Book WIN Home Inspection in Chicago

In Chicago’s diverse housing market, knowing a home’s condition is essential. Our certified inspectors review 300+ items and pay close attention to local challenges including foundation cracks, party walls, weather impact, historic brick buildings, and high-rise condos.

  • Vintage brick bungalows
  • Townhomes
  • Two-flats and three-flats
  • Mid-century ranches
  • High-rise and mid-rise condos
  • New builds and full gut rehabs

Chicago Property Inspection Specialists

Chicago’s climate and infrastructure shape how homes age. WIN tunes each inspection to local patterns so you know what matters most.

  • Heavy rain can overwhelm drains and older sewers. We review grading, sump pumps, and backflow readiness.
  • Freeze and thaw seasons wear roofs, flashing, gutters, and masonry. We look closely at eaves and chimneys.
  • Lead present in older paint and some plumbing. We note likely sources and conditions that could disturb them.
  • Basements and baths often hold moisture. We check ventilation and insulation to support healthy airflow.
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Best Home Inspection Service in chicago, IL

When it comes to home inspections in chicago, trust WIN Home Inspection to provide you with a thorough, professional service you can rely on. At WIN, we don’t just inspect homes, we empower you with the knowledge to make the best decisions for your family and your future.

Advanced diagnostics

Infrared, moisture meters, drones, and scope cameras to see what others miss.

35+ services, one team

Full Home plus testing and assessments available when needed.

Property Care List

Complimentary, negotiation-ready list organized as Repair, Replace, or Credit.

Transparent pricing

Clear estimates before you book, with easy online scheduling.

Home Inspection Services for Every chicago Property Need

Whether you're buying, selling, or maintaining your chicago property, our expert inspectors provide specialized services designed for your specific situation and local market needs.

Top Services in Chicago
These are the most popular inspection services requested by Chicago homeowners, buyers, and sellers tailored to the city’s housing mix of historic brick homes, high-rise condos, and weather-related challenges.
  • 80%
    buyers request a home
 inspection before closing
  • 1 in 3
    inspections uncover hidden issues

A full home inspection covers your property’s structure, roof, plumbing, electrical, HVAC, foundation, and interior systems. Our inspectors deliver a digital report with photos and recommendations within 24 hours, helping you address safety issues and repair needs. Tailored for Chicago’s housing mix, it applies to everything from historic brick bungalows to modern high-rise condos.

  • 1 in 4
    homes tested show elevated mold spore levels in humid regions.
  • 48%
    of Chicago homes have basements susceptible to moisture buildup.

Chicago’s mix of older homes, basements, and humid lake weather makes moisture a year-round concern. Our mold inspection identifies hidden growth in basements, attics, and HVAC systems using advanced moisture meters and air sampling. Detecting mold early helps protect both property value and indoor air quality.

  • 1 in 3
    Chicago homes test above the EPA’s safe radon limit.
  • Recommended by the Illinois Emergency Management Agency

Radon is naturally common in Cook County and surrounding areas. Our certified inspectors use continuous radon monitors to test gas levels over 48 hours and deliver clear digital reports. Knowing your home’s radon level helps keep your family safe and ensures compliance with state and real estate disclosure rules.

  • Termites cause over $5 billion in property damage nationwide each year.
  • High-risk zones include areas with older wood siding and poor drainage.

Chicago’s older wooden structures and warm months invite termite and carpenter ant activity. Our termite and pest inspection checks wood framing, crawlspaces, and exteriors for early signs of infestation or damage. Identifying it early prevents costly repairs and helps maintain your home’s long-term integrity.

  • Heavy rain often overwhelms aging sewers in Cook County.
  • Higly recommended for homes built before 1980 or with mature trees nearby.

Many Chicago neighborhoods still rely on clay or cast-iron sewer lines that can crack or clog with tree roots. Our sewer scope inspection uses a high-definition camera to view the full line, identifying blockages or corrosion before they cause backups or flooding.

Client Feedback

What Our Chicagoland Clients Say about us

Reviews from satisfied customers across chicago and Cook County
Cris was absolutely awesome I'd 100% reccomend!
Vincent W
At WIN, we go beyond inspection. Our complimentary services help you track appliances, access concierge resources, and maintain your home with ease.
Drone Roof Inspection
WIN Home Inspection includes drone technology to accurately inspect hard to reach areas of the roof.
Property Care List
Every WIN inspection includes our exclusive Property Care List—an innovative tool to help you organize findings to repair, replace or credit.
Learn More
Drone Roof Inspection
WIN Home Inspection includes drone technology to accurately inspect hard to reach areas of the roof.

Frequently Asked Questions About chicago Home Inspections

Get answers to common questions about property inspections in chicago and Cook County

WIN is the Most Innovative Home Inspection Services Company.

To deliver actionable insights for hard to access spaces such as attics, roofs, chimneys, sewer drain lines, interior walls, vents and crawlspaces, we utilize state-of-the-art tools and technologies including drones, infrared scanners, 3D and 2D imaging, scope cameras, and robotics. Every inspection comes with a clear, visual digital report so you can make confident decisions.

Find Your Local Home Inspectors in chicago

With inspectors based in and around chicago, WIN combines national resources with local expertise. Our team uses advanced tools—like infrared (IR) scanners, sewer scope cameras, and moisture meters—to detect and help protect your investment.  

Schedule your WIN Home Inspection?

Join thousands of satisfied chicago homeowners who trust WIN Home Inspection. Get your detailed report in just 24 hours.

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Steve is a great guy, very professional and patient. He really takes the time to go over every question you have with the inspection!
- Eddie Wong