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Chicago, IL Mid-Term Rental Analysis

Analyze rental property cap rates, cash-on-cash returns, and cashflow for mid-term rental investments in Chicago, IL. Based on 100+ datapoints.

Chicago, IL Mid-Term Rental Investment Snapshot

Based on 100+ mid-term rental datapoints

Median Cap Rate

6.9%

Avg Cash on Cash

3.7%

Median Cashflow

$269/mo

Avg Rent Estimate

$3,798/mo

Avg Price

$366,420

Price Range

$60,000 - $757,900

Rent to Price

1.04%

strong ratio

Positive Cashflow

63%

of analyzed properties

Recent real estate investor listings analysed as mid-term rental deals in Chicago, IL

Chicago, IL presents a balanced mid-term rental profile across 100+ analyzed datapoints. A median 6.9% cap rate combined with 3.7% average cash-on-cash returns make this a solid market for investors blending furnished-rental yield with the operational simplicity of monthly stays at a mid-to-upper tier price point.

Across 100+ analyzed properties, Chicago, IL mid-term rental investments show a median monthly cashflow of $269 with average furnished rent estimates of $3,798/month. These figures reflect real property data, not projections.

5659 N Olcott Ave, Chicago, IL 60631

Price

$586,600

Rent

$4,418

CachFlow

-$796

CoC

-6.77

Full Analysis

1851 N Natoma Ave, Chicago, IL 60707

Price

$446,500

Rent

$3,868

CachFlow

-$550

CoC

-5.91

Full Analysis

5928 W Grace St, Chicago, IL 60634

Price

$481,000

Rent

$4,659

CachFlow

-$46

CoC

-0.46

Full Analysis

8844 S Halsted St, Chicago, IL 60620

Price

$279,500

Rent

$3,460

CachFlow

$580

CoC

9.07

Full Analysis

5712 S Nashville Ave, Chicago, IL 60638

Price

$472,100

Rent

$4,350

CachFlow

-$318

CoC

-3.26

Full Analysis
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Chicago, IL Mid-Term Rental Market Insights

  • Positive median cashflow of $269/month indicates most investors cover expenses
  • 6.9% median cap rate reflects a balanced risk-return profile
  • 63% positive cashflow rate means roughly half properties are cash-flow positive
  • Mid-to-upper tier market with properties from $60,000 to $757,900

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