Key Takeaways
- Stable Market with Strategic Timing: Chicago’s median home price held steady at $350,000 with 0% year-over-year change as of October 2025, while active listings dropped 9.92% annually and 37.41% over three years, creating reduced competition among flippers in a stable third-most populous U.S. city.
- High Property Tax Impact on Holding Costs: Cook County’s 1.98% effective annual property tax rate ranks among the nation’s highest, requiring flippers to carefully account for elevated holding costs during renovations to protect profit margins.
- 70% Rule and High-ROI Renovations: Investors should pay no more than 70% of after-repair value minus renovation costs, while prioritizing improvements with highest return on investment (ROI) including garage door replacements (282.2% ROI), entry door replacements (235% ROI), and manufactured stone veneer (190.6% ROI).
- Multiple Exit Strategy Options: Over half of Chicago homes are renter-occupied with $1,380 median gross rent, allowing flippers to pivot to rental strategies using DSCR loans if resale markets shift unfavorably.
As a home flipper, now may be a good time to buy property in Chicago. The Chicago real estate forecast suggests favorable conditions, with home values holding steady from a year ago and positioned to resume their long-term upward trend.
At ABL, we’ve financed fix-and-flip projects in Chicago and across Illinois for years. Our fast, flexible loan programs let you secure deals fast while not having to worry about funding during construction. No matter your experience level, we’re here to help make your next flip a success.
Chicago Housing Market Snapshot
In October 2025, the median home price in Chicago was $350,000. That’s a 0% change from a year earlier and up 9.17% from three years ago. The Chicago real estate forecast indicates potential for home values to revert back to their long-term upward trend, offering flippers significant equity gains.
Meanwhile, there were 8,560 active property listings in Chicago in October 2025. That’s 9.92% fewer than a year earlier and 37.41% fewer than three years earlier. In other words, the supply of homes for sale is shrinking, which increases competition among buyers (all else equal).
It’s also important to note that U.S. mortgage rates gradually fell in 2025, with the average 30-year fixed rate at 6.18% as of December 24, 2025. Lower mortgage rates raise buyers’ purchasing power, making properties more accessible to flippers (and end-buyers).
Opportunities for Chicago Home Flippers
Now that you’ve had a glimpse of Chicago’s housing trends, let’s dive into their implications for flippers, starting with the opportunities:
Low-Risk Entry
As the third-most populous U.S. city, Chicago has a stable real estate market, with a constant demand for housing. This, coupled with buyers’ shrinking selection of homes, makes Chicago relatively low risk. If you buy a house here, you can be relatively certain you can resell it.
Multiple Exit Strategies
Even if you don’t resell a property, you can always list it as a rental. Over half of Chicago homes are occupied by renters, and the median gross rent is $1,380. Already plan to rent out a property after renovations? ABL has you covered with long-term DSCR loans.
Compete Against Fewer Flippers
Fewer homes on the market often means fewer active flippers to compete against. As a result, you may have more negotiation power with sellers when buying. For expert advice on potential property deals, contact one of our local Chicago team members.
The Challenges of Flipping Properties in Chicago
Next, let’s take a look at the potential challenges of flipping Chicago homes:
Finding Properties to Buy
With fewer homes on the market, finding property to buy can be challenging. So get creative. For example, look for vacant homes, those with deferred maintenance, homeowners who are behind on their taxes or mortgage payments, and other signs of distress.
High Property Taxes
Cook County, Illinois, has an effective annual property tax rate of 1.98%—one of the highest in the nation. For flippers, this means higher holding costs while you get your property ready to list. If you’re not careful, this could eat into your profit margins and even lead to a loss.
Harsh Winters
Chicago is known for its harsh winters. As a result, you must plan renovations around the weather. Otherwise, you could end up with unexpected delays and cost overruns.
Chicago Neighborhoods by Median Home Price
Of course, your Chicago home flipping prospects can vary by neighborhood. Here are some of the top neighborhoods to consider by lowest to highest median home price:
| Neighborhood | Median home price | Listing $ / sq ft | Median monthly Rental Price |
| Far Southeast Side | $215,000 | $144 | $1,550 /mo |
| Southwest Side | $265,000 | $184 | $1,537 /mo |
| South Side | $270,000 | $159 | $1,750 /mo |
| Far Southwest Side | $279,000 | $174 | $1,600 /mo |
| Far North Side | $369,900 | $250 | $1,715 /mo |
| River North | $425,000 | $417 | $3,066 /mo |
| West Side | $429,900 | $322 | $2,573 /mo |
| Near West Side | $435,000 | $352 | $2,838 /mo |
| The Loop | $444,945 | $401 | $2,774 /mo |
| Northwest Side | $459,999 | $248 | $1,800 /mo |
| Downtown Chicago | $465,000 | $399 | $2,887 /mo |
| Near North Side | $499,999 | $418 | $2,949 /mo |
| Lake View | $519,500 | $341 | $1,980 /mo |
| North Side | $650,000 | $369 | $2,095 /mo |
| West Town | $675,000 | $359 | $2,598 /mo |
3 Tips for Flipping Real Estate in Chicago
No matter where you choose to flip property in Chicago, follow these best practices:
Follow the 70% Rule
The 70% rule says you should pay no more than 70% of a property’s after-repair value (ARV) minus renovation costs. For example, if after $50,000 in repairs a property’s expected ARV is $300,000, you should pay no more than $175,000 for it ([$300,000 – $50,000] x 0.7).
This helps ensure there’s enough profit leftover to make the flip worthwhile.
Prioritize Renovations with the Highest ROI
To maximize your returns, focus on renovations with the highest ROI potential. According to the 2025 Cost vs. Value Report for the East North Central region, renovations with the highest ROI include garage door replacements (282.2%), entry door replacement (235%), and manufactured stone veneer (190.6%).
Build a Reliable Team
The best home flippers don’t work alone. They work with other experts. Build a reliable team of contractors, real estate agents, and lenders like ABL to help you execute successful flips.
Fund Your Next Chicago Flip With an ABL Loan
Seize your next Chicago fix-and-flip opportunity by getting financing from ABL. We offer fast fix-and-flip loans that can be tailored to your specific needs. All it takes is sharing a little about you and the project, and we’ll close on the loan in 30 days or less. Pre-qualify today!