Before you read the numbers: these estimates assume every home is rent-ready. ApriFind doesn't have condition data yet, so repairs needed to reach these rents are not included, and the cheapest homes are the most likely to need them. Property tax uses Chicago's 2025 effective rate for rental (investor-owned) property (1.44%), from the Lincoln Institute. See What these numbers assume.
Chicago is the largest city in our top 10 for cash flow, and the reason is its two- and three-flats: small multi-family buildings that make up a fifth of its listings. In our ranking of the 50 largest US metros, it had the tenth-highest share of listings with positive cash flow. We ran every active for-sale listing in the city through ApriFind on October 9, 2026 and analyzed 3,695 properties, each with a rent estimate built from nearby comparable rentals.
Key takeaways
- 22% of listings show positive cash flow with 20% down at a 7% mortgage rate. The median listing is negative (−$788 per month), with a 3.7% median cap rate.
- The South and West Sides lead: in 60621, 60623, 60624, 60636, and 60619, 58–73% of listings cash-flow on paper, at median prices of $249,993–$399,000.
- Small multi-family is the standout property type: 61% of 2–4 unit buildings cash-flow under our standard assumptions, with a 7.4% median cap rate. They're also the most sensitive to costs those assumptions may understate: with heavier costs, 36% do.
- Price is the dividing line. 81% of listings under $100,000 cash-flow on paper, against 22% at $200,000–$300,000. Those cheapest homes are also the most likely to need significant repairs.
- Cash flow isn't limited to the weakest areas. 20% of listings in neighborhoods with an Apri Score of 4–7 cash-flow, and 23% of all cash-flowing listings are in areas scoring 1–5.
Returns by ZIP code
ZIP codes with at least 40 analyzed listings, ranked by the share with positive cash flow.
| ZIP | Listings | Median price | Median est. rent | Median cap rate | Median monthly cash flow | Listings that cash-flow |
|---|---|---|---|---|---|---|
| 60621 | 59 | $249,993 | $3,348 | 9.8% | $709 | 73% |
| 60623 | 71 | $399,000 | $4,618 | 7.6% | $460 | 65% |
| 60624 | 51 | $375,000 | $3,900 | 7.8% | $362 | 65% |
| 60636 | 54 | $274,500 | $2,150 | 7.9% | $231 | 61% |
| 60619 | 128 | $277,450 | $2,500 | 7.2% | $179 | 58% |
| 60628 | 143 | $199,900 | $2,000 | 7.8% | $188 | 57% |
| 60644 | 43 | $389,000 | $3,372 | 6.5% | $47 | 54% |
| 60617 | 126 | $259,900 | $2,150 | 6.6% | $34 | 51% |
| 60612 | 51 | $584,900 | $4,100 | 6.3% | −$73 | 47% |
| 60609 | 59 | $335,000 | $3,266 | 5.5% | −$218 | 42% |
| 60620 | 118 | $293,750 | $2,400 | 5.3% | −$259 | 39% |
| 60649 | 96 | $167,450 | $1,773 | 5.0% | −$188 | 38% |
| 60651 | 55 | $400,000 | $2,968 | 5.1% | −$420 | 33% |
| 60643 | 67 | $294,995 | $2,050 | 5.0% | −$282 | 31% |
| 60608 | 62 | $483,950 | $3,412 | 4.7% | −$471 | 27% |
| 60629 | 53 | $359,900 | $1,958 | 4.1% | −$636 | 26% |
| 60637 | 103 | $369,000 | $2,500 | 4.3% | −$621 | 26% |
| 60639 | 40 | $482,000 | $3,488 | 4.3% | −$628 | 25% |
| 60616 | 83 | $390,000 | $3,311 | 4.1% | −$703 | 24% |
| 60632 | 58 | $397,000 | $1,939 | 3.9% | −$740 | 21% |
| 60641 | 64 | $571,500 | $3,520 | 3.6% | −$1,027 | 16% |
| 60625 | 47 | $364,900 | $2,299 | 3.7% | −$775 | 15% |
| 60622 | 72 | $825,000 | $4,727 | 3.0% | −$1,775 | 14% |
| 60618 | 75 | $825,000 | $4,735 | 2.9% | −$2,042 | 13% |
| 60647 | 86 | $845,000 | $3,592 | 2.9% | −$1,843 | 12% |
| 60645 | 49 | $299,999 | $2,447 | 3.7% | −$693 | 10% |
| 60642 | 41 | $774,000 | $4,968 | 3.9% | −$1,621 | 10% |
| 60653 | 53 | $479,000 | $2,700 | 3.1% | −$1,386 | 9% |
| 60607 | 86 | $567,500 | $4,010 | 2.3% | −$1,577 | 9% |
| 60605 | 71 | $369,000 | $3,500 | 3.7% | −$784 | 8% |
| 60652 | 40 | $355,000 | $1,800 | 2.7% | −$1,068 | 8% |
| 60615 | 96 | $319,250 | $2,237 | 1.9% | −$1,116 | 7% |
| 60630 | 54 | $499,950 | $2,795 | 3.8% | −$1,044 | 6% |
| 60660 | 56 | $273,950 | $2,225 | 2.1% | −$898 | 5% |
| 60640 | 68 | $332,450 | $2,422 | 2.8% | −$1,179 | 4% |
| 60610 | 99 | $486,000 | $4,500 | 3.0% | −$1,436 | 4% |
| 60634 | 71 | $499,900 | $2,500 | 2.9% | −$1,270 | 3% |
| 60611 | 305 | $599,000 | $4,009 | 1.6% | −$2,430 | 2% |
| 60657 | 78 | $599,900 | $3,495 | 2.0% | −$2,225 | 1% |
| 60613 | 86 | $308,950 | $2,495 | 1.9% | −$1,146 | 1% |
| 60654 | 87 | $455,000 | $4,004 | 3.0% | −$1,121 | 1% |
| 60614 | 102 | $797,950 | $3,922 | 1.9% | −$2,770 | 0% |
| 60601 | 60 | $985,000 | $4,644 | 1.0% | −$4,483 | 0% |
Downtown and the North Side lakefront (60601, 60611, 60614, 60654, 60657) rarely cash-flow, and 60611 alone has more listings than any other ZIP, mostly condos.
Returns by property type and price
| Property type | Listings | Median price | Median est. rent | Median cap rate | Listings that cash-flow |
|---|---|---|---|---|---|
| Condo | 1,713 | $398,000 | $2,995 | 2.9% | 7% |
| Single family | 1,162 | $349,950 | $2,243 | 3.7% | 18% |
| Multi-family (whole building) | 718 | $480,000 | $5,329 | 7.4% | 61% |
| Townhouse | 102 | $469,500 | $3,240 | 4.4% | 37% |
| Price range | Listings | Median est. rent | Median cap rate | Listings that cash-flow |
|---|---|---|---|---|
| Under $100,000 | 69 | $1,625 | 13.4% | 81% |
| $100,000–$200,000 | 391 | $1,874 | 7.3% | 57% |
| $200,000–$300,000 | 722 | $2,222 | 4.8% | 22% |
| $300,000 and up | 2,513 | $3,650 | 3.0% | 14% |
How to sense-check multi-family. A typical Chicago multi-family listing is a three-flat built around 1910, with 6 bedrooms in total, listed at about $480,000. Its estimated rent, about $5,330 a month for the building, compares with a $2,598 median asking rent for a two-bedroom apartment in Chicago. The cost side is less certain. Our standard assumptions don't include owner-paid utilities, and in older small multi-family buildings the owner often pays water and sewer. Older buildings also tend to cost more to insure and maintain. With $150 a month of owner-paid utilities, insurance at 1% of the price instead of 0.5%, 10% vacancy, and 15% maintenance, the share of multi-family listings that cash-flow falls from 61% to 36%.
Returns by Apri Score (neighborhood rating)
The Apri Score is ApriFind's proprietary 1-to-10 neighborhood rating, built from census-level socioeconomic data including income, education, employment, and housing quality. It compares each neighborhood with others in the same state: 1 is among the strongest, 10 among the weakest. ApriFind shows it on every listing and as a map layer. It's built to show, before you make an offer, whether a high return comes with a weaker location. See the Apri Score for every listing in any city.
| Apri Score | Share of listings | Median price | Median est. rent | Median cap rate | Median monthly cash flow | Listings that cash-flow |
|---|---|---|---|---|---|---|
| 1–3 (strongest) | 47% | $534,900 | $3,496 | 2.7% | −$1,474 | 6% |
| 4–7 | 28% | $395,000 | $2,500 | 3.8% | −$748 | 20% |
| 8–10 (weakest) | 25% | $290,000 | $2,240 | 6.3% | −$18 | 50% |
Based on the 3,383 listings with an Apri Score.
Chicago's cash flow isn't confined to its weakest neighborhoods. 20% of listings in Apri Score 4–7 areas cash-flow on paper, at a median price of $395,000 and a 3.8% cap rate, and 23% of all cash-flowing listings are in areas scoring 1–5. That makes Chicago one of the more balanced markets in our data for investors who want cash flow without buying in the weakest areas: 193 listings in Apri Score 4–7 areas showed positive cash flow.
The weakest areas still lead on paper (50%), and they can also bring more turnover, longer vacancies, more collection problems, and older housing than the same 5% vacancy assumption reflects.
Chicago asking rents by bedrooms
Median asking rent for single-family and townhouse rentals on the market:
| Bedrooms | Median asking rent | Rentals |
|---|---|---|
| 1 | $1,850 | 131 |
| 2 | $2,000 | 362 |
| 3 | $2,400 | 282 |
| 4 | $2,795 | 65 |
| 5+ | $3,400 | 30 |
What these numbers assume
1. Every home is rent-ready. Rent estimates come from comparable rentals currently on the market, which are homes in rentable condition. ApriFind doesn't have condition data yet. A home that needs a roof, a furnace, or a full renovation won't earn these rents until the work is done, and the cost of that work is not included in these returns. This matters most for the cheapest listings: the 81% cash-flow rate under $100,000 describes those homes after they're rent-ready. Budget for an inspection and repairs before relying on any of these numbers.
2. Property tax uses Chicago's rate for rental property. We use 1.44%, the Lincoln Institute's 2025 effective tax rate for rental (investor-owned) property in Chicago (source). Your parcel's actual bill can differ. If taxes were half a point higher, 19% of listings would still cash-flow; a full point higher, 16%.
3. Rent estimates are estimates. Rent estimates are based on asking rents from comparable rental listings nearby, which can run above what tenants ultimately sign for. Check them against local leasing evidence before relying on them.
4. Financing and expenses. 20% down, 7.0% 30-year fixed mortgage, 5% vacancy, 10% property management, 10% maintenance reserve, insurance, and HOA dues where listed.
5. Some listings are excluded. We left out 195 listings priced far below comparable homes nearby, or whose estimated rent was far above what similar listings nearby earn (often shells, auction starting bids, or restricted units), along with vacant land. This "Verify condition" flag is a rough filter: it can't detect a property's actual condition, so homes needing major work remain in these figures.
Methodology
All active for-sale listings with a Chicago, IL address on October 9, 2026, analyzed with ApriFind. Each property's rent comes from ApriFind's proprietary rent model, which considers comparable rentals nearby and how closely they match on factors including location, property type, size, bedrooms, bathrooms, and age. Multi-family rent is the estimated rent for the whole building. Cap rate is net operating income divided by price; cash flow is rent minus all costs including the mortgage.
Listings change daily. Search Chicago on ApriFind to see today's listings with your own down payment, rate, tax rate, and expense assumptions.
FAQ
Is Chicago a good place to buy a rental property in 2026? In our October 2026 analysis, 22% of active Chicago listings showed positive cash flow at 20% down and 7% interest, the tenth-highest share among the main cities of the 50 largest US metros. Those numbers assume rent-ready homes, and many of the cheapest listings need repairs, so inspection and renovation costs decide whether a specific property works.
What is the property tax rate on a Chicago rental property? The Lincoln Institute's 2025 study puts Chicago's effective tax rate on rental (investor-owned) property at 1.44% of market value. A specific parcel's bill can differ.
What is the average cap rate in Chicago? The median cap rate across 3,695 active listings was 3.7%, from about 9.8% in 60621 to 1.0% in 60601.
Can you find cash flow in better Chicago neighborhoods? More than in most top cash-flow markets in our data. In our October 2026 analysis, 20% of listings in areas with an Apri Score of 4–7 (ApriFind's 1-to-10 neighborhood rating, where 10 is weakest) showed positive cash flow, and 23% of all cash-flowing listings were in areas scoring 1–5.
Which Chicago ZIP codes have the best rental returns? 60621, 60623, and 60624 had the highest share of listings with positive cash flow (65–73%), with median prices between $249,993 and $399,000.
ApriFind provides informational tools only and does not provide investment, financial, legal, or tax advice. Figures are estimates from listing data on one date; actual results vary.