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View PropertiesAs of Apr, 27 2026
Rabbu ROI Score
Chicago offers attractive short-term rental potential, with a balance of healthy demand and revenue relative to property values.
Chicago's short-term rental market presents an attractive opportunity for investors, backed by 2,754 active Airbnb listings and average annual revenue of $33,268 per property. With an ADR of $171 — well below the Illinois state average of $319 — and above-average occupancy stability, the market rewards operators who price competitively and capitalize on the city's deep well of tourism, convention, and event-driven demand. Larger properties in particular stand out, with 5-bedroom and 6+ bedroom units generating annual revenues approaching or exceeding $100,000.
According to Rabbu market data, the Chicago short-term rental market shows:
| Metric | Context | Value |
|---|---|---|
| Active Airbnb Listings | As of Apr, 27 2026 | 2,754 |
| Average Daily Rate (ADR) | vs. $319 state avg. | $171 |
| Average Occupancy Rate | vs. 33% state avg. | 33% |
| RevPAN | ADR * Occupancy Rate | $56 |
| Average Monthly Revenue | Historical 12-month average | $2,772 |
| Average Annual Revenue | Historical 12-month average | $33,268 |
Data sources: Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Mar, 17 2026.
Chicago's blend of year-round demand drivers — from business travel and conventions to summer tourism and a thriving food and culture scene — gives STR investors a diversified revenue base that few Midwest markets can match.
Key investment factors
"With an ROI score of 66 out of 100, Chicago earns an "Attractive Opportunity" designation — a market where healthy demand and reasonable property costs create a solid entry point for STR investors. Seasonality is pronounced: revenue peaks sharply in June at $4,288 per month and dips to roughly $1,116 in February, so investors should plan for meaningful winter softness. The market's above-average occupancy stability is a notable strength, helping to smooth out returns even during slower stretches. Overall, the opportunity is strongest for investors targeting larger multi-bedroom properties in high-demand neighborhoods, where annual revenue potential can meaningfully outpace the market average."
— Rabbu Market Analysis Team
Chicago's STR revenue follows a sharp seasonal curve, peaking in June at $4,288 and bottoming out in February at $1,116 — nearly a 4× spread. The May-through-October stretch consistently delivers above-average monthly returns, making summer and early fall the critical earning window for investors.
| Month | Trend | Revenue |
|---|---|---|
| January |
|
$1,148 |
| February |
|
$1,116 |
| March |
|
$2,108 |
| April |
|
$2,266 |
| May |
|
$3,544 |
| June |
|
$4,288 |
| July |
|
$3,918 |
| August |
|
$3,819 |
| September |
|
$3,349 |
| October |
|
$3,532 |
| November |
|
$2,263 |
| December |
|
$1,911 |
One-bedroom units dominate Chicago's supply at 1,001 listings, followed closely by 2-bedroom properties (891), while larger configurations of 5 bedrooms and above account for fewer than 100 listings combined. This relative scarcity of bigger properties could signal opportunity for investors willing to target the higher end of the market.
| Size | Trend | Value |
|---|---|---|
| Studio |
|
142 |
| 1 bedroom |
|
1,001 |
| 2 bedrooms |
|
891 |
| 3 bedrooms |
|
470 |
| 4 bedrooms |
|
151 |
| 5 bedrooms |
|
49 |
| 6+ bedrooms |
|
50 |
ADR scales sharply with property size in Chicago, from $106 for 1-bedroom units up to $599 for 6+ bedrooms. The most dramatic per-bedroom premium kicks in between 3-bedroom ($222) and 4-bedroom ($325) properties, suggesting that moving beyond three bedrooms significantly boosts nightly pricing power.
| Size | Trend | Value |
|---|---|---|
| Studio |
|
$131 |
| 1 bedroom |
|
$106 |
| 2 bedrooms |
|
$157 |
| 3 bedrooms |
|
$222 |
| 4 bedrooms |
|
$325 |
| 5 bedrooms |
|
$462 |
| 6+ bedrooms |
|
$599 |
Revenue per available night climbs steadily with size, from $37 for 1-bedroom units to $184 for 6+ bedroom properties. Four-bedroom and larger listings deliver RevPAN well above the market average of $56, indicating that bigger properties translate their higher ADR into meaningfully stronger per-night returns even after accounting for occupancy.
| Size | Trend | Value |
|---|---|---|
| Studio |
|
$47 |
| 1 bedroom |
|
$37 |
| 2 bedrooms |
|
$51 |
| 3 bedrooms |
|
$63 |
| 4 bedrooms |
|
$98 |
| 5 bedrooms |
|
$156 |
| 6+ bedrooms |
|
$184 |
Occupancy rates are relatively compressed across property sizes, ranging from 28% for 3-bedroom units to 36% for studios. Smaller units (studios and 1-bedrooms) stay slightly fuller, which can provide more consistent booking flow for investors prioritizing cash-flow stability over peak revenue.
| Size | Trend | Value |
|---|---|---|
| Studio |
|
36% |
| 1 bedroom |
|
35% |
| 2 bedrooms |
|
33% |
| 3 bedrooms |
|
28% |
| 4 bedrooms |
|
30% |
| 5 bedrooms |
|
34% |
| 6+ bedrooms |
|
31% |
Monthly revenue differences are dramatic: 1-bedroom and studio listings average around $1,850 per month, while 6+ bedroom properties bring in $8,577 — more than 4× as much. The jump from 3-bedroom ($3,440) to 4-bedroom ($6,184) properties represents a particularly notable inflection point for investors seeking higher returns.
| Size | Trend | Value |
|---|---|---|
| Studio |
|
$1,850 |
| 1 bedroom |
|
$1,846 |
| 2 bedrooms |
|
$3,200 |
| 3 bedrooms |
|
$3,440 |
| 4 bedrooms |
|
$6,184 |
| 5 bedrooms |
|
$8,229 |
| 6+ bedrooms |
|
$8,577 |
Annual revenue potential increases substantially with size, ranging from roughly $22,000 for studios and 1-bedrooms to over $102,900 for 6+ bedroom properties. Five-bedroom units at $98,759 and 4-bedroom units at $74,212 also stand out as strong revenue generators, offering investors attractive return potential relative to the market-wide average of $33,268.
| Size | Trend | Value |
|---|---|---|
| Studio |
|
$22,201 |
| 1 bedroom |
|
$22,156 |
| 2 bedrooms |
|
$38,408 |
| 3 bedrooms |
|
$41,290 |
| 4 bedrooms |
|
$74,212 |
| 5 bedrooms |
|
$98,759 |
| 6+ bedrooms |
|
$102,926 |
Kitchens (96%), parking (85%), and self check-in (84%) are near-universal among Chicago listings, signaling that guests expect a home-like, convenient experience as the baseline. Amenities like a dedicated workspace (73%) and washer/dryer (75–77%) also show high adoption, reflecting demand from both leisure and business travelers who expect full-service accommodations.
| Amenity | Trend | Value |
|---|---|---|
| Kitchen |
|
96% |
| Parking |
|
85% |
| Self Check-in |
|
84% |
| Washer |
|
77% |
| Dryer |
|
75% |
| Workspace |
|
73% |
| Patio or Balcony |
|
43% |
| Outdoor Furniture |
|
33% |
| Backyard |
|
32% |
| Pets |
|
30% |
| BBQ Grill |
|
26% |
| Gym |
|
14% |
| Lake Access |
|
7% |
| EV Charger |
|
5% |
Rabbu's ROI Score is a proprietary metric that evaluates short-term rental investment potential based on multiple factors.
| Factor | Chicago Performance | Weight |
|---|---|---|
| Revenue-to-Price Ratio | Average | 40% |
| Occupancy Stability | Above average | 30% |
| Market Growth Trend | Average | 15% |
| Supply/Demand Balance | Average | 15% |
Chicago's ROI score of 66 out of 100 places it in the "Attractive Opportunity" band, reflecting a market where revenue-to-price ratios are average but above-average occupancy stability helps de-risk the investment. Market growth trends and supply/demand balance both register as average, suggesting a maturing but still healthy competitive landscape. Pairing this score with thorough research into Chicago's licensing requirements and neighborhood-level performance data will give investors the clearest picture of where specific opportunities lie.
Understanding local STR regulations is essential before investing in Chicago. Here's the current regulatory landscape:
Chicago requires short-term rental operators to register with the city and obtain the appropriate license, which may include a Shared Housing Unit Registration or a Vacation Rental license depending on how the property is used. Investors should verify current permit requirements directly with the City of Chicago's Department of Business Affairs and Consumer Protection before listing.
Common restrictions in Chicago's STR regulatory framework include occupancy limits, minimum stay requirements in certain zones, noise and nuisance ordinances, and rules around parking availability. Some buildings and HOAs impose additional restrictions or outright bans on short-term rentals, so reviewing association bylaws is an essential step before purchasing a property for STR use.
Short-term rental hosts in Illinois are generally subject to state and local occupancy taxes, including Chicago's Hotel Accommodations Tax and the state's Hotel Operators' Occupation Tax. Major booking platforms typically collect and remit many of these taxes on behalf of hosts, but operators should confirm their full tax obligations with a local tax professional.
Regulations subject to change. Always verify with local authorities before purchasing. A Rabbu partner agent specializing in Chicago can provide current regulatory guidance.
Financing an Airbnb investment in Chicago requires lenders who understand STR income. Rabbu partner lenders offer:
"Over the next 12–18 months, Chicago's STR market is expected to maintain steady demand supported by the city's robust event calendar, corporate travel, and lakefront tourism. Seasonal revenue data suggests summer months (June–August) will continue to anchor annual performance, though shoulder months like May and October already show healthy earnings in the $3,500+ range. ADR growth of 1–3% is a reasonable estimate given average market growth trends, while occupancy is likely to hold in the 30–35% range market-wide. Investors entering now can position for relatively predictable cash flow, though winter softness from January through February should be factored into projections."
— Rabbu Market Analysis Team
Rabbu provides Airbnb and short-term rental market data and statistics across the United States. Our mission is to empower investors with accurate insights and easy-to-use tools, so they can confidently identify and act on the best opportunities in the Airbnb market.
Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Mar, 17 2026. Revenue projections are estimates based on comparable properties and do not guarantee future performance. Data reflects trailing performance as of April 2026 and may not capture very recent market shifts. Local regulations, HOA rules, and tax obligations can change; investors should verify current requirements with local authorities before purchasing.
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