Investor market data · Illinois

Chicago, IL Rental Market for Investors

An estimated 65% of Chicago's active listings could cash-flow as a short-term rental — here's what the numbers say for investors, as of August 2026.

See what pencils →Run a DSCR

$425,000Median list price2,927 active listings

$54,935Median STR revenue / yrprojected, gross

Homes in Chicago that pencil right now

A sample of active Chicago listings whose DSCR clears 1.25 using short-term rental income projections we accept as a direct lender. These are spread across the price range, not ranked, and current as of August 2026.

$126,000DSCR 1.42
1 bed · 1 bath · 800 sqft
Condo in 60660 · built 1951
STR revenue
$32,149/yr
Est. interest-only payment
$1,511/mo
On the market 143 days · Listed by CENTURY 21 S.G.R., Inc.
Scout this home & market: 1-bed condo in Chicago
$215,000DSCR 1.68
2 bed · 2 bath · 1,100 sqft
Condo in 60626 · built 1972
STR revenue
$39,474/yr
Est. interest-only payment
$1,566/mo
On the market 59 days · Listed by Baird & Warner La Grange
Scout this home & market: 2-bed condo in Chicago
$284,900DSCR 1.54
4 bed · 2 bath · 1,300 sqft
House in 60638 · built 1958
STR revenue
$45,942/yr
Est. interest-only payment
$1,985/mo
On the market 18 days · Listed by GenStone Realty
Scout this home & market: 4-bed house in Chicago
$415,000DSCR 1.65
2 bed · 2 bath · 1,200 sqft
Condo in 60607 · built 2000
STR revenue
$78,311/yr
Est. interest-only payment
$3,158/mo
On the market 11 days · Listed by Real Broker LLC
Scout this home & market: 2-bed condo in Chicago
$435,000DSCR 1.58
2 bed · 2 bath · 1,600 sqft
Condo in 60611 · built 1969
STR revenue
$95,547/yr
Est. interest-only payment
$4,039/mo
On the market 13 days · Listed by @properties Gold Coast
Scout this home & market: 2-bed condo in Chicago
$475,000DSCR 1.47
2 bed · 2 bath · 1,350 sqft
Condo in 60654 · built 1920
STR revenue
$91,911/yr
Est. interest-only payment
$4,178/mo
On the market 23 days · Listed by Brilliant Real Estate
Scout this home & market: 2-bed condo in Chicago
$524,900DSCR 1.30
2 bed · 2.5 bath · 1,550 sqft
Condo in 60607 · built 1911
STR revenue
$77,871/yr
Est. interest-only payment
$4,002/mo
On the market 24 days · Listed by COMPASS
Scout this home & market: 2-bed condo in Chicago
$599,900DSCR 1.28
2 bed · 2 bath · 1,497 sqft
Condo in 60603 · built 2009
STR revenue
$110,036/yr
Est. interest-only payment
$5,718/mo
On the market 159 days · Listed by @properties Christie's International Real Estate
Scout this home & market: 2-bed condo in Chicago

Ask about Chicago deals →Run any address yourself

As of August 2026, we analyzed 2,927 active for-sale homes in Chicago, Illinois. The typical listing is priced at $425,000 and is projected to generate about $54,935 a year as a short-term rental.

After setting aside an estimated 20% for operating costs, an estimated 65.3% of those homes could still cover an investor mortgage payment on short-term-rental income — well above the 52.5% median across the 200 major metros we track, ranking Chicago #45 of 200 for cash-flow potential.

On market momentum: homes in Chicago sit a median of 40 days on the market, and 37% of active listings came on in just the last 30 days — a fast-moving market, which shapes how much room there is to negotiate.

For a DSCR loan — which qualifies on the property's rental income rather than your personal income — that's a relatively healthy setup: in Chicago, a meaningful share of listings throw off enough short-term-rental income, after costs, to cover an estimated investor mortgage payment.

What actually works in Chicago

Chicago works for investors, but the window is specific: 650 of the 1,935 Chicago homes, condos and townhomes we can price confidently clear a DSCR of 1.25. Nine in ten of them are priced under $525,000.

Share of those listings clearing an DSCR of 1.25, by price and bedroom count. The smaller figure is the median DSCR for that group.
Price	1 bed	2 bed	3 bed	4 bed	5 bed
$150k–$250k	43%1.22	64%1.36	82%1.51	98%1.92	100%2.84
$250k–$350k	29%1.08	41%1.15	37%1.18	73%1.47	100%1.90
$350k–$500k	0%0.82	48%1.23	12%0.98	43%1.17	71%1.49
$500k+	0%0.47	13%0.91	8%0.78	9%0.79	30%0.84

Darker means a larger share of that group cash-flows. “—” means fewer than 8 active listings — too few to draw a conclusion from.

Chicago in full

Active for-sale homes analyzed	2,927
Median list price	$425,000
Median projected STR revenue (annual, gross)	$54,935
Median average daily rate (ADR)	$280
Median occupancy	58%
Median beds	3
Median size	1,487 sqft
Estimated cash-flow-positive share	65.3%
Median days on market	40 days
New listings (last 30 days)	37.3% of active