how LendingStreet answers them: up to 90% of cost and up to 100% of rehab on some programs; a 1.0x standard DSCR minimum on the rental exit, with sub-1.0 programs available; seasoning that varies by program; LLC borrowers as standard; closings in as little as 10 days; and loans from $150,000 to $5M+, with larger balances reviewed case by case.
Chicago rents on renovated two-flats and three-flats often support a 30-year DSCR loan that qualifies on combined rent, with no W-2s or tax returns. That makes buy, renovate, rent and refinance a natural plan. Seasoning varies by program, so ask before you close the flip loan.
Get a quote with the form below or call (877) 298-1001 to price a Chicago building.
Our top pick is LendingStreet. You get hard money style speed with closings in as little as 10 days, up to 90% of cost and up to 100% of rehab on some programs, and an in-house DSCR loan for two-flats and other rentals you keep.
Yes. We lend across Chicago, Cook County and Illinois, and in all 50 states and DC.
Yes. Two- to four-unit buildings are a core property type, and 5-8 unit buildings are also financed as residential.
Residential property is assessed at 10% of market value, then local rates apply. Bills can be high, so budget them carefully in your hold numbers.
By custom, the buyer usually pays the city portion and the seller pays the state and county portions. Confirm with your attorney.
It depends on scope. Simple work can move quickly, while larger renovations needing plan review take longer. Build that into your timeline.
Rates start from 7.99%. Pricing depends on leverage, the property and your experience.
2-3 competing quotes from 30+ capital sources. No credit pull. No commitment.
By clicking, you provide express written consent to be contacted by LendingStreet (NMLS #1734316) via SMS, phone, or email, possibly using automated technology, regarding your loan inquiry. Reply STOP to opt out. Consent is not required to obtain services. See our Privacy Policy and Terms.