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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

3.5%

Avg Cash on Cash

-8.3%

Median Cashflow

-$698/mo

Avg Rent Estimate

$3,832/mo

Avg Price

$392,825

Price Range

$134,999 - $850,000

Rent to Price

0.98%

okay ratio

Positive Cashflow

26%

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 3.5%, 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 -$698 with an average estimated nightly-rate-adjusted revenue of $3,832/month. These figures reflect real property data, not projections.

6524 N Oshkosh Ave, Chicago, IL 60631

Price

$489,900

Rent

$3,545

CachFlow

-$1,295

CoC

-12.86

Full Analysis

6505 S Woodlawn Ave, Chicago, IL 60637

Price

$549,900

Rent

$2,997

CachFlow

-$1,815

CoC

-16.32

Full Analysis

10211 S Eberhart Ave, Chicago, IL 60628

Price

$223,800

Rent

$2,119

CachFlow

-$253

CoC

-4.67

Full Analysis

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
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Chicago, IL Airbnb Market Insights

  • Median cashflow is -$698/month — careful deal selection is essential here
  • 3.5% median cap rate is typical of appreciation-focused markets
  • At 26% 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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