8 Ways To Boost Low-Earning Vacation Rentals in Chicago

Any vacation rental business knows that while the high season brings a steady stream of guests, the low season can be far more challenging. However, with a strategic approach, you can optimize your occupancy during off-peak times and ensure your property remains desirable year-round.

Here’s how you can boost your vacation rental’s performance during Chicago’s slower months and turn those quieter times into opportunities for growth.

Identifying Your Vacation Rental Off-Season

Chicago’s off-season typically spans the colder months, especially from January to March, when tourism slows down due to harsh weather conditions. Understanding when your low season hits is crucial for implementing strategies to maintain occupancy and revenue. Here are three ways to identify your off-season:

  1. The DIY Approach: Use local insights to gauge off-peak times:
    • Analyze Competitor Listings: Check how large property management companies in Chicago adjust their pricing. Listings in neighborhoods like River North and Lakeview often lower their prices during off-peak times.
    • Observe Hotel Pricing: Major Chicago hotels frequently update prices based on seasonal demand. Watching these adjustments can offer insights into the city’s broader tourism trends. 
    • Check Google Business Profiles: Reduced operating hours for local businesses, like museums or river tour companies, often signal a drop in tourist traffic. You can explore changes in business hours on Google Business.
  2. Use Your Historical Data: Leverage data from your Property Management System (PMS). Platforms like Hostfully allow you to pull reports that show occupancy trends across different seasons in Chicago, helping you make data-driven adjustments to your strategy.
  3. Leverage AirDNA and KeyData: For a deeper analysis of the Chicago vacation rental market, consider investing in tools like AirDNA and KeyData. These platforms provide valuable insights into local occupancy rates, average daily rates, and forecasted demand trends, offering a competitive edge.

Chicago is one of the top U.S. cities for vacation rentals, attracting millions of visitors each year. However, the market is highly regulated, and understanding local laws is crucial. Chicago’s Shared Housing Ordinance requires short-term rental operators to register with the city and adhere to specific rules. 

For instance, only a limited number of units can be rented out in a building, and there’s a cap on the number of days a property can be rented annually. For more detailed information, you can check out the City of Chicago’s regulations.

How to Optimize Occupancy During Low Season in Chicago

Once you’ve identified your off-season, use these strategies tailored to the Chicago market to attract guests:

  1. Adjust Your Minimum Stay Requirements

Lowering your minimum stay requirements can attract guests looking for short getaways. For instance, if you usually require a three-night stay, consider dropping it to two during the winter months. This flexibility can appeal to travelers visiting Chicago for quick business trips or weekend explorations.

  1. Offer Discounts with an Off-Season Pricing Strategy

Implement dynamic pricing adjustments during Chicago’s slow months to attract budget-conscious travelers. Using software like PriceLabs can help you automate rate changes based on market conditions. Consider offering extended stay discounts or last-minute deals to fill those gaps.

  1. Update Your Listing with Seasonal Photos and Keywords

Optimize your property’s appeal by showcasing it as a cozy winter retreat or an ideal spot for a spring getaway. Update your listing with seasonal photos featuring iconic Chicago backdrops, like snowy views of Millennium Park or spring blooms along Lake Michigan. Including keywords like “winter escape in Chicago” or “off-season Chicago rental deals” can improve your listing’s visibility on platforms like Airbnb.

  1. Secure Direct Booking Stays with Promotions

Direct bookings can significantly enhance your net revenue by avoiding OTA fees. Promote exclusive offers through your website, targeted email campaigns, and social media ads. Highlight unique Chicago experiences, such as discounts on local tours or tickets to a Bulls game, to entice direct bookings. 

  1. Allow Instant Bookings

Enabling instant bookings can increase your property’s attractiveness to last-minute travelers, particularly during slower months. Chicago’s frequent visitors, such as business travelers, often value the convenience of instant booking, especially when planning quick trips.

  1. Partner with Local Chicago Businesses

Collaborate with local attractions, restaurants, or tour operators to offer exclusive deals to your guests. For example, partnering with a popular Chicago deep-dish pizzeria or a local architecture tour company can provide added value to your guests and make your property stand out. Explore potential partnerships through Choose Chicago, the city’s official destination marketing organization.

  1. Invest in Your Property and Enhance the Guest Experience

Use the low season to make property improvements that cater to winter travelers. Adding amenities like a fireplace or heated floors can attract guests looking for a warm and cozy retreat in the Windy City. Small touches, such as providing a guide to nearby indoor attractions, can elevate your guest’s experience and lead to positive reviews.

  1. Implement a Targeted Marketing Strategy

Leverage digital marketing to reach new audiences. Chicago’s diverse visitor demographics, from international tourists to domestic business travelers, can be targeted through Pay-Per-Click (PPC) ads, social media campaigns, and collaborations with local influencers. Highlight what makes your property unique and why it’s perfect for an off-season stay in Chicago. 

Conclusion

Boosting your vacation rental’s occupancy during Chicago’s off-season requires a tailored approach. By identifying when your slower months occur, adjusting pricing and booking policies, enhancing your property with thoughtful upgrades, and targeting the right audience through strategic marketing, you can turn low-earning periods into profitable opportunities. Embrace the unique character of Chicago in all seasons, and position your rental as a desirable destination, no matter the time of year.

Give us a call today to find out what we can offer you! (312) 857-8572

Get More Info On Options To Sell Your Home...

Selling a property in today's market can be confusing. Connect with us or submit your info below and we'll help guide you through your options.

We Buy Houses In Chicago IL For Cash. Any Condition, Size, Age, Or Reason.

Start below by giving us a bit of information about your property or call (312) 857-8572. You'll get a fair cash offer. You choose the closing date. We pay all the costs.
  • This field is for validation purposes and should be left unchanged.