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Rental Arbitrage in Chicago, Everything You Need to Know

Rental Arbitrage in Chicago, Everything You Need to Know

Chicago, the vibrant metropolis on the shores of Lake Michigan, offers numerous opportunities for real estate ventures. Among these opportunities, rental arbitrage has emerged as a popular and lucrative way for savvy investors and aspiring entrepreneurs to capitalize on the city's ever-growing demand for short-term accommodations. In this article, we'll explore the concept of rental arbitrage, its potential benefits, and important considerations to keep in mind when embarking on this exciting venture in the Windy City.

Understanding Rental Arbitrage:

Rental arbitrage is a unique real estate strategy that involves leasing a property from a long-term landlord and then re-leasing it on a short-term basis, typically through platforms like Airbnb or Vrbo. The goal is to generate profit by charging higher nightly rates to temporary guests than the monthly rent paid to the property owner. In essence, rental arbitrage thrives on the difference between long-term and short-term rental rates.

Rental Arbitrage in Chicago: Initial Costs to Consider

Rental arbitrage in Chicago presents an attractive investment opportunity with its low initial costs compared to traditional real estate ventures. However, it's essential to be aware of the expenses involved to set up your short-term rental business successfully. Let's take a closer look at the initial costs you can expect when venturing into rental arbitrage in the Windy City.

Initial investment range:

To kickstart your rental arbitrage venture, you should budget anywhere between $3,000 to $5,000. This amount includes various essential expenses such as deposits, furnishing, amenities, legal paperwork, and LLC incorporation.

Deposit and rent:

Securing a long-term lease with the property owner will require you to pay a rental deposit, along with the first and last month's rent. This initial payment ensures your agreement with the landlord and allows you to begin setting up your short-term rental operation

Furnishing costs:

Opting for a semi-furnished property is a smart move, as it can significantly reduce your furnishing expenses. However, if the property is not furnished or requires additional items, you may need to allocate around $3,000 to $5,000 for furnishing the space. Look for affordable furniture and decor options at stores like Home Depot, IKEA, and even Walmart.

DIY photography:

Cut down on professional photography costs by taking high-quality photos yourself using your smartphone. Modern smartphones often have impressive camera capabilities, allowing you to showcase your rental property beautifully without the need for expensive photography services.

Cleaning services:

While initial cleaning costs are included in the starting expenses, you may eventually need to invest in regular cleaning services. If you have the necessary skills and experience, consider handling the cleaning yourself to save money. However, if time is a constraint or you prefer professional cleaning, budget approximately $50 to $250 depending on the size and location of your property.

Legal Consultation:

Maintaining a professional relationship with a real estate lawyer is a wise decision, as Airbnb regulations can change periodically. Legal guidance can help you adapt your business practices accordingly, ensuring compliance with the latest rules and regulations. In case of any disputes with the landlord or guests, a real estate lawyer can prove invaluable, assisting with damage claims and insurance matters.

Navigating Legality and Regulations for Short-Term Rentals in Chicago

As the short-term rental market continues to grow in Chicago, hosts must be well-versed in the city's laws and regulations to ensure compliance and a successful rental business. Let's delve into the key legal requirements and regulations you need to be aware of when operating a short-term rental in the Windy City.

Vacation rental license:

You must obtain a "vacation rental" license from the City of Chicago to operate a vacation rental. Section 46300 of the Municipal Code outlines the licensing procedures and responsibilities for vacation rental permit holders. Before advertising on platforms like Airbnb, your property must be registered and approved by the BACP (Business Affairs and Consumer Protection) department.

Bed and breakfast permit:

For properties operating as a bed and breakfast, a "Bed and Breakfast" permit is required. Section 46290 of the Municipal Code details the licensing procedures and obligations for B&B licensees. Similar to vacation rentals, B&Bs must be registered and approved by the BACP before being listed on intermediary platforms like Airbnb.

Hotel license:

If you intend to run a property as a hotel, a "hotel" license is mandatory. Section 46180 of the Municipal Code provides information on licensing procedures and the duties of hotel license holders. Like other short-term rentals, hotels must be registered and obtain BACP approval before being listed on platforms like Airbnb.

Zoning regulations:

Complying with Chicago's Zoning Regulations is essential. Ensure your property meets the city's zoning requirements and land use definitions. Refer to the Shared Housing Amendments to the Municipal Code for specific details on short-term rentals.


Short-term rentals in Chicago are subject to various taxes. This includes a 4.5% hotel room tax, a 4% shared housing surcharge, and a 2% domestic violence surcharge for bookings of 29 nights or less. Airbnb collects and remits these taxes on your behalf. Additionally, Cook County imposes a 1% hotel accommodation tax, which Airbnb also collects and remits.

Other rules and contracts:

Apart from legal requirements, it's vital to abide by other applicable rules, such as lease agreements, apartment or cooperative committee regulations, homeowners' association rules, or tenant organization rules. Review your lease and consult your landlord when necessary.

Reasons for laws and regulations:

These laws and regulations are established to maintain control over the short-term rental market and promote affordable housing options for local residents. As commercial investors enter the vacation rental business, these measures aim to strike a balance between economic growth and community welfare.

Top Areas for Rental Arbitrage in Chicago

If you're considering starting a rental arbitrage business in Chicago, identifying the best neighborhoods to invest in is a crucial step. Based on data from Airbtics, two standout areas with excellent potential for rental arbitrage are West Town and the Heart of Chicago.

West Town:

West Town emerges as a prime market for rental arbitrage in Chicago. With a staggering 9,948 Airbnb listings, including 3,112 one-bedroom units, the area offers a wealth of opportunities for short-term rentals. On average, hosts in West Town generate monthly revenues exceeding $2,000, and the occupancy rate surpasses an impressive 44%. These numbers indicate a thriving short-term rental market in this vibrant neighborhood.

Heart of Chicago:

For those seeking another highly lucrative area for rental arbitrage, the Heart of Chicago stands out as an excellent choice. The neighborhood presents a significant market for short-term accommodations with over 4,000 Airbnb listings, including 1,400 one-bedroom units. Hosts in the Heart of Chicago enjoy monthly revenues exceeding $2,258, with an impressive occupancy rate of over 56%.

In Conclusion

Chicago presents a dynamic and thriving landscape for rental arbitrage, offering lucrative opportunities for entrepreneurs seeking to capitalize on the city's vibrant short-term rental market. By understanding the local regulations, carefully selecting the right property in prime neighborhoods, and providing exceptional guest experiences, hosts can pave the way for a successful rental arbitrage business. With low initial costs and the potential for significant cash flow, embarking on this venture can lead to both financial gains and a rewarding journey in the ever-evolving world of short-term rentals in the Windy City. Happy hosting!

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