Is Chicago, Illinois Good for Airbnb Investment?

Get significant tax savings and earn cash flow by investing in a short-term rental with data-backed selection. No guessing!

Find Your Airbnb Investment
Chicago, Illinois market research

Chicago, Illinois Airbnb Investment Overview

$2,500–$4,200Typical monthly host earnings
8–12%Typical annual ROI
65–70%Average annual occupancy
VariesCombined taxes and local fees
Investment

Is Airbnb a Good Investment in Chicago, Illinois?

Potentially—Chicago, Illinois combines visitor demand with long-term real estate upside.

  • Presents a complex yet potentially rewarding opportunity.
  • The city's robust tourism sector, driven by its iconic architecture, diverse culinary scene, and numerous cultural attractions, consistently draws millions of visitors.
  • Current market conditions in Chicago indicate a competitive landscape, with property values showing moderate growth.
  • However, the investment potential is influenced by the city's specific short-term rental regulations, which can impact profitability and operational ease.
  • Thorough research into hyper-local market dynamics, including neighborhood-specific occupancy rates and average daily rates.
Earnings

How Much Does an Average Airbnb Earn in Chicago?

$2,500–$4,200 per month based on location, season, and property quality.

  • Airbnb hosts in Chicago typically earn between $2,500 to $4,200 per month, with downtown and Near North Side properties commanding the highest rates averaging $150-250 per night.
  • Seasonal variations show peak earnings during summer months when revenue can increase by 25-40% due to tourism and favorable weather.
  • Key factors affecting earnings include proximity to major attractions like Millennium Park and Navy Pier, property type (entire homes outperform private rooms by 60-80%), neighborhood safety ratings.
  • Properties near public transportation, particularly the L train system, consistently achieve 10-15% higher occupancy rates.
ROI Analysis

Airbnb Return on Investment in Chicago

Potentially strong—typical annual ROI is 8–12%.

  • Airbnb investments in Chicago typically generate an average ROI of 8-12% annually, with properties in popular neighborhoods like Lincoln Park, Wicker Park.
  • The average payback period for initial investment ranges from 7-10 years, depending on property acquisition costs and renovation expenses.
  • Chicago's Airbnb market shows occupancy rates averaging 65-75% with daily rates between $120-180 for one-bedroom units and $200-300 for larger properties.
  • Compared to traditional long-term rentals in Chicago, which typically yield 6-8% ROI, short-term rentals can provide 2-4 percentage points higher returns.
  • Properties within 2 miles of downtown Chicago and major attractions like Millennium Park tend to outperform suburban locations by 15-25% in terms of revenue generation.
Occupancy Rate

Average Airbnb Occupancy Rate in Chicago

Chicago, Illinois averages 65–70% annual occupancy, with seasonal variation.

  • Chicago's Airbnb occupancy rates average approximately 65-70% annually, with significant seasonal variations that peak during summer months (June-August) at 75-80% due to favorable weather, festivals.
  • Spring and fall maintain moderate occupancy rates around 65-70%, with notable spikes during major events like Lollapalooza, Chicago Marathon, and convention season.
  • Chicago's occupancy rates generally align closely with Illinois state averages of 66-68% but fall slightly below national Airbnb averages of 70-72%.
  • The city's occupancy performance is strongest in neighborhoods like Lincoln Park, Wicker Park, and downtown areas near major attractions.
Best Neighborhoods

Best Neighborhoods for Airbnb in Chicago

The strongest opportunities balance visitor demand, nightly rates, and acquisition cost.

  • The best Airbnb investment neighborhoods in Chicago include Lincoln Park, which offers strong rental demand due to its proximity to DePaul University, Lincoln Park Zoo, and lakefront attractions.
  • River North stands out as the premier downtown location with easy access to Magnificent Mile shopping, restaurants, and corporate offices.
  • Wicker Park attracts younger demographics and creative professionals with its vibrant nightlife, trendy restaurants, and music venues.
  • The Loop provides excellent investment potential due to its central business district location, proximity to major hotels and convention centers, and easy public transportation access.
  • Old Town combines historic charm with tourist appeal, featuring proximity to Second City comedy club and upscale dining, attracting both leisure and business guests.
  • West Loop has emerged as a hot neighborhood with its restaurant scene and proximity to Google's offices and Union Station, drawing tech workers and food enthusiasts.
  • Logan Square offers more affordable entry points while maintaining strong rental potential through its hip.
Regulations

Short-term Rental Regulations in Chicago

Yes, but only where zoning permits short-term rentals and every required license is current.

  • Chicago requires short-term rental operators to obtain a Shared Housing Unit license through the city's Department of Business Affairs and Consumer Protection.
  • Properties must be owner-occupied primary residences, meaning hosts can only rent out their main home where they live at least 185 days per year.
  • Short-term rentals are prohibited in buildings with 3 or more units unless the entire building is owner-occupied.
  • The registration process requires submitting proof of residency, property ownership or lease agreements, liability insurance of at least $500,000, and passing safety inspections that check smoke detectors.
  • Recent changes implemented in 2021 strengthened enforcement mechanisms, increased penalties for violations up to $1,500 per day, required platforms like Airbnb to verify host licenses before listing properties.
Fees and Taxes

Short-term Rental Fees and Taxes in Chicago

Tax rates vary by jurisdiction; licensing, inspection, and insurance costs are additional.

  • Short-term rentals in Chicago, Illinois are subject to multiple fees and taxes including a 4.5% city hotel tax, 1% state hotel tax, and 10.25% combined sales tax.
  • Property owners must pay a $250 annual shared housing registration fee to the city, plus a $60 business license fee.
  • Tourism taxes include the Metropolitan Pier and Exposition Authority tax of 2.5% for downtown properties and 1% for other areas.
  • Additional costs include a $100 initial inspection fee, potential $150 re-inspection fees if violations are found, and a $25 late renewal penalty.
  • Properties in certain zones may require special use permits costing $1,685 plus legal notice fees of approximately $300.
  • Hosts must also maintain liability insurance with minimum coverage requirements, typically costing $200-500 annually.
Common questions

Chicago, Illinois Airbnb investment FAQs

How to start an Airbnb in Chicago, Illinois?

To start an Airbnb in Chicago, Illinois, you must first research the city's strict short term rental regulations, which require hosts to register with the Chicago Department of Business Affairs and Consumer Protection and obtain a Short Term Residential Rental License, costing approximately $250 annually.

Launch checklist

  • Next, secure the necessary permits including a business license ($75 to $300 depending on property type) and ensure compliance with Chicago's zoning laws, fire safety requirements, and building codes.
  • Find a suitable property in permitted zones (primarily residential areas, avoiding certain downtown districts where short term rentals are prohibited), considering proximity to attractions like Millennium Park, Navy Pier, or Wicker Park.
  • Furnish the space with quality basics including comfortable bedding, kitchen essentials, WiFi, TV, and Chicago specific amenities like winter gear storage and local guidebooks, budgeting $3,000 to $8,000 for a one bedroom setup.
  • Create your listing on Airbnb with professional photos highlighting Chicago skyline views or neighborhood character, competitive pricing ($80 to $200+ per night depending on location and season).
  • Finally, manage your property by maintaining consistent communication with guests, coordinating cleaning between stays (budget $50 to $100 per turnover), staying updated on Chicago's evolving regulations.
What's the best way to identify good STR properties in Chicago, Illinois?

To identify profitable short term rental properties in Chicago, Illinois, focus on neighborhoods like Lincoln Park, Wicker Park, River North, and areas near major attractions such as Millennium Park, Navy Pier, and the Loop, prioritizing locations within walking distance of public transportation, restaurants.

What to prioritize

  • Target properties with 2 to 3 bedrooms, modern amenities, parking availability, and unique architectural features like exposed brick or city views that photograph well for listings.
  • Conduct pricing analysis using AirDNA and Mashvisor to evaluate average daily rates ($100 to 300+ depending on location and season), occupancy rates (typically 60 to 75% in prime areas), and seasonal demand patterns.
  • Research competition by analyzing similar properties within a 0.5 mile radius using tools like AllTheRooms and STR Helper, examining their pricing strategies, amenities, and guest reviews to identify market gaps.
  • Utilize Chicago specific resources including the city's STR registration requirements, local property management companies like RedAwning or Vacasa, and neighborhood specific Facebook groups.
How to get an Airbnb permit in Chicago, Illinois?

To obtain an Airbnb/STR permit in Chicago, Illinois, you must first register with the City of Chicago's Department of Business Affairs and Consumer Protection (BACP) by visiting their online portal at chicago.gov or applying in person at City Hall (121 N LaSalle St).

Documents and approvals

  • Required documents include a completed short term rental registration application, proof of property ownership or lease agreement with landlord consent, certificate of insurance with minimum $500,000 liability coverage, floor plan of the rental unit.
  • Chicago specific requirements mandate that hosts must be present during guest stays (shared home rentals) or live within 2 miles of the property (vacation rentals), limit rentals to maximum 4 guests, maintain guest registry, post emergency contact information.
  • The application process typically takes 4 to 6 weeks for approval, and you must also obtain a business license ($75 to $125 depending on property type) and remit the city's 4.5% hotel tax on all bookings.
  • Properties in buildings with 6+ units require additional condominium association or building owner approval, and all rentals must pass safety inspections and comply with Chicago's noise ordinances and parking regulations.
Is it legal to operate a short-term rental in Chicago, Illinois?

Short term rentals (STRs) are legal in Chicago, Illinois, but operate under strict regulations implemented in 2016 and updated in 2021. The city requires STR operators to obtain a license, pay registration fees, and comply with zoning restrictions that limit STRs primarily to residential areas while prohibiting them in certain downtown zones and near airports.

Core operating requirements

  • Chicago caps the number of STR licenses citywide and restricts operators to hosting no more than 120 days per year unless they live on site, with additional requirements including liability insurance, safety equipment, and neighbor notification procedures.
  • The regulations were strengthened following concerns about housing availability and neighborhood impacts, with the city implementing a tiered system that distinguishes between hosted rentals (where owners are present) and non hosted rentals (entire units).
What are the best places to invest in Airbnb in Chicago, Illinois?

The best Airbnb investment neighborhoods in Chicago include Lincoln Park, which attracts tourists with its proximity to Lincoln Park Zoo, beaches, and vibrant nightlife while serving business travelers heading to downtown offices.

Areas to research

  • The Loop offers excellent potential due to its central business district location, hosting major corporate headquarters like Boeing and serving convention attendees at McCormick Place.
  • Wicker Park and Bucktown appeal to younger travelers seeking trendy restaurants, boutique shopping, and Chicago's famous music scene.
  • Near North Side, particularly around River North and Streeterville, benefits from proximity to Navy Pier (attracting 8+ million annual visitors), Magnificent Mile shopping, and numerous hotels that create spillover demand.
  • Lakeview, especially near Wrigleyville, capitalizes on Cubs games at Wrigley Field and summer festival season, while also attracting LGBTQ+ travelers to the Boystown area.
  • West Loop has emerged as a hot investment area due to its restaurant scene, proximity to United Center for Bulls and Blackhawks games, and growing residential development.
  • Old Town provides steady demand from tourists visiting Second City comedy club and families attending Lincoln Park Zoo, while maintaining easy access to downtown business districts.
Airbnb and lodging taxes in Chicago, Illinois

In Chicago, Illinois, Airbnb hosts must collect and remit multiple lodging taxes including the Chicago Hotel Accommodations Tax at 4.5%, the Metropolitan Pier and Exposition Authority (MPEA) tax at 2.5%, and the Illinois Hotel Operators' Occupation Tax at 6% of gross rental receipts. Additionally, Chicago imposes a Short Term Rental Tax of $4 per night per unit.

Taxes and filing responsibilities

  • These taxes apply to stays of less than 30 consecutive days and are collected from guests at the time of booking, with Airbnb typically handling collection and remittance directly to the city and state on behalf of hosts through their automated tax collection service that began around 2017 to 2018.
  • Hosts must register with the Chicago Department of Business Affairs and Consumer Protection and obtain a short term rental license, and while there are limited exemptions for stays over 30 days or certain medical related accommodations.
Total cost to purchase, furnish and operate an Airbnb in Chicago, Illinois

Starting an Airbnb in Chicago, Illinois requires approximately $380,000 to $420,000 in total initial investment.

Cost breakdown

  • Property purchase costs average $350,000 for a median priced 2 bedroom condo suitable for short term rentals in desirable neighborhoods like Lincoln Park or Wicker Park.
  • Furnishing costs range $15,000 to $25,000 including furniture, appliances, linens, and décor to create an attractive guest experience.
  • Initial setup expenses total $3,000 to $5,000 covering professional photography, listing creation, smart locks, and technology upgrades.
  • Chicago requires a short term rental license ($250 annually) plus business license ($75), with potential additional fees for inspections totaling $500 to $800.
  • Insurance costs $2,000 to $3,500 annually for specialized short term rental coverage beyond standard homeowner's insurance.
  • Utility setup and deposits average $500 to $800 for electricity, gas, water, internet, and cable services.
  • First six months operating costs including utilities ($1,200), cleaning services ($2,400), supplies and maintenance ($1,500), platform fees to Airbnb and VRBO ($3,000 estimated), marketing ($800).
Are Airbnb properties in Chicago, Illinois profitable?

Airbnb properties in Chicago, Illinois demonstrate mixed profitability with average annual revenues ranging from $25,000 to $45,000 for typical 1 to 2 bedroom units, while expenses including mortgage, utilities, cleaning, maintenance, and Airbnb fees typically consume 60 to 75% of gross revenue. Properties in prime neighborhoods like Lincoln Park, Wicker Park, and Near North Side command premium rates of $150 to 250 per night with 65 to 75% occupancy rates, while properties in outer neighborhoods average $80 to 120 per night with 50 to 60% occupancy.

Profitability indicators

  • Success factors include strategic location within 2 to 3 miles of downtown, professional photography, consistent 4.8+ star ratings, rapid guest communication.
  • A case study of a Lincoln Park 2 bedroom condo purchased for $350,000 in 2019 generated $38,000 in annual Airbnb revenue against $28,000 in total expenses (including $18,000 mortgage, $4,000 utilities, $3,000 cleaning, $2,000 maintenance, $1,000 platform fees).
What is the expected return on investment for an Airbnb in Chicago, Illinois?

Airbnb investments in Chicago, Illinois typically generate annual ROI between 8 to 15% depending on property location and management efficiency. Cash on cash returns generally range from 12 to 22% annually, with investors seeing stronger performance in properties within 2 to 3 miles of major attractions like Millennium Park, Navy Pier, and the Loop business district.

Return planning figures

  • Most well positioned Chicago Airbnb investments reach profitability within 18 to 24 months, factoring in acquisition costs, renovation expenses averaging $15,000 to 30,000 per unit.
  • Properties in emerging neighborhoods like Pilsen and Logan Square show potential for 20 to 25% annual returns due to lower acquisition costs ($200,000 to 350,000) combined with growing tourism demand.
What company can help me find and buy a profitable Airbnb in Chicago, Illinois?

STRSearch is a national platform that specializes in identifying profitable short term rental properties for investors in Chicago, Illinois.

Companies and resources

  • Local Chicago based services include RedfinNow and Compass Real Estate which have dedicated investment property divisions, while @properties and Coldwell Banker have agents specializing in Airbnb investment properties.
  • National companies serving the Chicago market include Roofstock, which expanded into short term rental investments in 2021, BiggerPockets marketplace, and Mashvisor analytics platform.
  • Local Chicago real estate agents like those at Keller Williams Lincoln Park and RE/MAX Properties have developed expertise in Airbnb investment properties since 2019.
  • Additional services include AirDNA for market analysis, Awning property management and acquisition services, and local firms like Chicago Property Investors Group and Windy City Real Estate Investors which have been active in the STR market since 2020.
  • National platforms like Arrived Homes and Fundrise have also begun offering Chicago Airbnb investment opportunities, while local property management companies such as RedAwning and Vacasa provide end to end acquisition and management services for investors seeking profitable short term rental properties in Chicago's diverse neighborhoods.

How Smart Investors Build Wealth

Through Data-Driven STRs (Real Results)

From first-time investors to seasoned pros, see how our commitment to comprehensive data analysis led to unparalleled investment victories.

Smiling woman with dark hair and white blouse next to text reading 'Spot on $120K revenue prediction!' attributed to Allison Kraft, STR Search Client on dark green background.

From zero real estate experience to a thriving short-term rental business, Allison locked in $120K in revenue her first year  and is now expanding with STR Search again. Proof that the right team can turn analysis paralysis into profitable action!

- Allison
Portrait of a man with short dark hair and earbuds, alongside the quote 'Cash flow positive since day one!' attributed to Arul, STR Search Client, on a dark green background.

Thanks to John's expert guidance, I made my first real estate and Airbnb investment a massive success, with consistent positive cash flow and an exceptional return on investment!

- Arul
Quote saying 'Bank said This is better than their underwriting team!' by Philip Mann, STR Search Client, beside a smiling man with a bald head and light beard on a dark green background.

John's training gave me the confidence to secure a loan on the spot and scale from one STR to three. His approach is a total game-changer!

- Philip

Why Choose STR Search?

Success Rate
Data Accuracy
Service Scope
Risk Mitigation
Expert Network
STR Search Logo
100% profitable track record
Proprietary filters, precise forecasts
End-to-end STR investment support
Only cash-flow-positive matches
Vetted realtors, lenders, designers included
Other Services
Inconsistent ROI, no guarantees
Generic metrics, inaccurate estimates
Partial services only
No profitability screening
Limited or no partner access
Success Rate
Data Accuracy
Service Scope
Risk Mitigation
Expert Network
STR Search Logo
Success Rate
100% profitable track record
Data Accuracy
Proprietary filters, precise forecasts
Service Scope
End-to-end STR investment support
Risk Mitigation
Only cash-flow-positive matches
Expert Network
Vetted realtors, lenders, designers included
Other Services
Success Rate
Inconsistent ROI, no guarantees
Data Accuracy
Generic metrics, inaccurate estimates
Service Scope
Partial services only
Risk Mitigation
No profitability screening
Expert Network
Limited or no partner access
275+
Properties Acquired
$90M+
Purchased
$20.24M+
Total Taxes Saved

Put your money to work & 
lower your tax bill

We’ve spent years analyzing what works so you don’t have to. Our job is to cut through bad data and help you make smart, profitable decisions backed by real numbers.

Schedule Your Free Call

Trusted by hundreds of 
successful investors

Generate $3-5K+ monthly cash flow with our proven property matching system.

Build long-term wealth through STRs with cash flow, equity, and bonus depreciation.

Skip 6-12 months of trial and error with our data-driven underwriting and market analysis

The Proof is in Our Track Record...

We have a 100% success rate across $90M+ in Real Estate

Out of the 275+ properties we've helped our clients buy every single one has been profitable.

You want more money. More time. More freedom. But may be stuck trading hours for dollars, and scaling your investment strategy feels out of reach.

While others are getting lost in analysis paralysis, you’ve got capital and drive to change your situation. Investors who choose the right STRs can generate $3–5K/month in cash flow, plus serious tax benefits and long-term wealth.

We’ve spent years obsessed with STR investing data so you don’t have to.

With our property match services, there’s no guesswork! Just profitable properties built to perform. With the right deal, your capital can buy more than returns. It can buy your freedom.

Buildings
Rabbu logoAirbnb logoAirdna logoPriceLabs logo
Rabbu logo
Airbnb logo
Airdna logo
PriceLabs logo

All The Ways We Can Help You

Free courses, services, and trainings, to help you maximize your earnings from AirBnb...

Get in touch with us.

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.

Put your money to work & 
lower your tax bill

We’ve spent years analyzing what works so you don’t have to. Our job is to cut through bad data and help you make smart, profitable decisions backed by real numbers.

Schedule Your Free Call