Chicago, IL Short-Term Rental ROI Calculator
Analyze your Airbnb investment with live Chicago market data. Pre-populated with real ADR, occupancy, and revenue benchmarks.
Investor Quick Take
Strengths
- Competitive ADR — $198/night market rate
- Accessible entry point — median home $385K
Risks
- Moderate seasonality — plan for slower months
- Heavily regulated market — permits required, zone restrictions
Moderate Market
Based on ADR, occupancy, and supply metrics
Chicago is a urban market with 57% average occupancy and $198 ADR.
We've pre-populated this calculator with Chicago's market averages. Adjust the values to match your specific property.
Chicago Short-Term Rental Market Overview
Chicago draws consistent STR demand from business travelers, event tourism, and weekend visitors. As Illinois's major urban center, the city generates year-round occupancy that insulates investors from the seasonal volatility common in resort markets.
The average STR in Chicago generates approximately $41,200 in annual revenue, with an average daily rate of $198 and a 57% occupancy rate across the year. These metrics position Chicago as a solid mid-tier STR market — particularly attractive to investors seeking consistent year-round cash flow.
Active listings in Chicago grew by 4% year-over-year, currently sitting at approximately 9,200 active STR units. This moderate growth rate suggests a market finding equilibrium between supply and demand, which typically supports stable occupancy and ADR. Investors should track supply trends quarterly using tools like AirDNA or Rabbu before committing capital.
Key considerations for Chicago investors: regulatory risk is rated high — Chicago has active regulation, permit requirements, or zoning restrictions that limit STR operations. Verify current rules with the city before purchasing. Property management costs, cleaning turnover for short stays, and platform fee optimization are the primary levers operators use to improve net margin in this market.
Market Metrics
Chicago Airbnb Revenue by Property Size
| Property Size | Avg ADR | Avg Occupancy | Avg Annual Revenue | Est. Cap Rate Range |
|---|---|---|---|---|
| Studio | $109 | 57% | $23K | 2.8–3.7% |
| 1BR | $150 | 57% | $31K | 3.8–5.1% |
| 2BR | $218 | 57% | $47K | 5.8–7.8% |
| 3BR | $287 | 57% | $64K | 7.8–10.5% |
| 4BR+ | $396 | 57% | $87K | 10.5–14.2% |
Chicago STR Revenue Calendar
Seasonal Insight: Peak season runs October, April, and May. Expect up to 15% higher revenue during peak months. Plan for January and December as your slowest period — approximately 20% below the annual average.
Is Chicago a Good Market for Short-Term Rentals?
Why investors choose Chicago
- ✓Solid revenue potential: market average of $41,200 per year with upside for well-managed properties
- ✓Reliable occupancy: 57% market average provides predictable income baseline
- ✓Year-round demand: Chicago's diverse visitor base prevents the seasonal cliffs common in resort markets
- ✓Growing market: 4% annual listing growth signals strong investor and visitor confidence
Key risks to consider
- !Regulatory risk: Chicago has active STR restrictions — permits, zoning, or operational limits may constrain your strategy
- !High acquisition cost: median home values make achieving target cash-on-cash returns challenging without creative financing
Chicago STR Regulatory Overview
HighChicago has significant STR regulation. Shared housing (home-sharing) and vacation rentals require separate licenses. Non-owner-occupied rentals face significant restrictions in residential areas, and aldermanic approval is often required.
Key Requirements
- ·Vacation rental license or shared housing license (different requirements)
- ·Aldermanic restrictions in many wards
- ·Condo building opt-in requirement
- ·Chicago hotel accommodation tax
Source: City of Chicago Department of Business Affairs · Last verified: 2026-01. Regulations change frequently — always verify current requirements with local authorities before investing.
Compare Chicago to Similar Markets
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| Metric | Chicago | Branson | Lake of the Ozarks | Traverse City |
|---|---|---|---|---|
| ADR | $198 | $142 | $178 | $198 |
| Occupancy | 57% | 58% | 52% | 50% |
| Avg Revenue | $41K | $30K | $34K | $36K |
| Median Home Value | $385K | $245K | $285K | $395K |
| Regulatory Risk | High | Low | Low | Low |
Chicago Short-Term Rental FAQs
Is Chicago a good market for short-term rentals?+
Chicago, IL is a solid US STR markets. With an average daily rate of $198 and 57% occupancy, the average listing earns approximately $41,200 per year. Market performance varies significantly by property type, location within the city, and management quality — this calculator helps you model your specific scenario.
What is the average Airbnb income in Chicago?+
The average STR listing in Chicago generates approximately $41,200 in gross annual revenue at a $198 average daily rate and 57% occupancy. Top-performing listings with premium amenities, strong reviews, and professional management can earn 30–50% above the market average. After platform fees (3–5%), cleaning costs, and other expenses, net revenue typically ranges 60–75% of gross.
What occupancy rate can I expect for an Airbnb in Chicago?+
The market-average occupancy in Chicago is approximately 57%. New listings typically underperform the market average for the first 3–6 months while accumulating reviews. Properties with professional photography, competitive pricing, and consistently high ratings can reach 69–75% occupancy. This market is moderately seasonal — consistent occupancy is achievable year-round with good pricing strategy.
What are the STR regulations in Chicago?+
Regulatory risk in Chicago is rated High. Chicago has enacted significant STR restrictions. Investors must research current zoning, permit requirements, and any owner-occupancy rules before purchasing. Violations can result in substantial fines. Regulations change frequently; always confirm current rules with local authorities.
What type of property performs best as an Airbnb in Chicago?+
In Chicago, the highest-performing STR properties are typically 1–2 bedroom apartments and condos near downtown. Guests in urban markets prioritize location, walkability, and modern amenities. The most efficient segment by revenue-per-dollar-invested is typically the 2-bedroom category.
What is the best season for Airbnb in Chicago?+
Chicago sees peak STR demand during spring (March–May) and fall (September–October). During peak season, top properties can command rates 15% above their annual average. Demand remains relatively stable throughout the year, with only moderate seasonal variation.
How much does it cost to buy an STR investment property in Chicago?+
The median home value in Chicago is approximately $385,000. With a 20% down payment, you'd invest roughly $89K in cash (including closing costs and setup). At the market-average revenue of $41,200/year, a property at median value would generate a gross revenue yield of approximately 10.7%. Use this calculator to model your specific purchase price, financing terms, and expense assumptions.
How does Chicago compare to other STR markets?+
Chicago offers accessible entry points relative to premium coastal markets. The $198 ADR is near the national STR average of roughly $185. For comparison, markets like Aspen and Malibu exceed $450 ADR but require significantly higher acquisition costs. Chicago offers a lower barrier to entry with reliable occupancy fundamentals.
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