Investment properties in Chicago

Every live listing in Chicago we can model, ranked — with the price, the return and the risks worked out on each one. Filter it below.

Median gross yield: 8.3%
Median asking price: $399,000
Listings with a yield: 9,359

Market figures as of 2026-09-15

↓ PRICE CUT ×1 −2%RENT: WELL EVIDENCED (23 COMPS)

Strong

$87,900 · $80/sqft

9.9%net

2 bed condo IL 60637, 60637

Solid 17.2% return before costs

2 bed1 bath1,100 sqft

Monthly profit

+$385

Cash needed

$24K

Return after costs

9.9%

RENT: WELL EVIDENCED (20 COMPS)

Strong

$120,000 · $60/sqft

9.9%net

3 bed single-family home IL 60633, 60633

Solid 19.2% return before costs

3 bed2 bath2,000 sqft

Monthly profit

+$683

Cash needed

$33K

Return after costs

9.9%

4950 S Chicago Beach Dr #4A, Chicago, IL 60615

Priced below market −14%RENT: WELL EVIDENCED (10 COMPS)

Strong

$250,000 · $60/sqft

9.8%net

4 bed condo IL 60615, 60615

Solid 17.2% return before costs

4 bed4 bath4,197 sqft

Monthly profit

+$1,092

Cash needed

$69K

Return after costs

9.8%

20 E Goethe St APT 206, Chicago, IL 60610

RENT: WELL EVIDENCED (47 COMPS)

Strong

$185,000

9.7%net

1 bed condo IL 60610, 60610

Solid 17.3% return before costs

1 bed1 bath

Monthly profit

+$821

Cash needed

$51K

Return after costs

9.7%

431 S Dearborn St APT 1204, Chicago, IL 60605

RENT: WELL EVIDENCED (23 COMPS)

Strong

$384,900 · $214/sqft

9.6%net

3 bed condo IL 60605, 60605

Solid 17.8% return before costs

3 bed2 bath1,800 sqft

Monthly profit

+$1,848

Cash needed

$107K

Return after costs

9.6%

5300 S Shore Dr APT 59, Chicago, IL 60615

RENT: WELL EVIDENCED (22 COMPS)

Strong

$139,999 · $92/sqft

9.6%net

2 bed condo IL 60615, 60615

Solid 17.9% return before costs

2 bed2 bath1,516 sqft

Monthly profit

+$676

Cash needed

$39K

Return after costs

9.6%

RENT: EVIDENCED (19 COMPS)

Strong

$130,000 · $104/sqft

10.0%net

4 bed single-family home IL 60620, 60620

Solid 20.6% return before costs

4 bed2 bath1,246 sqft

Monthly profit

+$866

Cash needed

$36K

Return after costs

10.0%

2921 S Michigan Ave APT 109, Chicago, IL 60616

RENT: WELL EVIDENCED (16 COMPS)

Strong

$118,500 · $158/sqft

9.5%net

1 bed condo IL 60616, 60616

Solid 21.3% return before costs

1 bed1 bath750 sqft

Monthly profit

+$842

Cash needed

$33K

Return after costs

9.5%

RENT: WELL EVIDENCED (15 COMPS)

Strong

$139,000 · $125/sqft

9.3%net

3 bed single-family home IL 60628, 60628

Solid 16.3% return before costs

3 bed2 bath1,114 sqft

Monthly profit

+$526

Cash needed

$39K

Return after costs

9.3%

RENT: EVIDENCED (58 COMPS)

Solid

$110,000 · $50/sqft

9.8%net

3 bed condo IL 60649, 60649

Solid 19.0% return before costs

3 bed3 bath2,200 sqft

Monthly profit

+$616

Cash needed

$31K

Return after costs

9.8%

RENT: WELL EVIDENCED (17 COMPS)

Solid

$184,900 · $80/sqft

9.2%net

4 bed single-family home IL 60643, 60643

Solid 18.9% return before costs

4 bed3 bath2,300 sqft

Monthly profit

+$1,018

Cash needed

$51K

Return after costs

9.2%

10741 S Pulaski Rd APT 2C, Chicago, IL 60655

RENT: WELL EVIDENCED (35 COMPS)

Solid

$124,900 · $121/sqft

9.0%net

2 bed condo IL 60655, 60655

Solid 15.4% return before costs

2 bed1 bath1,032 sqft

Monthly profit

+$391

Cash needed

$35K

Return after costs

9.0%

RENT: EVIDENCED (8 COMPS)

Solid

$150,000 · $153/sqft

9.4%net

4 bed single-family home IL 60632, 60632

Solid 16.1% return before costs

4 bed2 bath980 sqft

Monthly profit

+$544

Cash needed

$42K

Return after costs

9.4%

RENT: WELL EVIDENCED (60 COMPS)

Solid

$119,000 · $107/sqft

8.9%net

3 bed single-family home IL 60636, 60636

Solid 16.1% return before costs

3 bed2 bath1,108 sqft

Monthly profit

+$434

Cash needed

$33K

Return after costs

8.9%

Priced below market −6%RENT: EVIDENCED (62 COMPS)

Solid

$114,900 · $61/sqft

9.3%net

3 bed condo IL 60649, 60649

Solid 17.9% return before costs

3 bed2 bath1,878 sqft

Monthly profit

+$553

Cash needed

$32K

Return after costs

9.3%

RENT: EVIDENCED (78 COMPS)

Solid

$115,000 · $78/sqft

9.3%net

3 bed single-family home IL 60619, 60619

Solid 17.2% return before costs

3 bed2 bath1,475 sqft

Monthly profit

+$503

Cash needed

$32K

Return after costs

9.3%

230 E Ontario St APT 1304, Chicago, IL 60611

RENT: WELL EVIDENCED (106 COMPS)

Solid

$187,900

8.8%net

1 bed condo IL 60611, 60611

Solid 16.6% return before costs

1 bed1 bath

Monthly profit

+$750

Cash needed

$52K

Return after costs

8.8%

RENT: WELL EVIDENCED (17 COMPS)

Solid

$149,900

8.8%net

4 bed multi-family IL 60609, 60609

Solid 15.5% return before costs

4 bed2 bath

Monthly profit

+$485

Cash needed

$42K

Return after costs

8.8%

RENT: WELL EVIDENCED (53 COMPS)

Solid

$119,999 · $130/sqft

8.8%net

3 bed single-family home IL 60636, 60636

Solid 16.0% return before costs

3 bed2 bath924 sqft

Monthly profit

+$427

Cash needed

$33K

Return after costs

8.8%

2511 E 76th St Unit 3, Chicago, IL 60649

RENT: WELL EVIDENCED (53 COMPS)

Solid

$90,000 · $60/sqft

8.7%net

2 bed condo IL 60649, 60649

Solid 16.8% return before costs

2 bed1 bath1,500 sqft

Monthly profit

+$370

Cash needed

$25K

Return after costs

8.7%

(undisclosed Address), Chicago, IL 60628

Priced below market −34%

Solid

$164,900

9.7%net

6 bed multi-family IL 60628, 60628

Solid 15.7% return before costs

6 bed3 bath

Monthly profit

+$551

Cash needed

$46K

Return after costs

9.7%

5000 S East End Ave APT 2A, Chicago, IL 60615

RENT: WELL EVIDENCED (23 COMPS)

Solid

$180,000 · $69/sqft

8.6%net

3 bed condo IL 60615, 60615

Solid 20.3% return before costs

3 bed3 bath2,600 sqft

Monthly profit

+$1,164

Cash needed

$50K

Return after costs

8.6%

RENT: WELL EVIDENCED (21 COMPS)

Solid

$149,900

8.3%net

4 bed multi-family IL 60636, 60636

Solid 16.7% return before costs

4 bed2 bath

Monthly profit

+$604

Cash needed

$42K

Return after costs

8.3%

RENT: EVIDENCED (10 COMPS)

Solid

$149,900

8.8%net

4 bed multi-family IL 60617, 60617

Solid 16.9% return before costs

4 bed2 bath

Monthly profit

+$623

Cash needed

$42K

Return after costs

8.8%

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