Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Chicago, Illinois
In Chicago, Illinois, Airbnb offers a diverse range of accommodations to suit various preferences and budgets. Guests can choose from stylish downtown apartments with stunning skyline views, perfect for those wanting to be in the heart of the city. For a more local experience, charming brownstones and historic greystones in neighborhoods like Lincoln Park and Wicker Park provide a cozy, residential feel. Travelers seeking luxury can find high-end penthouses and modern lofts with upscale amenities. Additionally, budget-conscious visitors might opt for private rooms in shared homes or quaint studios. Unique stays, such as houseboats on Lake Michigan or artistically themed spaces, add an extra layer of intrigue for those looking for something different. Overall, Chicago's Airbnb offerings cater to a wide array of tastes, ensuring a memorable stay in the Windy City.
In Chicago, Illinois, Airbnb rentals are regulated under the Shared Housing Ordinance. Hosts are required to register their property with the city and obtain a Shared Housing Unit Registration number. The ordinance limits the number of units that can be rented in a building and imposes a cap on the number of nights a unit can be rented per year if the host is not present. Additionally, hosts must adhere to specific health and safety standards. Chicago imposes a 4.5% Shared Housing Surcharge on the gross rental or leasing charge, which is in addition to the standard hotel accommodation tax. These regulations aim to balance the interests of residents, property owners, and visitors while ensuring safety and compliance with local laws.
Managing an Airbnb in Chicago, Illinois, involves several key tasks to ensure a successful operation. Hosts need to maintain compliance with local regulations, including obtaining the necessary licenses and adhering to zoning laws specific to short-term rentals. Effective property management includes regular cleaning, maintenance, and restocking of essentials to provide a welcoming environment for guests. Pricing strategies should be adjusted based on market trends and seasonal demand to maximize occupancy and revenue. Additionally, hosts must focus on guest communication, providing timely responses to inquiries and ensuring a smooth check-in and check-out process. Marketing the property through appealing listings and leveraging positive reviews is also crucial to stand out in Chicago's competitive Airbnb market.
When visiting Chicago, Illinois, some of the best areas to stay in an Airbnb include the vibrant neighborhood of Wicker Park, known for its eclectic mix of boutiques, cafes, and nightlife, offering a trendy and artistic vibe. The Loop is ideal for those wanting to be in the heart of the city, close to iconic attractions like Millennium Park and the Art Institute of Chicago. Lincoln Park offers a more relaxed atmosphere with its beautiful parks, the Lincoln Park Zoo, and proximity to Lake Michigan. For a luxurious experience, consider the Gold Coast, which boasts historic mansions, upscale shopping, and fine dining. Lastly, the West Loop is perfect for food enthusiasts, with its renowned restaurant scene and proximity to downtown. Each of these neighborhoods provides a unique experience, catering to different interests and preferences.
Chicago, Illinois, presents a dynamic Airbnb investment landscape, characterized by its diverse neighborhoods and robust tourism industry. The city's vibrant cultural scene, iconic architecture, and renowned culinary offerings attract a steady stream of visitors year-round. Neighborhoods like River North, known for its nightlife and proximity to downtown attractions, and Lincoln Park, with its family-friendly atmosphere and access to green spaces, are particularly appealing for short-term rentals. The West Loop, with its trendy restaurants and burgeoning tech scene, also offers promising returns. However, investors should be mindful of Chicago's stringent short-term rental regulations, which require careful compliance to ensure a successful venture. Overall, Chicago's blend of cultural richness and economic vitality makes it a compelling market for Airbnb investments.
As of the latest data, the average Airbnb revenue in Chicago, Illinois, varies significantly depending on factors such as location, property type, and seasonality. Generally, hosts in popular neighborhoods like the Loop, River North, and Lincoln Park tend to earn higher revenues due to increased demand from tourists and business travelers. On average, a well-located and well-maintained property can generate monthly revenues ranging from $2,000 to $4,000, with peak earnings during the summer months and major city events. However, these figures can fluctuate based on occupancy rates, pricing strategies, and competition within the market. Hosts who offer unique experiences or amenities may also see higher returns.
The occupancy rate for Airbnbs in Chicago, Illinois, typically fluctuates with the city's distinct seasons. During the peak summer months, from June to August, occupancy rates are generally higher due to the influx of tourists attracted by the city's numerous festivals, outdoor events, and favorable weather. This period often sees occupancy rates reaching upwards of 70-80%. In contrast, the winter months, particularly January and February, experience a dip in occupancy, often falling to around 40-50%, as the colder weather and fewer events lead to decreased demand. Spring and fall serve as transitional periods with moderate occupancy rates, as visitors come for events like the Chicago Marathon in October or the St. Patrick's Day celebrations in March. Overall, Chicago's Airbnb market is characterized by a strong summer season and a quieter winter, with spring and fall offering balanced occupancy levels.
Why Choose Checkmate Rentals?
Other Property Managers | ||
---|---|---|
Cost | Starting at 15% fee | 25-40% fee |
Guest Communications | Guest response within 10 minutes, 24 hours a day | Sporadic guest communications |
Host Communications | Designated host call in phone line | Bot response assistants |
Insurance | Full damage protection for every reservation | Unreliable insurance coverage |
Contract | No annual agreements | Contract lock-ins |
What you get with Checkmate Rentals
Attract Guests

Listing on all top booking sites
Targeted digital marketing
High-definition photography
Custom copywriting
Manage Details

Dynamic rate-setting technology
Dedicated reservation agents
24/7 guest service
Consistent, professional cleaning
Stocking guest amenities
Payment processing
Take Care of You

Unlimited owner holds
No fixed contracts
Local staff in every market
Inspections and regular maintenance
Guest screening
Optional short-term rental insurance
Get in touch with us.
Checkmate Rentals is a full-service property manager. That means the Airbnb listing, the home, the guest and the work is our responsibility.
Local Team Support
Know that you have a friendly, accessible team right up the road to handle any property needs.
Guest Screenings
Book only the most qualified guests 25 and over who’ll enjoy your home the right way.
Unlimited Owner Use
Block off your vacation days with ease, and enjoy your home as often as you want.
Reliable Property Maintenance
Keep your home running smoothly around the clock with a fast, reliable maintenance team.
Transparent Finances
Transparent Finances Booking payouts get paid directly to you for full financial transparency. We never handle your money.
Fast 24/7 Guest Communication
Make every guest feel cared for with industry best response times of 1-15 minutes day and night.
Marketing
Target, attract & book qualified guests with photography, email marketing, and optimized listings.
Revenue Management
Get the competitive edge with dynamic pricing and rates optimized daily by your pricing manager.
Direct Bookings
Earn more year after year as guests book their stay directly on our website.
Housekeeping
Make the perfect first impression with wall-to-wall cleanings before guests arrive.
Inspections
Know your property is guest-ready is top-to-bottom inspections after every booking.
Guest Damage Coverage
Save more when you let us cover accidental guest damage coverage up to $3k.
Smart Home Management
We manage your digital locks & noise monitoring tech in your home.
Fast Listings
Get your home fully listed and ready for guests in as little as 3 days.
Automated Touchpoints
Give guests a seamless experience with automated touchpoints from booking to checkout.
Owner Portal
Stay in the loop on your property with our easy-to-use owner portal that lets you check everything you need.
