Chicago, IL Rental Market for Investors
An estimated 66% of Chicago's active listings could cash-flow as a short-term rental — here's what the numbers say for investors, as of October 2026.
As of October 2026, we analyzed 3,103 active for-sale homes in Chicago, Illinois. The typical listing is priced at $414,900 and is projected to generate about $53,605 a year as a short-term rental.
After setting aside an estimated 20% for operating costs, an estimated 66.0% of those homes could still cover an investor mortgage payment on short-term-rental income — well above the 53.1% median across the 200 major metros we track, ranking Chicago #41 of 200 for cash-flow potential.
On market momentum: homes in Chicago sit a median of 35 days on the market, and 40% 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: 725 of the 2,099 Chicago homes, condos and townhomes we can price confidently clear a DSCR of 1.25. Nine in ten of them are priced under $533,000.
| Price | 1 bed | 2 bed | 3 bed | 4 bed | 5 bed |
|---|---|---|---|---|---|
| Under $150k | — | — | 100%2.14 | — | — |
| $150k–$250k | 45%1.23 | 55%1.32 | 84%1.54 | 94%2.04 | — |
| $250k–$350k | 27%1.07 | 44%1.19 | 37%1.18 | 76%1.43 | 100%1.73 |
| $350k–$500k | 0%0.83 | 50%1.24 | 10%0.92 | 34%1.17 | 84%1.53 |
| $500k+ | 0%0.69 | 13%0.90 | 12%0.82 | 10%0.79 | 25%0.88 |
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 | 3,103 |
|---|---|
| Median list price | $414,900 |
| Median projected STR revenue (annual, gross) | $53,605 |
| Median average daily rate (ADR) | $273 |
| Median occupancy | 58% |
| Median beds | 3 |
| Median size | 1,430 sqft |
| Estimated cash-flow-positive share | 66.0% |
| Median days on market | 35 days |
| New listings (last 30 days) | 39.9% of active |
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Estimates for educational purposes. Final terms subject to credit, property & program approval.
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