Chicago, Illinois Short-Term Rental Market
Chicago STRs averaged $184/night at 62.8% occupancy in April 2026 across 16,354 active listings.
Quick Answer: Chicago, Illinois is an active short-term rental market. average occupancy in the Chicago market area is 70%. average monthly revenue in the Chicago market area is $4,873. average daily rate in the Chicago market area is $246. the top operator in the Chicago market area is Blueground with 687 listings. market score is 71/100 (grade B).
Market data reflects the wider Chicago market, which covers 24 areas. Regulations, taxes, and permit details below are specific to Chicago.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
Chicago is one of the largest short-term rental markets in the United States, with approximately 16,354 active listings as of April 2026. The market posted an average daily rate (ADR) of $184.32 and an occupancy rate of 62.8% in the most recent data month, yielding a RevPAR of $115.66. Revenue per listing averaged $3,159 per month.
On a year-over-year basis, occupancy improved 3.4 percentage points while ADR held essentially flat (up 0.15%), and monthly revenue grew 5.9%. The revenue growth outpacing ADR growth reflects the occupancy-driven improvement rather than rate inflation.
The listing mix skews heavily toward entire-place units, which account for 13,137 of the 16,354 active listings (80.4%). Private rooms make up 3,231 listings (19.8%), and shared rooms represent just 37. By bedroom count, studios and one-bedrooms are the largest segment at 6,932 listings, followed by two-bedrooms (4,281), three-bedrooms (3,004), four-bedrooms (1,410), and five-bedroom-plus properties (727). Airbnb is the dominant channel, with 9,843 Airbnb-only listings, 5,761 properties dual-listed on both platforms, and 801 VRBO-only listings.
Chicago’s market score of 71.1 out of 100 is anchored by an exceptionally strong rental demand score of 84.9, driven by the city’s 55.3 million annual visitors and dense convention and leisure infrastructure.
Seasonal Patterns
| Month | Occupancy |
|---|---|
| Jan | 48% |
| Feb | 56% |
| Mar | 62% |
| Apr | 61% |
| May | 69% |
| Jun | 73% |
| Jul | 72% |
| Aug | 68% |
| Sep | 66% |
| Oct | 64% |
| Nov | 56% |
| Dec | 55% |
Month-by-month nightly rates and revenue figures for Chicago are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Top Short-Term Rental Operators in Chicago market area
Ranked by total active listings. Useful for understanding the competitive landscape. Operator data is published for the Chicago market as a whole, which includes Chicago, so these counts are not Chicago-only figures.
| # | Operator | Listings | Reviews | Rating |
|---|---|---|---|---|
| 1 | Blueground | 687 | 290 | ★ 4.40 |
| 2 | Luxury Lili Stays | 189 | 9,757 | ★ 4.64 |
| 3 | Kasa Properties | 156 | 7,826 | ★ 4.71 |
| 4 | Slumber Stay | 137 | 7,814 | ★ 4.53 |
| 5 | Evolve | 127 | 2,763 | ★ 4.36 |
What Kind of STR Should I Buy in Chicago?
Revenue and nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Chicago are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 60% |
| vrbo | 4.9% |
| both | 35.1% |
Home Value Trends (Chicago)
Typical home values, median sale prices, and the 10-year price trend for Chicago are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Insights
Booking-window and length-of-stay analysis for Chicago — how far ahead guests book and how to price around it — is available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Short-Term Rental Regulations
Chicago permits short-term rentals but operates one of the most structured regulatory frameworks of any major U.S. city. Every STR unit must obtain an annual Shared Housing Unit registration number at a cost of $250 per year. Hosts operating more than one unit must also hold a Shared Housing Unit Operator License (SHUOL). Properties with 2 to 11 sleeping rooms serving breakfast require a Bed and Breakfast license.
A primary residence requirement applies to single-family and 2-4 unit buildings: the host must occupy the property at least 245 days per year. Buildings with 5 or more units are exempt from the primary-residence rule but face a per-building cap limiting STR units to one-quarter of total dwelling units or 6 units, whichever is less. Every address is screened against the Chicago Zoning Ordinance and a prohibited buildings list that includes more than 2,300 ineligible addresses. Hosts must carry at least $1,000,000 in commercial general liability insurance naming the City as an additional insured.
The tax burden is substantial. The city layers a 4.5% Hotel Accommodations Tax, a 4% Shared Housing Surcharge, and a 2% Domestic Violence Surcharge, producing a 10.5% combined city rate. With Cook County and Illinois state taxes, the composite rate reaches approximately 27.75%, the highest STR tax burden of any major U.S. tourism destination. Enforcement is rated strict, with fines ranging from $1,500 to $3,000 per day for operating without registration and up to $10,000 plus potential criminal charges for false primary-residence declarations. Chicago continues to add properties to its prohibited buildings list and enforces rules through platform data-sharing agreements.
Market Comparison
Chicago’s April 2026 occupancy of 62.8% exceeds the U.S. STR market median of approximately 55%, positioning it as an above-average demand market. Its ADR of $184.32 is below the approximate U.S. median of $220, reflecting Chicago’s large apartment-heavy inventory which pulls the average down relative to resort or beach markets with higher-end unit mixes.
The market’s rental demand score of 84.9 out of 100 is a standout metric, ranking it among the top demand markets nationally due to the city’s convention infrastructure, 55.3 million annual visitors, and dense population of 2.7 million. The total market score of 71.1 is moderated primarily by regulatory complexity (score 67.6) and seasonality (score 65.3), both of which represent real operational risks.
Professional management presence is significant. Blueground leads with 687 listings (4.2% of total active inventory), followed by Luxury Lili Stays at 189 listings and Kasa Properties at 156 listings. The top 5 operators collectively manage 1,296 listings, representing approximately 7.9% of the market. The remaining 92% of inventory is managed by individual hosts or smaller operators, a sign that the market is not yet heavily consolidated.
Frequently Asked Questions About Chicago, Illinois
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