The Ultimate Guide to Protect+Comply with Chicago's Airbnb Regulations

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Keeping your short term rental compliant in Chicago is not an easy task. If you dig deep into the City archives, you’ll find a 38-page Ordinance governing all short-term rentals. You can find the Ordinance HERE

Before you venture into this market and begin to invest your time and money, here is a run-down of the Ordinance so you are clean and compliant with the City:

Property Types

  • Single Family Homes: If you own a single family home, the City of Chicago asks that the dwelling unit be designated as the applicant’s primary residence.

  • 2-4 Unit Buildings: If you own a building containing two to four units, the City of Chicago asks that the building be designated as the applicant’s primary residence and no more than one unit in the building be used as a vacation rental.

  • 5+ Unit Buildings: If the dwelling unit is located in a building containing five or more unit dwellings an attestation that: in no more than six dwelling units in the building or one-quarter of the total dwelling units in the building. whichever is less. are or will be used as vacation rentals or shared housing units. in any combination

Registration and Insurance:

If this is your first Airbnb, than you only have to register through the Airbnb website. Airbnb automatically helps you register for your license

If you are interested in putting more than 1 unit on the short-term rental market, a Shared Unit Operator License is needed ($250 - Good for 2 years). In order to get a Shared Unit Operator License, you must go through the BACP web portal and go through their 6 step process.


Homeowner's insurance + General commercial liability insurance no less than $1m = ~$500 / year. There are short-term rental insurance companies available, if needed.

Fire code

According to the Fire Code of Chicago, you may have no more than 1 person per 125 SF per dwelling unit.

Safety and Rules When Operating Your Shared Housing Unit

● Clean soap, linens, towels, dishes, and utensils must be provided

● Notification to police of illegal activity is required

● Contact name, license number, and evacuation diagram displaying means of egress must be displayed on all entrances/exits

When you register, what information is shared with the City?

1. The host’s name (this should be the primary resident, not a co-host or business);

2. The address of the unit being registered;

3. The contact information for the host or a local contact person, such as a co-host, including email address and phone number (if available);

4. Whether the unit being listed is a:

  • Single family home;

  • Unit in a multi-unit building; and

  • Whether the listing will make the entire dwelling unit available for rent or a room or portion of the dwelling unit available for rent.

5. Whether the unit being listed is the host’s primary residence. “Permanent occupancy” means occupancy on a daily or nightly basis, or any part thereof, for a period of 32 or more consecutive days. “Transient occupancy” means occupancy on a daily or nightly basis, or any part thereof, for a period of 31 or fewer consecutive days.

Shared Housing Units -Commissioner's Adjustments

(a) The commissioner is authorized to grant an adjustment to allow:

(1) the operation of a shared housing unit located in:

  • a single family home that is not the shared housing host's primary residence; or

  • (ii) a building containing two to four dwelling units, inclusive, where the dwelling unit is not the shared housing host's primary residence; or

  • (iii) in a building containing two to four dwelling units, inclusive, an increase in the number of dwelling units that may be used as shared housing units.

Such an adjustment may be approved only if, based on a review of relevant factors, the commissioner concludes that such an adjustment would eliminate an extraordinary burden on the applicant in light of unique or unusual circumstances and would not detrimentally impact the health, safety, or general welfare of surrounding property owners or the general public.

Factors which the commissioner may consider with regard to an application for a commissioner's adjustment include, by way of example and not limitation:

  1. the relevant geography

  2. the relevant population density

  3. the degree to which the sought adjustment varies from the prevailing limitations,

  4. the size of the relevant building and the number of units contemplated for the proposed use

  5. the legal nature and history of the applicant

  6. the measures the applicant proposes to implement to maintain quiet and security in conjunction with the use

  7. any extraordinary economic hardship to the applicant, due to special circumstances, that would result from a denial

  8. any police reports or other records of illegal activity or municipal code violations at the location

  9. whether the affected neighbors support or object to the proposed use.

(b) A person seeking an adjustment shall make a written submission to the commissioner, presenting all factors which the applicant believes to be relevant to whether an adjustment is appropriate. The applicant shall provide a copy of the written submission to the adjoining neighbors. The commissioner shall review the materials and make a written determination within 60 days, which shall set forth the factors used in arriving at the determination. During the 60-day review period, the commissioner shall notify the affected alderman and solicit a recommendation based on the alderman's analysis of relevant factors, and may seek additional information or supplementary proof from the applicant, and may also solicit information from the community.

If the commissioner denies the application for an adjustment, the applicant, within fourteen days of receiving the denial, may request a hearing from the commissioner. Upon receiving such a request, the commissioner shall schedule and conduct a hearing expeditiously. At the hearing the commissioner may receive written submissions witness testimony, argument and documents regarding the application. The commissioner shall, within thirty days of the conclusion of the hearing, render a decision, which shall constitute a final determination for purposes of judicial review.

May this serve as your outline when looking to invest your time and money into short-term rentals in Chicago. It does not pay to try to skirt the laws because penalties go from $1000-5000 per occurrence. Save yourself the headache and time, and consult with a local expert to make sure you are legal and compliant.

Maximize Your Airbnb Occupancy to Maximize Cash Flow

Maximizing your Airbnb occupancy rate requires a proactive strategy and constant attention to your guests and listings throughout the all seasonal period. Here are pro tips to help you get the most from your Airbnb business during peak season.

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Your Airbnb occupancy rate is one of the most important factors to determine whether or not your Airbnb business is successful. Essentially, increasing the number of bookings you receive, and filling in the calendar's gaps, virtually guarantees you more money.

However, maximizing your Airbnb occupancy rate during peak season needs proactive planning and 2-4 months of forethought. Often, there’s only a Season, in which the demand for your short-term rentals are higher. Here are some quick tips to help you get the most from your Airbnb business during peak season.

Weed Out Outdated Information

How do your photos look compared to the competition? Have you made changes to your house rules? If you haven’t updated these items on your listings, do it now.

To increase your Airbnb occupancy rate, it starts with creating 5-STAR listings. Errors such as missing information, typos, and outdated photos will only drive potential guests away. While you should never mislead guests about the accommodations, optimize your listings with keywords or emotional words to help to create interest and boost the number of bookings you receive.

You should also be aware of the fact you might receive more guests who are looking for accommodations for a group or want to book at the last minute. Cater to these guests by updating your listings to emphasize how easy it is to book at the last minute or the fact that you offer ample sleeping arrangements for groups.

Keep Your Listing+Calendar Updated

Updating your listings frequently is the best way to maximize your Airbnb occupancy rate during peak season. Frequent pricing updates ensure that your listing prices are priced competitively at all times. .

Finally, to maintain your listings and ensure that guests always have access to accurate information about their availability, update your calendar at least 1 to 2 times per day. By following these tips, your listings will stay on top of Airbnb’s rankings, helping you to stay ahead of the competition.

Instant Book = Higher SEO

If you haven’t already, enable Instant Book because it increases your listings SEO. The easier you make it for guests to book your property, the easier it will be for you to achieve maximum occupancy rates.

If you’re wondering why Instant Book is so effective, consider things from the guest’s perspective for a moment. As a guest, you want the booking process to be simple and fast. Any additional steps that make it harder to book a listing simply make you more likely to consider listings from other hosts.

Even if a property has gorgeous Lake views, it isn't worth it if working with the host is difficult. Turning on Instant Book means it's simple and easy for guests to book with you.

5-STAR REVIEWS + Audit Your Review Count

As a host, quality customer service matters all year round, but it’s especially important during peak season. The more positive reviews you receive on your listings, the more bookings you can expect. In turn, the easier it is to maximize your Airbnb occupancy rate.

Make sure that you always deliver consistent, friendly service. Provide fast and complete answers to any questions that your guests have before booking and during their stays. By ensuring that every guest enjoys a safe and comfortable stay, you increase the chances to receive 5-star reviews.

Finally, ask every guest to leave you a review at the conclusion of their stay. Don’t expect guests to do this on their own, especially when you’re racing against the clock to achieve as many reviews and new bookings as possible before peak season ends.

SPRING Cleaning + Update

While guests should be impressed with property's cleanliness, it doesn’t hurt to give it a makeover. This shows guests that you are dedicated to maintaining your property in the best condition possible.

You don’t even have to spend a fortune to change your property come Spring time. A few updates of the décor, such as fresh Spring flowers, Spring dinnerware for the dinner table, and lighter bed linens can attract more attention.

You should also update your photos so that they focus on amenities that people tend to use more during peak seasons, such as the swimming pool or patio. By using peak season as an opportunity to make your listings shine, you can dramatically increase your Airbnb occupancy rate.

Longer-term Rentals (1-3 months) During Off-Season

If maximizing your Airbnb occupancy rate is your primary concern during off-season, consider long-term rentals to help you fill in the gaps. 

Make sure that you adjust your listing to appeal to guests who might be looking for this sort of arrangement. Some types of guests you could target include those who are looking for study abroad accommodations or long-term business travel.

Plan Ahead to Maximize Your Airbnb Occupancy Rate

It’s not hard to keep up with your bookings when they’re fewer of them. However, managing your Airbnb or HomeAway listings can quickly become chaotic during peak season if you don’t plan ahead. In addition, peak season may vary from year-to-year, often due to circumstances that are outside of your control. You want to be prepared for these variations.

If you consider how demand for your listings changes in advance, you can ensure that you can have the resources you need ready.

5 Ways to Earn 5-Star Reviews on Airbnb


If you’re an Airbnb host, you likely face stiff competition that is only getting worse. There are almost 5,000 listings in Chicago alone, and that number is growing daily. Case in point: hosting isn’t getting any easier, and if you rest on your laurels, your business will slowly profit less and less as more supply hits the market.  

This is, unless you stay on top of your game and do everything you can to differentiate yourself from the competition.

Better reviews = more bookings = more money

Your Airbnb property is not your average rental. It is a hospitality business that requires thought and careful attention to detail. It isn’t rocket science, but most people overlook key aspects of hosting. This results in leaving money on the table. 

Here are some tips and suggestions that will help you earn five-star guest reviews and more money. We use these strategies every day while managing our properties.

1. Be Kind and Responsive

This may be the most important thing you can do to improve your revenue and attract more bookings. Many guests don’t look solely at your listing, they shop around and send out multiple inquiries at a time. These guests are looking for instant gratification. They aren’t willing to wait hours or days for a response. Aim to reply in five minutes or less. Guests will thank you for your quick reply!  

Response time is factored into your listing’s SEO.

2. Be Proactive

Being proactive helps you alleviate problems before they occur.  If you are reactive and not proactive, you’ll quickly find that you end up spending hours running around town fulfilling guest requests. Plan ahead, and you’ll prevent emergencies before they happen.  

In general, most guests are busy exploring the city and don’t want to interact with the host. They don’t need to meet you to get the key or text you for more toilet paper. Make sure to stock your home with all guest supplies, batteries, spare keys, (etc.) so that you don't have to make a mid-stay visit because you forgot something.

3. Go the Extra Mile

Sometimes you can’t plan for everything, especially on Holidays or Peak days. Guests are paying a premium for your property so it helps to provide them with extras.

One of reason to personally visit the property is when guest issues arrive. Sometimes a coffee pot breaks or wifi doesn't seem to be cooperating, but the extra effort WOWs guests and makes their stay. More importantly, it helps you avoid a bad review and clear the way for more bookings in the future!

4. Give Guests Free Goodies

Most Airbnbs I stay in offer your standard towels and sheets, maybe a coffee maker or water, but very few hosts provide extra amenities. There are so many things you can offer that cost almost nothing and add huge value to your place, bettering your guests’ experiences. Some include:

  • Granola bars

  • Bottled water

  • Coffee

  • Tea

  • Q-tips

  • Makeup removing pads

Nathan Blecharczyk, Airbnb’s cofounder and chief technology officer has found that offering a hair dryer earns hosts, on average, $10 more per night.  

My entire “guest freebies” package costs me less than $10 per stay (which I bake into the cleaning fee) and truly wows most guests.  

Note: Be aware of your city's Ordinance before providing food/water.

5. Focus on Cleaning

If your Airbnb property has one good quality, let it be cleanliness. Guests scrutinize cleanliness heavily, and having a less-than-spotless home is the quickest way to get ding'd.

Carefully train and hire your cleaning crew to pay extra attention to the kitchens and bathrooms to make sure they are 100-percent free of dirt and hair. Remember to check things like microwaves and refrigerators that can often contain hidden messes or unexpected food items. And don’t forget to dust! This is often overlooked but is a very important aspect of a clean Airbnb rental.  

There you go! These are 5 tried and true aspects of your guests' experience that will be pillars for a long-time to come. If you have a #6, please share it with us!