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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 20+ datapoints.

Chicago, IL Short-Term Rental / Airbnb Investment Snapshot

Based on 20+ short-term rental / airbnb datapoints

Median Cap Rate

3.6%

Avg Cash on Cash

-9.3%

Median Cashflow

-$676/mo

Avg Rent Estimate

$4,216/mo

Avg Price

$412,514

Price Range

$157,300 - $850,000

Rent to Price

1.02%

strong ratio

Positive Cashflow

25%

of analyzed properties

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

Chicago, IL is a premium short-term rental market where property values drive long-term wealth. While cap rates are modest at 3.6%, the premium property prices reflect strong underlying demand. STR investors here typically benefit from appreciation alongside rental income.

Across 20+ analyzed properties, Chicago, IL STR investments show a median monthly cashflow of -$676 with an average estimated nightly-rate-adjusted revenue of $4,216/month. These figures reflect real property data, not projections.

1937 W Melrose St, Chicago, IL 60657

Price

$1,599,000

Rent

$8,048

CachFlow

-$6,621

CoC

-22.08

Full Analysis

968 W Cuyler Ave, Chicago, IL 60613

Price

$1,050,000

Rent

$6,116

CachFlow

-$3,676

CoC

-18.5

Full Analysis

2030 W Shakespeare Ave, Chicago, IL 60647

Price

$850,000

Rent

$4,678

CachFlow

-$3,144

CoC

-19.2

Full Analysis

3648 W 68th Pl, Chicago, IL 60629

Price

$269,000

Rent

$2,457

CachFlow

-$533

CoC

-8.59

Full Analysis

1934 N Bissell St, Chicago, IL 60614

Price

$1,799,900

Rent

$5,840

CachFlow

-$8,732

CoC

-26.07

Full Analysis
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Chicago, IL Airbnb Market Insights

  • Median cashflow is -$676/month — careful deal selection is essential here
  • 3.6% median cap rate is typical of appreciation-focused markets
  • At 25% positive cashflow rate, Chicago, IL requires selective property picks
  • Premium market with properties from $157,300 to $850,000
  • Consider this market if your strategy favors equity growth with rental income covering holding costs

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