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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

3.7%

Avg Cash on Cash

-4.7%

Median Cashflow

-$757/mo

Avg Rent Estimate

$2,763/mo

Avg Price

$331,213

Price Range

$64,900 - $549,900

Rent to Price

0.83%

okay ratio

Positive Cashflow

31%

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 3.7%, the mid-to-upper tier property prices reflect strong underlying demand. STR investors here typically benefit from appreciation alongside rental income.

Across 15+ analyzed properties, Chicago, IL STR investments show a median monthly cashflow of -$757 with an average estimated nightly-rate-adjusted revenue of $2,763/month. These figures reflect real property data, not projections.

4820 N Kentucky Ave, Chicago, IL 60630

Price

$462,500

Rent

$2,602

CachFlow

-$1,654

CoC

-17.24

Full Analysis

6717 S Rhodes Ave, Chicago, IL 60637

Price

$64,900

Rent

$2,131

CachFlow

$604

CoC

22.92

Full Analysis

8128 S Komensky Ave, Chicago, IL 60652

Price

$334,200

Rent

$1,758

CachFlow

-$1,202

CoC

-16.36

Full Analysis

7935 S Blackstone Ave, Chicago, IL 60619

Price

$199,000

Rent

$2,411

CachFlow

-$48

CoC

-0.96

Full Analysis

6524 N Oshkosh Ave, Chicago, IL 60631

Price

$489,900

Rent

$3,545

CachFlow

-$1,295

CoC

-12.86

Full Analysis
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Chicago, IL Airbnb Market Insights

  • Median cashflow is -$757/month — careful deal selection is essential here
  • 3.7% median cap rate is typical of appreciation-focused markets
  • At 31% positive cashflow rate, Chicago, IL requires selective property picks
  • Mid-to-upper tier market with properties from $64,900 to $549,900
  • Consider this market if your strategy favors equity growth with rental income covering holding costs

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