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Chicago’s Growing Airbnb Culture
May 29, 2024

Chicago’s Growing Airbnb Culture

33 realty
Chicago’s Growing Airbnb Culture
Chicago's Growing Airbnb Culture

From extremely modern to high-end boutique, Chicago’s neighborhoods are full of unique hotels, but there’s a growing trend for accommodations in the city that has nothing to do with hotels. Airbnb changes the way you stay in Chicago, and the options are anything but boring.


Airbnb gives property owners with space to rent a place to connect with travelers looking for a place to stay. The owner posts the property with images and details of the rental. Potential renters browse the listings, and when a user finds a place to rent, booking and payment take place online. It’s an easy way to rent out your extra space or a vacation home you only use occasionally.

Airbnb benefits for property owners include:

  • Meeting people from all over
  • Supplementing income
  • Easy management of rentals
  • Increased profits over long-term rentals

Renters get a unique experience instead of being limited to hotels. Many Airbnb users want to save money over staying in a hotel in the same area. Others look for truly unique accommodations in a home-like atmosphere. Chicago has some amazing Airbnb locations that wow visitors to the city.

The benefits of using Airbnb for the renters include:

  • Personalized attention from hosts
  • Excellent customer service from Airbnb
  • Option to check reviews before booking
  • Often cheaper than hotels
  • Locations in neighborhoods to fully experience the culture
  • Unique buildings
  • Private accommodations‍


Some Airbnb options fulfill your basic needs. You get a place to sleep, a kitchen, a bathroom — just the basics. Others go way beyond average with creative decorating themes, unique buildings and designer touches. While some people go for affordability, many want the experience of staying somewhere unique. The city has many of those standout options that solve the dilemma of where to stay in Chicago.

What are some popular Airbnb rentals in Chicago? Check out these unique offerings in the city:

  • Wicker Park Converted Church

    See church in a new light with a stay at this one-bedroom rental in a converted church. The building still features stained glass windows, beautiful woodwork and amazing 35-foot ceilings. Its location directly across from Wicker Park adds to the appeal, and renters get free parking, which is always a bonus in Chicago.
  • Wicker Park Artist Loft

    Nestled in Wicker Park, this private room rental in an artist loft gives you access to a sauna, fireplace and rooftop deck. Enjoy the rainforest shower head and two-person soaking tub in the bathroom. You even get a personal parking spot in a gated area.
  • Historic Florsheim Mansion

    Stay in the former home of a shoe heiress and sculptor with this Chicago Airbnb. The Florsheim Mansion for the Arts features five bedrooms and five bathrooms between the main house and guest house, making it perfect for large groups.

    Unbelievable architecture and detailing leave you in awe over this Gold Coast home. The mansion serves as home to an artist-in-residence program, with part of the Airbnb rental proceeds funding the program. Your stay supports artists, making this option even more unique.
  • Luxury Loft

    This luxury loft situated near Bucktown and Logan Square lets you enjoy plenty of space — 26-foot ceilings and beautiful skylights to fill the space with sunlight. The seven-bedroom loft holds over 20 guests, so it’s ideal for large parties. Just a few of the amazing features include a gourmet kitchen, garden patio, rooftop deck, full-size bar and timber beams on the ceiling.
  • Lincoln Park Penthouse

    Book a stay at this Lincoln Park penthouse for easy access to parks, beaches and walking trails. The vintage building adds to the charm of this rental. Three bedrooms and two bathrooms provide ample space in this apartment. Step out on the spacious deck for a lush green view in the middle of the city.


Airbnb’s impact in Chicago is a hot topic of conversation among property owners, city government leaders and community members. Some argue that the sharing economy of Airbnb rentals hurts an already pricy housing market. Short-term rentals take away the option for longer term renters to claim that space, leaving fewer rental options on the market and driving up the prices. Opponents feel it takes away from the sense of community because renters stay only short periods.

Proponents of Airbnb have differing opinions. They suggest Airbnb rentals bring money into the Chicago communities where they are located. A visitor who might normally choose a hotel in the heart of Downtown Chicago might instead choose a unique rental in a different neighborhood. The restaurants, boutiques and other businesses in that area earn revenue from those renters.

The home-sharing market offers a major benefit for Chicago property owners. Short-term vacation rentals often net more money than longer-term rentals. Airbnb investment real estate gives the owner a major source of income to offset the cost of the mortgage. For homeowners who rent a room or the whole unit, home sharing is a way to supplement income or help pay for the home. For business owners with investment properties, it maximizes profits.

airbnb investment is a major source of income


The increase in popularity of Airbnb rentals has caused many cities to take a closer look at the situation. In an attempt to control the negative impact on the community, some cities make the practice of whole home sharing illegal. In other words, renting out an entire single-family home is not allowed in some cities, but renting out a single room within the home is acceptable.

Chicago passed regulations in 2016 to control home sharing. Airbnb property owners generally feel the regulations are unfair to them while some home sharing opponents feel there is room for more regulation. Here are some components of the regulations:

  • Extra tax on the income generated from the property
  • Cap on how many units in a building can be rented via Airbnb — 6 units or 25 percent of the total units, whichever is smaller
  • Requirement for hosts to keep records on guests
  • Inspections of rentals from building commissioners
  • Primary residence requirement for single-family homes and buildings with two to four units

Another component is the Prohibited Housing List. Essentially, the owner of the building can place units on the list, meaning those spaces are ineligible for renting on Airbnb and similar sites. As of January 2017, about 91,000 apartment and condo units were on the list. That may sound like a lot of units, but it’s only about 7.6 percent of all Chicago housing units, so there are plenty of properties not on the list.

prohibited housing

The list of properties on the list is concentrated highly in the downtown area, although there are properties throughout the city that don’t allow home sharing. Always check before purchasing a property as a rental. It’s important to stay current on regulations governing home sharing in Chicago. No matter how tempting it is to rent out a unit for profit, ignoring the rules can result in hefty fines.


Evaluate your readiness to jump into an Airbnb rental business with these questions:

  • Do you have the means to fund the investment or secure a loan for the property?
  • Can you cover the payments even if you don’t constantly rent out the property
  • Are you comfortable with strangers in your home?
  • Do you have adequate insurance coverage to protect your home and your financial future?
  • Do you enjoy providing customer service?
  • Are you prepared for the possibility of damage to the property?
  • Have you read the latest regulations for Chicago Airbnb properties, and are you willing to abide by them?
  • Do you have time to manage the bookings?
  • Is the extra income worth the work?
  • Will you handle cleaning, check-in and check-out, customer service and other issues yourself? If not, can you still make a profit when you hire someone to handle the work?


The top Airbnb rentals in Chicago have something unique about them. They stand out for one or more reasons as an experience to remember rather than just a place to stay while in Chicago. When considering investment opportunities that Airbnb can provide in the city, look for one or more of these factors:

top airbnb rental experience
  • Location

    Chicago visitors want a convenient or unique location. Look for investment properties in hot neighborhoods close to restaurants, entertainment and attractions. Look at the location from a renter’s perspective. Renters want neighborhoods that are safe, close to amenities and interesting.

    Consider the distance to public transportation. If the property is just a short walk to the L, renters can still access any attractions in the city. Investing in a property with a prime Chicago location increases your chances of filling up your calendar with rentals.
  • Amenities

    What extras does the property offer? Does it have outdoor space, a hot tub, great views or a gourmet kitchen? Those extra touches make your rental more appealing to vacationers who want a unique experience.
  • Compliance

    Regulations can change at any time, so make sure a potential investment property meets current Airbnb regulations set by the city. Ensure the property isn’t on the Prohibited Housing List. Verify that the building association or homeowners’ association doesn’t have restrictions in place on home sharing.
  • Size

    The size of the unit is another factor to consider. Larger spaces naturally rent for higher prices. Some people want to accommodate a whole family. Others use Airbnb to find even larger spaces for reunions, retreats or other large-group travel. You have the option to rent out individual rooms or live in part of the home while renting out the rest to increase your potential for profit.
  • Style

    Chicago homes with a distinct style often gain attention on Airbnb. The converted church is the perfect example. The unique building style draws more people. You don’t need to buy an old church to have a popular rental option. You might choose a modern-style loft space or a vintage apartment with exposed brick walls.
  • Layout

    Choose a home with a layout conducive to renting out the space. If you plan to live in the home and rent out rooms, does the layout afford both you and the renters some privacy? Can the renter easily access areas they have permission to use? Is there enough space to comfortably accommodate renters?
  • Parking

    Having a place to park a car is a big selling point for visitors to Chicago. Parking can be a nightmare, and it is often expensive. Look for a property with on-site parking that you can offer to your renters.


If you’re already a property owner in Chicago, upgrading your home could be the ticket to seeing increased bookings through Airbnb. Consider areas of the space that aren’t functional or don’t meet their potential. Simple cosmetic updates or renovations can make your Airbnb more appealing.

simple updates for your airbnb

Here are a few ideas to boost your bookings:

  • Outdoor Spaces

    Work on improving any outdoor spaces your property has from a simple balcony to an actual backyard. Clean up the space, and add seating if the space allows. Other options to upgrade outdoor spaces include more plants, BBQs, hot tubs, patios and decks.
  • Unique Amenities

    Simple additions to your home can make it more appealing. Install a rain showerhead or offer free Wi-Fi and free parking. Add a fireplace to your living room. The little perks add up to make your space a popular short-term rental.
  • Updated Finishes

    Does your space feel outdated? Peeling paint, worn-out furniture and outdated furnishings show up in the Airbnb photos. Take time to fix up any areas that need a little TLC.
  • Distinct Theme

    If your Airbnb property lacks personality, add some decorative touches to give it a distinct theme. Play off the overall design of the space when choosing your theme. If your space is a modern loft, play up the contemporary industrial vibe in your color choices, furniture and decorations.
  • Homey Touches

    One of the biggest draws of an Airbnb rental is the unique home setting. Capitalize on that by adding little accents that make it feel more like home. Hang artwork on the wall, places flowers in a vase and display coffee table books in the living room. Simple touches can make a big impact.

    One way to identify upgrades you need to make is to spend the night in your own rental from the perspective of a renter. If you were to rent that space for a vacation, what would you like? What would you dislike? What would you change? Base your updates on the answers to those questions, as many of your renters will feel the same way.

Ready to invest in a Chicago property? Contact 33Realty for assistance, or browse our other blog topics to learn more about improving your real estate investments.

Written by:
Drew Millard

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