Chicago's two-flats and three-flats are some of the best value-add rentals in the Midwest, but many need a gut rehab before a bank will lend. A bridge loan buys and fixes the building, and a DSCR refinance holds it for the long term.
In short: Our top pick for bridge loans in Chicago is LendingStreet. We fund 1-8 unit investor purchases and rehabs from $150,000 to $5M+, with rates from 7.99%, closings in as little as 10 days and up to 100% of rehab on some programs. Once the units are leased, we refinance into a 30-year DSCR loan on the building's rent. In Chicago, budget taxes on the post-rehab value, register vacant buildings and make sure every unit you count is legal.
For Chicago investors, LendingStreet is our top pick for residential bridge financing. We lend on 1-8 unit investment property from $150,000 to $5M+, with rates from 7.99% and closings in as little as 10 days. Loans are short-term and interest-only, some programs fund up to 90% of cost and up to 100% of the rehab, and there is no appraisal on some bridge programs. Larger balances usually need a full valuation.
When the flats are leased, we can refinance you into a 30-year DSCR loan that qualifies on the building's rent, so you never have to go back to a bank with your tax returns. Get a quote with the form below or call (877) 298-1001.
Well-known bridge lenders include CoreVest, Dominion Financial, Lima One and Roc Capital. Compared scenario by scenario for investors in Chicago, IL, LendingStreet comes out as the stronger choice, and one application covers it.
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 |
|---|---|---|
| Bridge loan above $3M | LendingStreet | Our bridge program runs from $150,000 to $5M+. CoreVest states single-asset bridge loans from $75K to $2M+, and Roc Capital states stabilized bridge loans up to $3,000,000. |
| 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. |
| 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. |
Most Chicago investors weigh a neighborhood bank, a local hard money lender or a private individual. In general terms, here is how those options compare with LendingStreet for a bridge loan.
| What investors need | LendingStreet | Typical community bank | Typical hard money or private lender |
|---|---|---|---|
| Closing speed | As little as 10 days | Often several weeks | Often fast |
| Rehab funding | Up to 100% of rehab on some programs | Often limited on vacant buildings | Varies |
| Leverage on cost | Up to 90% on some programs | Often lower | Varies |
| Exit to a 30-year loan | In-house DSCR refinance on rent | Usually needs tax returns | Not offered |
| Loan size | $150,000 to $5M+ | Relationship based | Limited by available funds |
| Borrow in an LLC | Standard | Sometimes | Usually |
Chicago's small multifamily stock is what makes it a bridge market. Brick two-flats and three-flats, greystones and frame workers' cottages line the bungalow belt and older neighborhoods: Logan Square, Avondale, Hermosa, Belmont Cragin, Portage Park and Albany Park on the Northwest Side, Pilsen, McKinley Park, Bridgeport and Brighton Park to the southwest, and Bronzeville, Woodlawn, Chatham and South Shore on the South Side.
Investors also buy in Berwyn, Cicero, Oak Park, Evanston, Forest Park, Aurora, Elgin and Joliet. Common bridge jobs include gut rehabs of vacant flats, de-conversions of three-flats into a two-unit layout, and garden units that need permits and egress work before they count as legal. Courtyard buildings and anything with 9+ units are commercial; see /commercial.html.
Illinois foreclosures go through the courts, and the judicial sale is not final until the court confirms it. Buyers usually need funds quickly after the sale, so a bridge loan works best when your file is approved before you bid, or on REO and short sales with a normal closing period.
Chicago requires owners of vacant buildings to register them with the city and keep them secured and insured, and the city can fine owners who do not. Budget for the registration and for insurance written on a vacant building until the units are leased. If a private loan or bank balloon on a building you own is coming due, a bridge can pay it off while you finish units or lease up.
Cook County reassesses property in three-year cycles by region, and taxes are paid a year in arrears in two installments. That is why a Chicago closing usually includes a credit from the seller for unpaid taxes. It also means the bill you see may lag the current value by a year or more, and an owner's homeowner or senior exemptions come off when an investor buys. Budget taxes on the value the building will have after the rehab.
The city and the state both charge a transfer tax on a purchase, and part of the city's tax is customarily paid by the buyer. Leases in the city are governed by the Chicago Residential Landlord and Tenant Ordinance, which sets rules on deposits and notices. Winter also matters: exterior masonry, roofing and concrete work slow down in the cold, so build that into your timeline. Confirm local tax and permit details before you buy.
This example is illustrative and not a quote. An investor buys a dated brick two-flat in Portage Park for $400,000 and plans $90,000 of work: two kitchens and baths, a new boiler and masonry repair. The bridge loan covers 80% of the price and all of the rehab, $410,000, about 84% of cost. The estimated interest-only payment is about $3,588 a month once fully drawn, roughly $21,525 over a six-month hold.
After the work, the units lease for $2,200 and $2,100 and the building appraises at $575,000. A 75% LTV cash-out DSCR refinance of $431,250 pays off the bridge loan and returns about $21,250 before closing costs. Estimated principal and interest is about $2,869. Taxes are budgeted at $863 a month on the expected post-rehab value, not the seller's last bill, and insurance at $210. The payment comes to about $3,942, for a DSCR of about 1.09x.
| Item | Amount |
|---|---|
| Purchase price | $400,000 |
| Rehab budget | $90,000 |
| Total project cost | $490,000 |
| Bridge loan (80% of price plus 100% of rehab) | $410,000 |
| Loan-to-cost | About 84% |
| Estimated monthly interest-only payment, fully drawn | $3,588 |
| 6 months of interest-only payments | $21,525 |
| After-repair value | $575,000 |
| DSCR refinance loan | $431,250 |
| Refinance LTV | About 75% |
| Estimated principal and interest | $2,869 |
| Property taxes | $863 |
| Insurance | $210 |
| Total monthly payment | $3,942 |
| Monthly rent | $4,300 |
| DSCR | About 1.09x |
The DSCR refinance qualifies on the combined rent of the units with a 1.0x standard minimum, cash-out up to 75% LTV and 30-year terms. Rent from a garden unit only counts if the unit is legal, so finish permits before you refinance. Seasoning for using the new value varies by program.
Short-term rentals are a weak exit plan in the city. Chicago requires registration and licensing, bans them in some buildings and lets voters restrict new ones precinct by precinct. Plan on 12-month leases, which is how most two-flats and three-flats are rented anyway.
Get every lender's answers to these questions in writing:
Our top pick is LendingStreet, with bridge loans from $150,000 to $5M+, rates from 7.99%, closings in as little as 10 days, rehab funding on some programs and an in-house refinance into a 30-year DSCR loan.
Yes. We finance non-owner-occupied 1-8 unit investment property across Chicago and Cook County and the collar counties, and in all 50 states and DC.
Yes. Vacant buildings are a common bridge use. Register the building with the city as required and carry vacant-building insurance until it is leased.
Cook County taxes are paid a year in arrears, so the seller credits the buyer for taxes owed for the time they owned the property.
Only if it is a legal unit. Get permits and any required egress work done before you refinance.
Sometimes, if your file is approved in advance and the sale terms allow time to close. The court must confirm the sale, so expect some waiting.
Usually not. City licensing rules, building bans and restricted precincts make it unreliable. Plan the exit on long-term leases.
In as little as 10 days when title, insurance and entity documents are ready.
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.