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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 30+ datapoints.

Chicago, IL Short-Term Rental / Airbnb Investment Snapshot

Based on 30+ short-term rental / airbnb datapoints

Median Cap Rate

3.6%

Avg Cash on Cash

-8%

Median Cashflow

-$577/mo

Avg Rent Estimate

$3,918/mo

Avg Price

$389,890

Price Range

$134,999 - $850,000

Rent to Price

1%

strong ratio

Positive Cashflow

29%

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 mid-to-upper tier property prices reflect strong underlying demand. STR investors here typically benefit from appreciation alongside rental income.

Across 30+ analyzed properties, Chicago, IL STR investments show a median monthly cashflow of -$577 with an average estimated nightly-rate-adjusted revenue of $3,918/month. These figures reflect real property data, not projections.

9018 S Brandon Ave, Chicago, IL 60617

Price

$237,500

Rent

$4,180

CachFlow

$700

CoC

12.38

Full Analysis

4100 W 81st St, Chicago, IL 60652

Price

$374,600

Rent

$2,429

CachFlow

-$937

CoC

-11.63

Full Analysis

4212 N Mozart St, Chicago, IL 60618

Price

$500,000

Rent

$3,720

CachFlow

-$1,327

CoC

-12.95

Full Analysis

11163 S Trumbull Ave, Chicago, IL 60655

Price

$386,000

Rent

$2,660

CachFlow

-$990

CoC

-11.99

Full Analysis

1837 W 104th St, Chicago, IL 60643

Price

$545,900

Rent

$2,855

CachFlow

-$1,677

CoC

-15.17

Full Analysis
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Chicago, IL Airbnb Market Insights

  • Median cashflow is -$577/month — careful deal selection is essential here
  • 3.6% median cap rate is typical of appreciation-focused markets
  • At 29% positive cashflow rate, Chicago, IL requires selective property picks
  • Mid-to-upper tier market with properties from $134,999 to $850,000
  • Consider this market if your strategy favors equity growth with rental income covering holding costs

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