REI Lense

REI Lense

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

4%

Avg Cash on Cash

-7.2%

Median Cashflow

-$463/mo

Avg Rent Estimate

$4,125/mo

Avg Price

$430,681

Price Range

$199,000 - $874,400

Rent to Price

0.96%

okay 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 4%, 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 -$463 with an average estimated nightly-rate-adjusted revenue of $4,125/month. These figures reflect real property data, not projections.

2928 N Rutherford Ave, Chicago, IL 60634

Price

$480,000

Rent

$5,194

CachFlow

-$375

CoC

-3.61

Full Analysis

5231 N Lakewood Ave, Chicago, IL 60640

Price

$1,150,000

Rent

$5,088

CachFlow

-$4,930

CoC

-22.28

Full Analysis

6600 N Lehigh Ave, Chicago, IL 60646

Price

$599,900

Rent

$4,191

CachFlow

-$1,912

CoC

-15.94

Full Analysis

10344 S Leavitt St, Chicago, IL 60643

Price

$319,900

Rent

$2,968

CachFlow

-$931

CoC

-13.12

Full Analysis

5021 W Berenice Ave, Chicago, IL 60641

Price

$599,900

Rent

$2,654

CachFlow

-$2,752

CoC

-22.02

Full Analysis

Chicago, IL Airbnb Market Insights

  • Median cashflow is -$463/month — careful deal selection is essential here
  • 4% median cap rate is typical of appreciation-focused markets
  • At 29% positive cashflow rate, Chicago, IL requires selective property picks
  • Premium market with properties from $199,000 to $874,400
  • Consider this market if your strategy favors equity growth with rental income covering holding costs

Enter a Property Address for Instant Investment Analysis

Fast and accurate real estate investment analysis