Is Investing in Airbnb Rental Property in Chicago Worth It?

Airbnb has been a popular way to rent out properties to both tourists and locals. However, investing in vacation houses in Chicago in 2023 might not be the best idea.

Here are seven reasons why: 

  1. High competition: Chicago is a highly competitive market with a large number of Airbnb listings. There are over 9,000 active Airbnb listings in Chicago, and this number is expected to grow in coming years. It may be difficult to stand out among so many other listings. 
  2. Local regulations: The city of Chicago has strict regulations for short-term rental properties, including Airbnb rentals. The city has implemented strict licensing requirements and increased fees for Airbnb hosts. This creates an additional barrier to entry and may make investing in Airbnb rental properties less profitable. 
  3. Limited Rental Periods: Chicago’s rental market is largely seasonal. The city benefits from tourism in the summer months, but the demand drops significantly in the off-season. This means that investing in an Airbnb in Chicago might not be a profitable endeavor for the entire year. 
  4. Risk of Unstable Bookings: With over 9,000+ active vacation rentals and short-term listings in Chicago, there is a significant risk of unstable booking patterns. This means that an investment property may have several empty nights that can significantly reduce its profitability. 
  5. Regulatory Changes: Airbnb regulations in Chicago and other cities are constantly changing. This makes it difficult for investors to plan and invest in long-term rental properties. They may face sudden regulatory hurdles that can significantly impact their property’s profitability. 
  6. Competition from large hotels: Chicago is home to many large-scale hotels that offer competitive rates and services to tourists. As a result, Airbnb rental properties may have difficulty competing with the amenities offered by larger hotels in the city. 
  7. Maintenance costs: Since Airbnb properties are not managed by an on-site staff, maintenance and repair costs need to be covered by the owner. This can significantly reduce the profitability of the property and can be difficult for long-distance landlords. 

Vacation Rental Property Market in Chicago 

If you’re considering investing in a rental property in Chicago, it’s important to understand the local Airbnb market and its potential for profitability. When it comes to the Airbnb rental property market in Chicago, there are a number of factors to consider before making a decision.

  • Market Saturation: With so many rental properties available on Airbnb, competition for bookings can be tough.
  • Legal Restrictions: The city of Chicago has strict regulations on short-term rentals, which can limit your ability to host guests.
  • Seasonality: The demand for rental properties in Chicago can vary greatly depending on the season, which can impact your potential income.
  • Changing Market: The vacation rental homes and apartments market is constantly evolving and can be unpredictable, making it hard to plan for the long-term.
  • Neighborhood Differences: Each neighborhood in Chicago has its own unique set of rental opportunities and challenges. It’s important to conduct thorough research on each area you might be interested in.
  • Managing Your Property: Managing an Airbnb rental property takes time, effort, and money. It can be difficult to juggle multiple properties if they are not managed properly.
  • Unforeseen Issues: Maintenance and repair issues can arise unexpectedly, which can impact your profitability.
  • Changes in Taxation: Tax laws surrounding short-term rental properties are constantly changing, and can affect your income.
  • Security Concerns: When you rent out a property on Airbnb, you are inviting strangers into your home. This can be a security risk if not properly managed.
  • Covid-19 Impact: The effects of the global pandemic on the travel industry cannot be underestimated. Travel restrictions and reluctance have led to a significant decrease in demand, which will definitely have an impact on profitability.

? Key Takeaway:  Investing in Airbnb rental properties in Chicago can be lucrative, but it’s important to thoroughly research and consider all the potential challenges and risks.

Finding the Right Airbnb Rental Property in Chicago 

When it comes to investing in rental properties, one of the biggest factors that determines success is finding the right property. For Airbnb rentals in particular, there are a few key things to consider when looking for the right property in Chicago.

  1. Location is key: Look for properties that are located in popular or trendy neighborhoods that are frequented by tourists. Areas like River North, Streeterville, and Lincoln Park are popular choices for visitors.
  2. Check the regulations: Chicago has specific regulations for short-term rentals, so make sure to research them thoroughly before purchasing a property. Some areas may have restrictions or require permits, so it’s important to know what you’re getting into.
  3. Analyze the potential for income: Look at the average nightly rates and occupancy rates in the area you’re interested in. This will give you an idea of how much rental income you can expect to generate.
  4. Consider the property’s amenities: Certain amenities, like a hot tub or a rooftop deck, can make a property more attractive to renters and allow you to charge a premium rate.
  5. Look for a property with low maintenance costs: When you’re choosing an Airbnb rental property, it’s important to keep maintenance costs in mind. Look for properties that are in good condition and don’t require a lot of upkeep.

As you search for the perfect Airbnb rental property in Chicago, keep in mind that finding the right one can take time and effort. But with careful research and analysis, you can identify a property that will generate sustainable income and provide a great experience for your renters.

? Key Takeaway:  When investing in an Airbnb rental property in Chicago, consider location, regulations, potential income, property amenities, and maintenance costs as crucial factors in finding the right property. 

Chicago Short-Term Rentals Investment Opportunities 

Chicago has been a hot spot for Airbnb stays since the beginning of the home-sharing giant’s rise to prominence. With its world-class dining, vibrant nightlife, and beautiful architecture, it’s easy to see why so many people are drawn to this city. However, investing in vacation rentals in Chicago in 2023 might not be worth it. Here are 10 reasons why:

  1. Increased competition in the market could lead to lower occupancy rates and fewer bookings for your property.
  2. The city of Chicago has imposed strict regulations on short-term rentals, which could limit your ability to rent out your property.
  3. The cost of owning a property in Chicago is high, which could make it difficult to earn a significant return on your investment.
  4. Property taxes in Chicago are among the highest in the country, which could eat into your profits.
  5. The cost of living in Chicago is also high, which could make it difficult to attract renters willing to pay high prices.
  6. The city experiences harsh winters, which could make it difficult to attract renters during the off-season.
  7. Other vacation destinations may offer more attractive investment opportunities with better potential for returns.
  8. Airbnb’s business model is prone to risk, with regulations and economic downturns posing threats to profits.
  9. The COVID-19 pandemic has influenced the way people travel and increased the potential for unexpected losses.
  10. The burden of managing an Airbnb property can be significant, requiring time and resources that may not be worth the investment.

? Key Takeaway:  While Chicago remains a popular vacation destination, investing in Airbnb properties in the city may not offer the returns and ease of management that many investors seek.


In conclusion, while investing in Airbnb Chicago seems like a viable option, the projected trends indicate that it might not be worth it in 2023. From regulatory concerns to rising competition, the risks outweigh the rewards. However, this doesn’t mean that you should give up on real estate investments altogether. There are still lucrative options out there that will help you grow your wealth in the long run.

If you’re looking to invest in real estate, it’s important to conduct thorough research and analyze the market constantly. Keep an eye on emerging trends and take calculated risks. Consult with experts in the field who can guide you through the process and help you make informed decisions.

So, if you’re ready to take the plunge, don’t hesitate to explore other options.

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