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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 10+ datapoints.

Chicago, IL Short-Term Rental / Airbnb Investment Snapshot

Based on 10+ short-term rental / airbnb datapoints

Median Cap Rate

3.2%

Avg Cash on Cash

-9.6%

Median Cashflow

-$956/mo

Avg Rent Estimate

$2,535/mo

Avg Price

$325,300

Price Range

$64,900 - $549,900

Rent to Price

0.78%

okay ratio

Positive Cashflow

17%

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 3.2%, the mid-to-upper tier property prices reflect strong underlying demand. STR investors here typically benefit from appreciation alongside rental income.

Across 10+ analyzed properties, Chicago, IL STR investments show a median monthly cashflow of -$956 with an average estimated nightly-rate-adjusted revenue of $2,535/month. These figures reflect real property data, not projections.

11028 S Sawyer Ave, Chicago, IL 60655

Price

$302,300

Rent

$2,169

CachFlow

-$976

CoC

-14.37

Full Analysis

6705 N Sacramento Ave, Chicago, IL 60645

Price

$450,000

Rent

$1,949

CachFlow

-$1,600

CoC

-17.07

Full Analysis

1336 E 71st Pl, Chicago, IL 60619

Price

$215,000

Rent

$2,135

CachFlow

-$327

CoC

-6.21

Full Analysis

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
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Chicago, IL Airbnb Market Insights

  • Median cashflow is -$956/month — careful deal selection is essential here
  • 3.2% median cap rate is typical of appreciation-focused markets
  • At 17% 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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