Top 10 Chicago Zillow Investment Listings Ranked by Cash-on-Cash Return
Ten Chicago rental listings from Zillow ranked by cash-on-cash return. South and West Side markets, Realy assumptions, and investor diligence notes.
These ten listings were pulled from Chicago Zillow markets (60628, 60636, 60621, 60652, 60615, 60619, 60649) and ranked by cash-on-cash return (CoC) using Realy’s Chrome extension, sorted by highest CoC first.
Every listing on this screen shows positive CoC under lean assumptions. Most are sub-$100K SFRs and condos on the South and West Side. Foreclosures, bank-owned properties, and long DOM listings dominate. Treat headline yields as a screening signal, not proof of rent-ready condition.
This is a screening list, not a buy list.
Calculation Assumptions Used
| Input | Setting |
|---|---|
| Down payment | 20% · Closing 1% · Rate 6.5% · 30Y fixed |
| Property taxes | 2% of sale value |
| Insurance, vacancy, maintenance, HOA | $0 (add your quotes) |
| Rent | Zillow Rent Zestimate |
See cash-on-cash formula and NOI guide.
At-a-Glance Ranking
| # | Address | Price | Beds/Baths | CoC | Cap Rate | Mo. CF | Rent/mo |
|---|---|---|---|---|---|---|---|
| 1 | 433 W 103rd St | $36,900 | 4 / 1 | 320.9% | 73.5% | $2,072 | $2,320 |
| 2 | 11922 S Perry Ave | $57,500 | 4 / 2 | 210.1% | 50.2% | $2,114 | $2,501 |
| 3 | 4300 W Ford City Dr #401A | $54,900 | 2 / 2 | 166.4% | 41.0% | $1,599 | $1,968 |
| 4 | 6953 S Elizabeth St | $70,000 | 5 / 2 | 136.0% | 34.6% | $1,666 | $2,137 |
| 5 | 7144 S May St | $57,500 | 3 / 1 | 133.8% | 34.2% | $1,346 | $1,733 |
| 6 | 4800 S Lake Park Ave APT 2005 | $80,000 | 2 / 1 | 102.7% | 27.6% | $1,437 | $1,975 |
| 7 | 1541 W Marquette Rd | $60,000 | 2 / 1 | 93.3% | 25.7% | $980 | $1,383 |
| 8 | 8136 S Drexel Ave APT 3 | $59,900 | 2 / 1 | 90.1% | 25.0% | $944 | $1,347 |
| 9 | 6935 S Crandon Ave APT 3D | $79,900 | 2 / 2 | 82.0% | 23.3% | $1,146 | $1,683 |
| 10 | 7137 S Winchester Ave | $94,000 | 4 / 2 | 81.2% | 23.1% | $1,336 | $1,968 |
#1: 433 W 103rd St, Chicago IL 60628
Single family · 4 bed / 1 bath · 1,250 sqft · $36,900
| Metric | Value |
|---|---|
| Cash-on-cash | 320.9% |
| Cap rate | 73.5% |
| Monthly cash flow | $2,072 |
| Total cash down | $7,749 |
Why it ranks #1: Sub-$37K basis with $2,320/mo rent. Only $7,749 cash down under the model.
Investor notes: $3,000 price cut (Jun 16). 37 days on market. Tax assessed $55,000 vs. $36,900 list. One-bath layout. Verify condition, title, and actual rent comps in 60628 before underwriting.
#2: 11922 S Perry Ave, Chicago IL 60628
Single family · 4 bed / 2 bath · 1,168 sqft · $57,500
| Metric | Value |
|---|---|
| Cash-on-cash | 210.1% |
| Cap rate | 50.2% |
| Monthly cash flow | $2,114 |
Investor notes: Bank-owned foreclosure. 84 days on Zillow. Tax assessed $86,000. Foreclosure diligence required: occupancy, liens, and rehab scope.
#3: 4300 W Ford City Dr #401A, Chicago IL 60652
Condo · 2 bed / 2 bath · 900 sqft · $54,900
| Metric | Value |
|---|---|
| Cash-on-cash | 166.4% |
| Cap rate | 41.0% |
| Monthly cash flow | $1,599 |
Investor notes: Re-activated listing. 155 days on market. Prior $4,100 price reduction. Confirm HOA fees (modeled at $0) and rental rules.
#4: 6953 S Elizabeth St, Chicago IL 60636
Single family · 5 bed / 2 bath · 960 sqft · $70,000
| Metric | Value |
|---|---|
| Cash-on-cash | 136.0% |
| Cap rate | 34.6% |
| Monthly cash flow | $1,666 |
Investor notes: 90 days on market. Five bedrooms in under 1,000 sqft. Verify room count and layout match listing before assuming rent.
#5: 7144 S May St, Chicago IL 60621
Single family · 3 bed / 1 bath · 880 sqft · $57,500
| Metric | Value |
|---|---|
| Cash-on-cash | 133.8% |
| Cap rate | 34.2% |
| Monthly cash flow | $1,346 |
Investor notes: Bank-owned foreclosure. 449 days on Zillow. Extreme DOM suggests condition or title issues. Deep diligence required.
#6: 4800 S Lake Park Ave APT 2005, Chicago IL 60615
Condo · 2 bed / 1 bath · 1,500 sqft · $80,000
| Metric | Value |
|---|---|
| Cash-on-cash | 102.7% |
| Cap rate | 27.6% |
| Monthly cash flow | $1,437 |
Investor notes: Hyde Park / Kenwood adjacent 60615. Larger 1,500 sqft unit. 13 days on market. Confirm HOA and building rental policy.
#7: 1541 W Marquette Rd, Chicago IL 60636
Single family · 2 bed / 1 bath · 1,032 sqft · $60,000
| Metric | Value |
|---|---|
| Cash-on-cash | 93.3% |
| Cap rate | 25.7% |
| Monthly cash flow | $980 |
Investor notes: Re-activated listing. 4 days on Zillow. Fresh activity after prior market time.
#8: 8136 S Drexel Ave APT 3, Chicago IL 60619
Condo · 2 bed / 1 bath · 975 sqft · $59,900
| Metric | Value |
|---|---|
| Cash-on-cash | 90.1% |
| Cap rate | 25.0% |
| Monthly cash flow | $944 |
Investor notes: $10,000 price cut (May 14). 62 days on market. Chatham area. Verify condo HOA.
#9: 6935 S Crandon Ave APT 3D, Chicago IL 60649
Condo · 2 bed / 2 bath · 1,400 sqft · $79,900
| Metric | Value |
|---|---|
| Cash-on-cash | 82.0% |
| Cap rate | 23.3% |
| Monthly cash flow | $1,146 |
Investor notes: Brand-new listing. Open house Sat 11am–1pm. Zestimate ~$101K vs. $80K list. Note listing shows a recent price increase.
#10: 7137 S Winchester Ave, Chicago IL 60636
Single family · 4 bed / 2 bath · 2,000 sqft · $94,000
| Metric | Value |
|---|---|
| Cash-on-cash | 81.2% |
| Cap rate | 23.1% |
| Monthly cash flow | $1,336 |
Investor notes: $10,000 price cut (Jul 15). 4 days on market. Tax assessed only $6,613 vs. $94K list. Confirm actual tax bill and property condition on 2,000 sqft footprint.
Chicago Patterns
| Pattern | Takeaway |
|---|---|
| Sub-$100K dominance | All ten listings under $95K with strong Rent Zestimates |
| Foreclosure mix | #2 and #5 are bank-owned. Extra title and condition diligence |
| Condo HOA gap | #3, #6, #8, #9 need real HOA quotes before trusting CoC |
| vs. Philadelphia | Compare Philadelphia top 10 for another sub-$100K cash-flow screen |
Screen Chicago in Realy
- Install Realy
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- Sort by cash-on-cash in the analyzer
Related: First rental checklist · Philadelphia top 10
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