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Chicago, IL Short-Term Rental / Airbnb Analysis

Analyze rental property cap rates, cash-on-cash returns, and cashflow for short-term rental / airbnb investments in Chicago, IL. Based on 15+ datapoints.

Chicago, IL Short-Term Rental / Airbnb Investment Snapshot

Based on 15+ short-term rental / airbnb datapoints

Median Cap Rate

4%

Avg Cash on Cash

-11%

Median Cashflow

-$565/mo

Avg Rent Estimate

$2,325/mo

Avg Price

$268,815

Price Range

$75K – $450K

approximate

Rent to Price

0.86%

okay ratio

Positive Cashflow

8%

of analyzed properties

Recent real estate investor listings analysed as short-term rental / airbnb deals in Chicago, IL

Chicago, IL is an emerging short-term rental market with growing investor interest. With 15+ datapoints analyzed so far, early metrics suggest opportunity for Airbnb investors willing to enter before the market matures. Current average cash-on-cash returns sit at -11%.

Across 15+ analyzed properties, Chicago, IL STR investments show a median monthly cashflow of -$565 with an average estimated nightly-rate-adjusted revenue of $2,325/month. These figures reflect real property data, not projections.

8955 S May St, Chicago, IL 60620

Price

$223,700

Rent

$1,618

CachFlow

-$622

CoC

-11.49

Full Analysis

8931 S Bennett Ave, Chicago, IL 60617

Price

$256,800

Rent

$2,494

CachFlow

-$479

CoC

-7.99

Full Analysis

8326 S Indiana Ave, Chicago, IL 60619

Price

$272,695

Rent

$1,754

CachFlow

-$902

CoC

-14.38

Full Analysis

9347 S Wallace St, Chicago, IL 60620

Price

$299,000

Rent

$2,090

CachFlow

-$868

CoC

-12.89

Full Analysis

13227 S Escanaba Ave, Chicago, IL 60633

Price

$252,900

Rent

$1,813

CachFlow

-$828

CoC

-13.97

Full Analysis
1–5 of 10+
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Chicago, IL Airbnb Market Insights

  • Median cashflow is -$565/month — careful deal selection is essential here
  • 4% median cap rate is typical of appreciation-focused markets
  • At 8% positive cashflow rate, Chicago, IL requires selective property picks
  • Moderately priced market with properties priced about $75,000 to $450,000
  • Early-stage market data — revisit as more properties are analyzed for stronger signals

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