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Chicago Landlord Winter Guide: Avoid Costly Damages

Learn how to protect your rental property, prevent costly repairs, and navigate Chicago’s changing real estate market. In this episode of The Housing Provider Show, Tim Harstead and Dave Bovyn break down 2025 landlord strategies, winterizing your property, market trends, evictions, tenant disputes, ICE-related leasing delays, and how to avoid losing money this season. 

What you’ll learn: Chicago housing market update & interest rate changes 

  • Why 2025 is a “weird” buyer’s market 
  • How landlords should winterize rentals to prevent frozen pipes 
  • Why preventative furnace maintenance saves thousands 
  • Tenant communication rules for freezing temps 
  • How ICE activity is affecting leasing, employment & rent payments 
  • How to handle evictions, non-renewals & legal notice timelines 
  • Dealing with noise complaints and petty tenant disputes 
  • How lease wording protects landlords from liability 


๐Ÿ‘‰ SUBSCRIBE for Chicago real estate insights, landlord tips, and property management advice. 

๐Ÿ‘‰ LISTEN to the full episodes on Apple Podcasts , Youtube & Spotify 

๐Ÿ‘‰ Work with our property management team https://www.chicagostylemanagement.com/

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