Chicago, IL Fourplexes for Sale

Chicago, Illinois, offers a dynamic urban experience with a world-class cultural scene, including renowned museums, theaters, and diverse dining options. The city's iconic architecture and vibrant neighborhoods provide a unique and engaging living environment. Chicago boasts a strong job market with opportunities across various industries, including finance, technology, and healthcare. Its extensive public transportation system and central location make it easy to navigate and explore. Additionally, the city's rich history and diverse community contribute to its energetic and inclusive atmosphere.

Listings: 36
Updated: Jun 21, 2026
Median Price: $525,000
Median Size: 3,421 sqft
Higher-Confidence Cash-Flow Candidates: 0

Cash-flow figures are directional screening signals only. Verify rent, unit mix, taxes, insurance, financing, condition, and listing status independently.

Compare Chicago listings with the national cash-flow rankings

Available Listings

Chicago Duplex, Triplex, and Fourplex Listings

36 results

$550,000

3900 W Jackson Blvd, Chicago, IL, 60624

2-4 Units

Beds: 15
Baths: 6
Size: -- sqft

Est. Rent: $8,850/mo
Est. Cash Flow: +$3,395/mo
Modeled Cost: $5,455/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $2,732/mo

$500,000

3619 W 5th Ave, Chicago, IL, 60624

2-4 Units

Beds: 11
Baths: 5
Size: -- sqft

Est. Rent: $7,480/mo
Est. Cash Flow: +$2,634/mo
Modeled Cost: $4,846/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $2,483/mo

$400,000

3929 W Van Buren St, Chicago, IL, 60624

2-4 Units

Beds: 9
Baths: 4
Size: -- sqft

Est. Rent: $6,600/mo
Est. Cash Flow: +$2,599/mo
Modeled Cost: $4,001/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $1,987/mo

$379,900

2722 W 18th St, Chicago, IL, 60608

2-4 Units

Beds: 8
Baths: 4.5
Size: -- sqft

Est. Rent: $6,000/mo
Est. Cash Flow: +$2,254/mo
Modeled Cost: $3,746/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $1,887/mo

2704 N Central Park Ave, Chicago, IL, 60647

$499,000

2704 N Central Park Ave, Chicago, IL, 60647

2-4 Units

Beds: 6
Baths: 2
Size: -- sqft

Est. Rent: $6,660/mo
Est. Cash Flow: +$1,985/mo
Modeled Cost: $4,675/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $2,478/mo

$320,000

4026 W Monroe St, Chicago, IL, 60624

2-4 Units

Beds: 6
Baths: 2
Size: -- sqft

Est. Rent: $4,620/mo
Est. Cash Flow: +$1,553/mo
Modeled Cost: $3,067/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $1,589/mo

$845,000

3130 W Wilson Ave, Chicago, IL, 60625

2-4 Units

Beds: 8
Baths: 3
Size: -- sqft

Est. Rent: $8,400/mo
Est. Cash Flow: +$1,059/mo
Modeled Cost: $7,341/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $4,197/mo

$319,900

2452 W Marquette Rd, Chicago, IL, 60629

2-4 Units

Beds: 5
Baths: 3
Size: -- sqft

Est. Rent: $3,930/mo
Est. Cash Flow: +$1,001/mo
Modeled Cost: $2,929/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $1,589/mo

Chicago, IL, 60624

$575,000

Chicago, IL, 60624

2-4 Units

Beds: 7
Baths: 3
Size: -- sqft

Est. Rent: $5,990/mo
Est. Cash Flow: +$939/mo
Modeled Cost: $5,051/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $2,856/mo

$749,999

1420 N Austin Blvd, Oak Park, IL, 60302

2-4 Units

Beds: 8
Baths: 4.5
Size: -- sqft

Est. Rent: $7,160/mo
Est. Cash Flow: +$703/mo
Modeled Cost: $6,457/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $3,725/mo

$409,999

Chicago, IL, 60620

2-4 Units

Beds: 5
Baths: 3
Size: -- sqft

Est. Rent: $4,190/mo
Est. Cash Flow: +$605/mo
Modeled Cost: $3,585/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $2,036/mo

7529 N Winchester Ave, Chicago, IL, 60626

$600,000

7529 N Winchester Ave, Chicago, IL, 60626

2-4 Units

Beds: 5
Baths: 3
Size: 2,304 sqft

Est. Rent: $5,780/mo
Est. Cash Flow: +$604/mo
Modeled Cost: $5,176/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $2,980/mo

1630 W Melrose St, Chicago, IL, 60657

$550,000

1630 W Melrose St, Chicago, IL, 60657

2-4 Units

Beds: 4
Baths: 2
Size: -- sqft

Est. Rent: $5,340/mo
Est. Cash Flow: +$587/mo
Modeled Cost: $4,753/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $2,732/mo

$399,900

1528 S Christiana Ave, Chicago, IL, 60623

2-4 Units

Beds: 6
Baths: 2
Size: -- sqft

Est. Rent: $3,960/mo
Est. Cash Flow: +$488/mo
Modeled Cost: $3,472/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $1,986/mo

$659,999

5007 N Lawndale Ave, Chicago, IL, 60625

2-4 Units

Beds: 5
Baths: 3
Size: -- sqft

Est. Rent: $6,060/mo
Est. Cash Flow: +$427/mo
Modeled Cost: $5,633/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $3,278/mo

4507 S Michigan Ave, Chicago, IL, 60653

$650,000

4507 S Michigan Ave, Chicago, IL, 60653

2-4 Units

Beds: 9
Baths: 6
Size: 7,095 sqft

Est. Rent: $5,830/mo
Est. Cash Flow: +$309/mo
Modeled Cost: $5,521/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $3,228/mo

5542 S Paulina St, Chicago, IL, 60636

$275,000

5542 S Paulina St, Chicago, IL, 60636

2-4 Units

Beds: 4
Baths: 2
Size: 2,326 sqft

Est. Rent: $2,640/mo
Est. Cash Flow: +$270/mo
Modeled Cost: $2,370/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $1,366/mo

$499,999

4921 W Superior St, Chicago, IL, 60644

2-4 Units

Beds: 6
Baths: 3
Size: -- sqft

Est. Rent: $4,350/mo
Est. Cash Flow: +$130/mo
Modeled Cost: $4,220/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $2,483/mo

3404 N Tripp Ave, Chicago, IL, 60641

$588,800

3404 N Tripp Ave, Chicago, IL, 60641

2-4 Units

Beds: 5
Baths: 3
Size: -- sqft

Est. Rent: $4,970/mo
Est. Cash Flow: +$30/mo
Modeled Cost: $4,940/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $2,925/mo

8718 S Kingston Ave, Chicago, IL, 60617

$475,000

8718 S Kingston Ave, Chicago, IL, 60617

Duplex

Beds: 7
Baths: 3
Size: -- sqft

Est. Rent: $3,640/mo
Est. Cash Flow: -$271/mo
Modeled Cost: $3,911/mo
Estimate Confidence: Medium
Rent Source: Estimated

Est. P&I: $2,359/mo

1639 N Claremont Ave, Chicago, IL, 60647

$1,310,000

1639 N Claremont Ave, Chicago, IL, 60647

2-4 Units

Beds: 9
Baths: 4
Size: 4,516 sqft

Est. Rent: $9,520/mo
Est. Cash Flow: -$1,162/mo
Modeled Cost: $10,682/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $6,507/mo

1419 W Cullerton St, Chicago, IL, 60608

$849,000

1419 W Cullerton St, Chicago, IL, 60608

Triplex

Beds: 8
Baths: 4
Size: -- sqft

Est. Rent: $5,360/mo
Est. Cash Flow: -$1,401/mo
Modeled Cost: $6,761/mo
Estimate Confidence: Medium
Rent Source: Estimated

Est. P&I: $4,217/mo

1959 W Balmoral Ave, Chicago, IL, 60640

$899,000

1959 W Balmoral Ave, Chicago, IL, 60640

2-4 Units

Beds: 4
Baths: 2
Size: -- sqft

Est. Rent: $4,600/mo
Est. Cash Flow: -$2,343/mo
Modeled Cost: $6,943/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $4,465/mo

$450,000

3535 W Flournoy St, Chicago, IL, 60624

2-4 Units

Beds: 12
Baths: 3
Size: -- sqft

Est. Rent: $7,920/mo
Est. Cash Flow: +$3,321/mo
Modeled Cost: $4,599/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $2,235/mo

$300,000

4300 W Adams St, Chicago, IL, 60624

2-4 Units

Beds: 8
Baths: 3
Size: -- sqft

Est. Rent: $6,160/mo
Est. Cash Flow: +$2,917/mo
Modeled Cost: $3,243/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $1,490/mo

$365,000

Chicago, IL, 60637

2-4 Units

Beds: 9
Baths: 2
Size: -- sqft

Est. Rent: $6,560/mo
Est. Cash Flow: +$2,803/mo
Modeled Cost: $3,757/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $1,813/mo

$350,000

6559 S Eberhart Ave, Chicago, IL, 60637

2-4 Units

Beds: 8
Baths: 2
Size: -- sqft

Est. Rent: $6,120/mo
Est. Cash Flow: +$2,551/mo
Modeled Cost: $3,569/mo
Estimate Confidence: Low
Rent Source: Estimated

Est. P&I: $1,738/mo

4435 S Campbell Ave, Chicago, IL, 60632

$0

4435 S Campbell Ave, Chicago, IL, 60632

Duplex

Beds: 4
Baths: 2.5
Size: -- sqft

Est. Rent: N/A
Est. Cash Flow: N/A
Modeled Cost: N/A
Estimate Confidence: N/A
Rent Source: N/A

Est. P&I: $0/mo

230 W Saint Paul Ave, Chicago, IL, 60614

$3,200,000

230 W Saint Paul Ave, Chicago, IL, 60614

2-4 Units

Beds: --
Baths: --
Size: -- sqft

Est. Rent: N/A
Est. Cash Flow: N/A
Modeled Cost: N/A
Estimate Confidence: N/A
Rent Source: N/A

Est. P&I: $15,894/mo

2617 S Shields Ave, Chicago, IL, 60616

$500,000

2617 S Shields Ave, Chicago, IL, 60616

Duplex

Beds: --
Baths: --
Size: -- sqft

Est. Rent: N/A
Est. Cash Flow: N/A
Modeled Cost: N/A
Estimate Confidence: N/A
Rent Source: N/A

Est. P&I: $2,483/mo

2526 W Monroe St, Chicago, IL, 60612

$599,999

2526 W Monroe St, Chicago, IL, 60612

Duplex

Beds: --
Baths: --
Size: -- sqft

Est. Rent: N/A
Est. Cash Flow: N/A
Modeled Cost: N/A
Estimate Confidence: N/A
Rent Source: N/A

Est. P&I: $2,980/mo

2622 N Central Park Ave, Chicago, IL, 60647

$975,000

2622 N Central Park Ave, Chicago, IL, 60647

Duplex

Beds: 9
Baths: 4.5
Size: -- sqft

Est. Rent: N/A
Est. Cash Flow: N/A
Modeled Cost: N/A
Estimate Confidence: N/A
Rent Source: N/A

Est. P&I: $4,843/mo

$0

1437 W Augusta Blvd, Chicago, IL, 60642

2-4 Units

Beds: 7
Baths: 3
Size: -- sqft

Est. Rent: N/A
Est. Cash Flow: N/A
Modeled Cost: N/A
Estimate Confidence: N/A
Rent Source: N/A

Est. P&I: $0/mo

$0

6025 S Prairie Ave, Chicago, IL, 60637

2-4 Units

Beds: --
Baths: --
Size: -- sqft

Est. Rent: N/A
Est. Cash Flow: N/A
Modeled Cost: N/A
Estimate Confidence: N/A
Rent Source: N/A

Est. P&I: $0/mo

$0

6029 S Prairie Ave, Chicago, IL, 60637

2-4 Units

Beds: --
Baths: --
Size: -- sqft

Est. Rent: N/A
Est. Cash Flow: N/A
Modeled Cost: N/A
Estimate Confidence: N/A
Rent Source: N/A

Est. P&I: $0/mo

$550,000

3621 W 5th Ave, Chicago, IL, 60624

2-4 Units

Beds: --
Baths: --
Size: -- sqft

Est. Rent: N/A
Est. Cash Flow: N/A
Modeled Cost: N/A
Estimate Confidence: N/A
Rent Source: N/A

Est. P&I: $2,732/mo