Is Highland Park, Illinois Good for Airbnb Investment?

To start an Airbnb in Highland Park, Illinois, begin by researching local zoning ordinances as Highland Park requires short-term rental properties to comply with residential zoning laws and obtain a business license from the City Clerk's office, which typically costs around $50-100 annually. Contact the Highland Park Building Department to determine if you need additional permits, as properties may require inspections for fire safety and occupancy limits, with fees ranging from $100-300. Find a suitable property in residential zones that allow short-term rentals, ensuring it meets the city's requirements for parking, noise ordinances, and neighbor notification procedures that Highland Park implemented around 2018-2019. Purchase comprehensive furnishings including quality bedding, kitchen essentials, WiFi, and safety equipment like smoke detectors and fire extinguishers, budgeting approximately $5,000-15,000 for a complete setup. Create your Airbnb listing with professional photos, competitive pricing research showing Highland Park properties typically rent for $80-200 per night depending on size and location, and detailed descriptions highlighting proximity to Lake Michigan and Chicago. For ongoing management, establish check-in procedures, maintain regular cleaning schedules, respond promptly to guest communications, collect and remit Illinois state sales tax (currently 6.25%) plus local Highland Park hotel taxes (estimated 3-5%), and ensure compliance with noise restrictions and occupancy limits that Highland Park enforces to maintain neighborhood character.

Highland Park, Illinois offers strong STR potential due to its proximity to Chicago (30 miles north), affluent demographics, and Lake Michigan access, making it attractive for business travelers and weekend getaways. Target properties within walking distance of downtown Highland Park, near Ravinia Festival venue (major summer draw), or close to the lakefront and beaches, with 2-4 bedroom single-family homes or condos featuring modern amenities, parking, and outdoor spaces performing best. Analyze comparable nightly rates using AirDNA and Mashvisor, which show Highland Park averaging $150-250/night depending on season and proximity to Ravinia, with summer months (June-August) commanding premium pricing during festival season. Research competition through Airbnb and VRBO searches, noting that properties near Ravinia Park and downtown perform strongest, while monitoring occupancy rates of 60-75% annually with higher summer demand. Utilize tools like AirDNA for market analytics, Mashvisor for investment analysis, and local resources including Highland Park Chamber of Commerce for event calendars, while partnering with local property management companies like Awning or RedAwning who understand municipal regulations, as Highland Park requires STR licensing and has specific zoning restrictions that favor owner-occupied properties or designated rental zones.

To obtain an Airbnb/STR permit in Highland Park, Illinois, you must first contact the City of Highland Park Community Development Department at City Hall located at 1707 St. Johns Avenue to apply for a Short-Term Rental License. Required documents typically include a completed application form, proof of property ownership or lease agreement, certificate of insurance with minimum $1 million liability coverage, floor plan of the rental unit, contact information for a local responsible party available 24/7, and proof of compliance with fire safety codes including smoke and carbon monoxide detectors. The application fee is estimated at $200-300 annually with potential additional inspection fees of $100-150. You must also register with the Illinois Department of Revenue for tax collection purposes and obtain a business license from Highland Park if operating as a business entity. The property must comply with zoning regulations (typically restricted in certain residential zones), maintain occupancy limits based on bedrooms and square footage, provide adequate parking spaces, and ensure the property meets all building and safety codes. The approval timeline is generally 30-60 days depending on inspection scheduling and document completeness. Highland Park specifically requires STR operators to maintain a guest registry, post emergency contact information prominently in the rental unit, limit noise levels especially during evening hours, and ensure compliance with the city's rental property maintenance standards including regular inspections.

Short-term rentals (STRs) are currently prohibited in Highland Park, Illinois. The city enacted a comprehensive ban on STRs in 2019 following concerns about housing availability, neighborhood character, and parking issues. Highland Park's municipal code specifically prohibits the rental of residential properties for periods of less than 30 consecutive days, with limited exceptions for certain zoned areas. The ordinance applies citywide across all residential districts, including single-family homes, condominiums, and apartments. Violations can result in fines up to $1,000 per day, and the city actively enforces these regulations through complaint-driven investigations. Unlike some neighboring communities that have opted for licensing and regulation systems, Highland Park chose an outright prohibition approach, citing the need to preserve residential neighborhoods and maintain adequate long-term housing stock for residents. The ban remains in effect as of 2024, with no recent legislative changes to allow STRs, making Highland Park one of the more restrictive municipalities in the Chicago metropolitan area regarding short-term rental accommodations.

Highland Park's most attractive Airbnb investment areas include the downtown district near the Ravinia Festival grounds, which draws over 600,000 visitors annually for summer concerts and events, creating consistent seasonal demand from May through September. The lakefront neighborhoods along Sheridan Road offer premium rental potential due to proximity to Lake Michigan beaches and scenic views, attracting weekend tourists and summer vacationers willing to pay higher rates. The area near Highland Park Hospital and medical facilities generates steady business travel demand year-round from medical professionals, patients' families, and pharmaceutical representatives. The historic Port Clinton Square district appeals to visitors seeking walkable access to boutique shopping, restaurants, and the Metra train station providing easy Chicago access, making it ideal for both leisure and business travelers. The residential areas near Sunset Woods Park and the Nature Center attract families visiting for youth sports tournaments and outdoor activities, while the proximity to major corporations like Abbott Laboratories in nearby Lake Bluff creates consistent corporate housing demand for temporary relocations and extended business stays.

Highland Park, Illinois imposes a 3% municipal hotel/motel tax on short-term rental accommodations including Airbnb properties, which applies to stays of less than 30 consecutive days. This tax is collected directly from guests at the time of booking through Airbnb's automated tax collection system, which remits payments quarterly to the city on behalf of hosts. Additionally, Cook County levies a 2.75% accommodation tax that also applies to short-term rentals, bringing the total occupancy tax rate to approximately 5.75%. The Illinois state hotel operators' occupation tax of 6% may also apply depending on the specific classification of the rental. Hosts must register with the city and obtain a short-term rental license, and while Airbnb handles most tax collection automatically, hosts remain ultimately responsible for ensuring compliance and may need to file periodic reports with the city. There are generally no exemptions for stays under 30 days, though longer-term stays exceeding 30 consecutive days are typically exempt from occupancy taxes and instead subject to standard sales tax rates.

The total cost to start an Airbnb in Highland Park, Illinois is approximately $650,000-$750,000. Property purchase represents the largest expense at $550,000-$650,000 based on median home prices in this affluent North Shore suburb. Furnishing costs range from $25,000-$35,000 for quality furniture, bedding, kitchenware, and decor suitable for the upscale market. Initial setup including professional photography, listing creation, and marketing materials costs $2,000-$3,000. Permits and fees including business license, short-term rental permit, and potential HOA approvals total $1,500-$2,500. Insurance including landlord and short-term rental coverage adds $3,000-$4,000 annually. Utilities setup and deposits for electricity, gas, water, internet, and cable cost $1,000-$1,500. First six months operating costs including utilities ($1,200), cleaning services ($3,600), supplies and maintenance ($2,000), platform fees ($4,800 assuming 20% occupancy), and property management if outsourced ($7,200) total approximately $18,800. Additional considerations include potential property taxes of $15,000-$20,000 annually and marketing costs for initial bookings of $2,000-$3,000.

Highland Park, Illinois Airbnb properties typically generate annual revenues between $25,000-$45,000 for entire homes and $12,000-$22,000 for private rooms, with occupancy rates averaging 65-75% due to the area's proximity to Chicago and Lake Michigan attractions. Operating expenses generally run 40-50% of gross revenue, including cleaning fees ($75-$125 per turnover), property management (15-25%), utilities ($200-$400 monthly), insurance ($1,200-$2,000 annually), and maintenance costs. Net profit margins typically range from 15-25% for well-managed properties, with higher-end homes near Ravinia Festival grounds commanding premium rates of $200-$350 per night during summer months compared to $120-$180 in off-season. Success factors include proximity to Metra train stations for Chicago commuters, professional photography showcasing the suburban charm, and targeting corporate travelers visiting nearby Abbott Laboratories or Baxter International headquarters. Properties within walking distance of downtown Highland Park or the lakefront consistently outperform those in residential areas by 20-30% in both occupancy and nightly rates, with some hosts reporting annual profits of $8,000-$15,000 after all expenses on properties valued between $400,000-$700,000.

Highland Park, Illinois Airbnb investments typically generate annual ROI of 8-12% with cash-on-cash returns ranging from 6-10% based on current market conditions. Properties in desirable neighborhoods near Lake Michigan and downtown Highland Park command average daily rates of $150-250, with occupancy rates of 65-75% annually. Initial investment recovery and profitability generally occurs within 18-24 months, assuming 20-25% down payment on properties valued between $400,000-700,000. The market benefits from proximity to Chicago (30 miles north), strong tourism demand from North Shore attractions, and corporate travelers visiting companies like Abbott Laboratories and Baxter International. Seasonal variations show peak performance May through October with 15-20% higher rates, while winter months see 20-30% occupancy drops. Operating expenses typically consume 35-45% of gross rental income including property management, cleaning, utilities, and maintenance, leaving net yields of 7-9% for well-managed properties in prime locations within 2-3 blocks of Metra stations or lakefront areas.

STRSearch is a national platform that specializes in identifying profitable short-term rental properties for investors looking in Highland Park, Illinois. Local real estate agents who focus on investment properties in the Highland Park area include Coldwell Banker Realty agents specializing in North Shore properties, Berkshire Hathaway HomeServices Chicago agents with vacation rental expertise, and @properties agents who understand the Lake County short-term rental market. Awning offers nationwide Airbnb property investment services and can help identify properties in Highland Park's desirable North Shore location. Mashvisor provides data analytics for short-term rental investments and covers the Highland Park market with rental yield projections. Local property management companies like RedAwning and Vacasa can assist with both property acquisition advice and subsequent management of Highland Park Airbnb properties. AirDNA offers market analysis specifically for Highland Park's short-term rental performance, while BiggerPockets connects investors with local Highland Park real estate professionals experienced in vacation rental investments. Roofstock and Arrived Homes are national platforms that occasionally feature Highland Park area properties suitable for Airbnb conversion, and local mortgage brokers like First Midwest Bank can provide specialized financing for investment properties intended for short-term rental use in Highland Park's premium North Shore market.