Chicago gives flippers a deep supply of brick bungalows, two-flats and greystones, plus a city permit process and layered transfer taxes that reward planning. The lender you pick should fund the rehab in draws, close quickly and offer a rental exit if the two-flat makes more sense to keep.
In short: Our top pick for fix and flip loans in Chicago, IL is LendingStreet. It funds up to 90% of cost and up to 100% of rehab on some programs, closes in as little as 10 days, and offers a DSCR rental refinance if you keep the home. It lends across the city and the suburbs, from Bungalow Belt rehabs to North Side gut renovations above $1M.
LendingStreet is a business-purpose lender built for real estate investors, and fix and flip loans are one of our core programs. For Chicagoland projects, we fund up to 90% of cost and up to 100% of the rehab on some programs, from $150,000 to $5M+, and we can close in as little as 10 days.
It fits investors buying 1 to 8 unit homes to renovate and resell, or to renovate and keep as a rental. When the project is done, you can sell, or refinance into a 30-year DSCR rental loan with the same team. To start, get a quote with the form below or call (877) 298-1001.
If you are weighing Dominion Financial, LendingOne, Lima One and RCN Capital for a fix and flip 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. |
| 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. |
Most Chicago flippers have tried a bank, a local hard money lender or a private individual at some time. All of them can close deals, but they differ on leverage, speed and what happens after the rehab. The table sets LendingStreet next to the typical options.
Private individual lenders can be flexible, but terms vary from person to person and there is rarely a long-term loan at the end.
| What flippers need | LendingStreet | Typical local bank | Typical local hard money lender |
|---|---|---|---|
| Leverage on the project | Up to 90% of cost on some programs | Often lower; more cash in | Varies by lender |
| Rehab funding | Up to 100% of rehab on some programs, in draws | Often limited for flips | Often offered; terms vary |
| Closing speed | As little as 10 days | Often several weeks | Often fast |
| Loan size | $150,000 to $5M+ | Varies; may limit investor loans | Varies; large loans can be harder |
| Entity borrowers | LLCs welcome | Varies | Usually allowed |
| Long-term rental option | DSCR refinance with the same team | Possible; often based on tax returns | Usually short-term only |
| Where they lend | All 50 states and DC | Often a local footprint | Often local or regional |
On the Northwest and Southwest Sides, investors buy bungalows and two-flats in Portage Park, Irving Park, Jefferson Park, Belmont Cragin, Bridgeport, McKinley Park, Brighton Park and Garfield Ridge. Logan Square and Avondale are higher-priced, and Lincoln Park and Lakeview gut rehabs can pass $1M, which our program covers.
In the suburbs, Berwyn, Cicero, Oak Lawn, Elmhurst, Evanston, Aurora, Elgin and Joliet each have their own mix of older brick homes and postwar ranches. On the South Side, Beverly, Mount Greenwood and Chatham have solid brick housing stock at a range of prices.
Most of the city's flip stock is brick from the 1900s to the 1950s: bungalows, two-flats, greystones and frame cottages with basements. Water in basements, old sewer lines, tired boilers and lead water service lines come up often. Converting a two-flat back to a single-family home is a common high-end plan, but it changes the zoning and the buyer pool, so check first.
In the city, permits run through the Department of Buildings, and work under a permit generally needs a licensed general contractor. Suburbs run their own building departments, and some require a city inspection before a sale. Chicago rentals also fall under the city's landlord and tenant ordinance if you keep the property.
Illinois and Cook County both charge transfer taxes on sales, and Chicago adds its own city transfer tax on top, with portions paid by buyer and seller. Suburbs may add a local transfer tax. Attorneys commonly handle Illinois closings, so budget their fees on both ends.
Cook County assesses residential property at a 10% assessment ratio and reassesses on a three-year cycle by region. Use the full tax bill without any homeowner exemptions when you budget. Confirm current transfer tax and tax figures locally.
This example is illustrative and not a quote. An investor buys a dated brick bungalow in Portage Park for $340,000 with a $110,000 rehab budget, for a total project cost of $450,000. At 90% of cost, the loan is $405,000. The full $110,000 rehab budget is held for draws, and $295,000 goes toward the purchase at closing.
The investor brings $45,000 toward the project, plus about $8,000 in estimated buy-side closing costs and $7,500 for taxes, insurance and utilities over a 6-month hold, so about $60,500 in all. The finished home sells for $585,000, with about $37,000 in selling costs.
Before loan interest, the profit is about $82,500 ($585,000 minus $37,000, $450,000, $8,000 and $7,500). The interest-only payments come out of that figure, and your quote will show them. If the sale market softens, the same home can be refinanced into a DSCR rental loan instead.
| Line item | Amount |
|---|---|
| Purchase price | $340,000 |
| Rehab budget (funded in draws) | $110,000 |
| Total project cost | $450,000 |
| Loan at 90% of cost | $405,000 |
| Investor cash toward project | $45,000 |
| Estimated closing and holding costs | $15,500 |
| Sale price less selling costs | $548,000 |
| Profit before loan interest | $82,500 |
Updated bungalows in neighborhoods with good transit and schools tend to sell well in spring and early summer, and winter listings often sit longer. Permit timing is the biggest schedule risk, so get plans and permits moving before you close when you can.
If you decide to hold, a DSCR rental loan qualifies on the property's rent with no W-2s or tax returns, a 620 minimum credit score and a 1.0x standard minimum DSCR, with 30-year terms. Rate-and-term refinances go up to 80% LTV on some programs and cash-out up to 75%; seasoning varies by program. See our bridge to DSCR guide.
Ask every lender the same questions so you can compare offers side by side.
Here is how LendingStreet answers: up to 90% of cost and up to 100% of rehab on some programs; draws after inspections; closings in as little as 10 days; LLC borrowers welcome; loans from $150,000 to $5M+; and a DSCR refinance with a 1.0x standard minimum, with seasoning that varies by program. Ready to compare? Get a quote with the form below or call (877) 298-1001.
Our top pick is LendingStreet. We fund up to 90% of cost and up to 100% of rehab on some programs, close in as little as 10 days, and offer a DSCR rental refinance if you decide to keep the home. Get a quote with the form below or call (877) 298-1001.
Yes. LendingStreet lends on 1 to 8 unit investment properties in Chicago, IL and across Illinois, and in all 50 states and DC.
Loans run from $150,000 to $5M+. On some programs we fund up to 90% of total cost and up to 100% of the rehab budget. Final leverage depends on the property, the plan and your experience.
In as little as 10 days. Having the purchase contract, rehab budget, scope of work and entity documents ready helps keep the timeline short.
Yes. LLC and other entity borrowers are welcome, and you will usually sign for the loan personally as well.
You can refinance into a DSCR rental loan qualified on the property's rent, with 30-year terms and a 1.0x standard minimum DSCR. Seasoning varies by program, so ask early.
Run both. A deconversion to a single-family home can sell for more in some neighborhoods, but it changes the buyer pool. Keeping it as a two-flat lets you refinance into a DSCR loan qualified on the combined rent. LendingStreet can quote both paths.
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