Live in Chicago? This Side Gig Could Earn You Money All Year Long

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So you live in Chicago — home of Millennium Park, Navy Pier, a Tyrannosaurus rex skeleton named Sue and the tallest skyscraper in the country.

Have you thought about becoming an Airbnb host? Thousands of Airbnb hosts list places in and around Chicago, according to data from the home sharing platform.

Chicago is a great place to host because it has countless tourist attractions — although the tourism is really seasonal. 

“No one comes to Chicago in January. In the spring, it starts going up. By summer, we’re booked 90% of the time,” says Jorge Goldwater, an Airbnb Superhost. 

In a city that’s so expensive to live in, listing your home can be a great way to supplement your income. Between sporting events, conventions, attractions like the Field Museum of Natural History, and annual events like the Lollapalooza and the Chicago Blues Festival, there’s often a high demand for space.

If you’re curious to see how much money you could make by listing your Chicago space, use the Airbnb calculator:

Then, follow our step-by-step guide to set up a listing in the Chicago area.

How to Create the Best Airbnb Listing in Chicago

Before becoming an Airbnb host, you’ll want to check your local laws and prepare your space for guests. (We’ll get into that later.) Creating a listing itself is simple, but you’ll want to put some thought into it, so your space stands out from all the others.

We’ll walk you through the process, plus share some pro tips from Goldwater, a software manager who lists two bedrooms in his three-bedroom rental house near DePaul University. He’s been hosting for four years.

Answer Some Quick Questions About Your Space/Amenities

In this first part of setting up your listing, you’ll answer some basic questions about your space, which could be anything — an apartment, an extra bedroom or house, a campsite, yurt or even an RV, depending on your local laws.

Basic questions in this section include the number of guests your space can accommodate and the included amenities.

If you don’t have an entire place, list your spare room.

Set the Scene With Photos

With Airbnb listings, photos are everything. 

“Make your pictures bright,” says Goldwater. “Don’t skimp on the pictures. Try hard to make it look pretty. Then, when guests come, make sure the reality matches what the pictures look like.”

The platform offers some basic photo tips, which include utilizing natural light, avoiding flash, and shooting in landscape mode from the corners of rooms, so you add perspective.

“Declutter the house,” Goldwater advises. “No one likes clutter.”

Think about what makes your space and your location appealing, and illustrate those elements through photos. You might also include photos of the surrounding neighborhood and nearby tourist attractions. Specific locations and neighborhoods mean a lot in Chicago, so be sure to highlight that.

Write a Description

Once you hook people with your photos, continue to lead them through your listing with the description.

Here, you’ll be able to highlight what makes your space unique. If you’re not sure where to start, take a look at other Airbnb listings in your area to see what other hosts highlight. 

After you host several guests, you’ll get to know your audience, so you can lean into that. 

Name Your Listing

This might seem like a small task, but naming your listing is just as important as nailing your photos. Airbnb urges hosts to create a title that highlights what’s unique about the space.

Chicago hosts often include their specific neighborhood in their listing. You’ll see lots of listings with names like “Sunny Bedroom in Logan Square Area” or “Hyde Park Studio” or “South Loop Suite.”

Set Expectations

Make sure the reality matches what your listing promises. Your guests won’t want surprises.

“We’re right next to a train station,” Goldwater says. “Most people get used to it very fast, but every once in a while we get someone who can’t sleep.

“So I set the expectations in a very straightforward way. I tell people upfront that we are very close to a train station. There is one brick wall between us and the station.”

Set House Rules

Airbnb has a set list of rules you can opt into if you’d like them included in your listing. A few of these include: suitable for pets, smoking not allowed and events or parties not allowed. You also have the option to write in additional rules.

“I only have one house rule,” says Goldwater. “Be polite.” 

Set up Your Calendar

Taking time to set up your calendar is important, because if you cancel on your guests, Airbnb will charge you a penalty fee.

A few questions you’ll answer include:

  • How often do you want to have guests?
  • How much notice do you need before a guest arrives?
  • When can guests check in?
  • How far in advance can guests book?
  • How long can guests stay?

You’ll be able to adjust these settings as you go, so you can find out what works best for you.

Price Your Space

Airbnb has a Smart Pricing tool, which you can opt into to automatically adjust the price of your listing according to demand. For example, when the demand spikes during the Chicago Blues Festival every June, Airbnb will likely increase the price of your listing automatically.

You can set price minimums and maximums, so your listing won’t dip below a certain amount or spike to something unrealistic. Although Airbnb will suggest these amounts when you’re signing up, Goldwater urges new hosts to do their own research.

“For me, the pricing tool has been very helpful,” Goldwater says. “Especially when I first started doing this.”

Here are a few tips to help you determine these numbers:

  • Consider your expenses, i.e. utilities, cleaning and any maintenance requirements.
  • Be realistic.
  • Search other Airbnb listings in your area and price just below those.

When you’re starting out, you’ll want to price your place lower, so you can get guests in and accumulate reviews, which will help increase bookings in the long run.

Note Your Local Laws

Airbnb advises you to follow your local laws about short-term rentals, whatever they may say.

In Chicago, you are required to register your home with the city. But Airbnb lets you complete this process on its platform.

“In Chicago, it’s easy,” Goldwater says. “You make your listing in Airbnb, and they take care of all the work. The city processes it.”

Airbnb also collects and remits all relevant taxes in the city of Chicago on your behalf.

Also Consider…

In addition to hosting laws, you’ll also want to check with your condo association, landlord or homeowners association to make sure short-term rentals are permitted.

Also note that short-term rentals could invalidate some homeowner’s insurance, so check these policies with your provider.

As you start booking guests, you’ll also want to keep tabs on expenses and revenue for tax purposes.

Goldwater also reminds hosts to take advantage of tax deductions. Because he has guests staying in his space, he can deduct many charges as business expenses, including utilities, furniture, home improvement, even electronics — basically anything guests will also benefit from or use.

Ready to Give This Whole Hosting Thing a Try?

How are you feeling? Like we said, listing your place on Airbnb is simple — but it does require some creativity and strategy. The good news is you can adjust or change your information and settings at any time, so you’re not locked into anything permanently.

Goldwater’s favorite part of hosting has been all the interesting people he’s met. Many of his guests are parents and their college-age children who are on college tours and who stay with him while they visit DePaul and other nearby colleges. He also gets Cubs fans and visitors who are in town for various summer festivals.

“People are nice and polite,” he says. “I’ve been doing this for a long time, and I’ve never had any negative experiences. It’s been overwhelmingly positive.”

“Try it out, because you have nothing to lose,” he says. “If you decide you don’t like it, just stop listing your place.”

Mike Brassfield ([email protected]) is a senior writer at The Penny Hoarder.





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