Top Proptech Companies in Chicago, IL (25)
Chamberlain Group is a global leader in intelligent access and Blackstone portfolio company. Powered by its myQ technology platform, CG delivers seamless, secure access solutions for millions of homeowners, businesses, and communities around the world. CG's flagship brands, LiftMaster® and Chamberlain®, are trusted in more than 36 million homes, while over 15 million users rely on the myQ® app each day...
Chamberlain Group's Top Stability & Growth Strengths
Product Line Growth: Recent launches such as the myQ Secure View 3‑in‑1 Smart Lock (Jan 2026) and updated video‑enabled LiftMaster/Chamberlain openers (Oct 2025) signal expansion beyond the garage with deeper software integration. Feedback suggests adjacent additions like cameras and a video doorbell broaden the intelligent‑access portfolio.
Market Expansion: The company is extending into new segments with myQ Enterprise for docks/logistics, myQ Community for multifamily, and in‑vehicle integrations such as the July 2026 Hyundai partnership. A new Mississippi distribution center supports a wider operational footprint.
Customer Loyalty & Retention: Company updates note myQ surpassing 10 million users in Oct 2023 and celebrating further 2026 milestones (e.g., 12 million users and references to 14–15 million daily users), indicating continued adoption. Recognition and a completed SOC 2 Type II examination in 2026 reinforce a maturing, trusted platform.
Purchasing Platform is a unique B2B marketplace tailored for all sectors of property management. We leverage cutting-edge technology to empower property portfolios, enabling them to manage purchasing activities efficiently across all properties while driving real cost savings from trusted suppliers. Our platform services portfolios across the nation, enhancing operational workflows with features like embedded multi-level workflows, automated expense classification, and...
Purchasing Platform's Top Stability & Growth Strengths
Strategic Partnerships: Partner announcements highlight a co-developed e-commerce portal with Lessen that provides access to 30,000+ vendors, and listings in PMS marketplaces like Rent Manager and Buildium extend distribution. Ongoing posts and vendor mentions (e.g., Daikin/Motili) reinforce a partner-led go-to-market motion and exposure.
Market Expansion: Materials indicate expansion from manufactured housing into multifamily and commercial real estate, with presence across PMS ecosystems that can drive steady adoption even in tighter real-estate cycles. Integration listings and third-party directories point to broader reach within property-operations workflows nationwide.
Investor Backing & Capital Strength: Documented external funding, including a $7.5M Series B in November 2022 and support from multiple institutional investors, underpins operating runway for product and go-to-market. Company scale and continued activity are consistent with a venture-backed, still-scaling private firm.
Lessen is the tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed at scale. Lessen’s technology platform provides data-driven insights that unlock key growth opportunities for the entire real estate ecosystem—including investors, owners, managers, and service providers. The company leverages a network of over 30,000 vetted, qualified vendors (Lessen Affiliates)...
Lessen LLC's Top Stability & Growth Strengths
Strong Revenue Growth: Revenue is reported to have risen from roughly $800 million in 2023 to around $1 billion in 2024, with industry recognition (Inc. 5000) highlighting exceptional multi‑year momentum. Company materials also reference ongoing increases in platform activity and customers served.
Investor Backing & Capital Strength: Capital raises include a $170 million Series B and approximately $500 million in equity and debt to finance a major acquisition, bringing total funding to the high hundreds of millions and valuation above $2 billion. This financing enabled large‑scale M&A and continued expansion.
Market Expansion: Acquisitions of SMS Assist and Blue Skyre IBE broadened reach into residential and commercial facilities management, while partnerships (e.g., Paul Davis Restoration) and a larger Chicago office signal a widening geographic and service footprint. Operations now span 100+ markets with 30,000+ vendors, serving hundreds of thousands of properties and millions of annual work orders.
Metropolis Technologies, Inc. is an artificial intelligence company whose computer vision platform enables checkout-free payment experiences for the real world. Its proprietary AI-driven technology reaches more than 50 million customers while reducing costs, increasing transparency and capturing additional revenue for real estate partners. Following its take-private acquisition of SP+, Metropolis is now the largest parking network in North America with...
Metropolis Technologies's Top Stability & Growth Strengths
Strong Market Position & Advantage: After closing the SP+ take‑private in May 2024, the company states it became the largest parking network/operator in North America with 4,000+ locations, later citing 4,200+ locations and about $5B in annual payments. This scale provides reach to 50M+ consumers and a platform for broad deployment of its AI-driven model.
Investor Backing & Capital Strength: In November 2025, the company announced $1.6B in new capitalization (a $1.1B Term Loan B plus a $500M Series D) to accelerate expansion beyond parking. Earlier financing linked to the SP+ acquisition further underscores substantial access to capital.
Market Expansion: The platform is extending into adjacent sectors—retail, hospitality, fueling, mobility, and aviation—with moves such as the Joby Aviation partnership to develop 25 vertiport sites. Acquisitions like Oosto broaden capabilities supporting expansion beyond core parking.
Airbnb is a community based on connection and belonging—a community that was born in 2008 when two hosts welcomed three guests to their San Francisco home, and has since grown to 4 million hosts who have welcomed over 800 million guest arrivals to about 100,000 cities in almost every country and region across the globe. Hosts on Airbnb are everyday...
Airbnb's Top Stability & Growth Strengths
Strong Revenue Growth: Recent results show full-year 2025 revenue rose to about $12.2B with Q4 2025 revenue up roughly 12% alongside GBV growth of about 12% for the year and about 16% in Q4. Management’s 2026 outlook calls for at least low double‑digit revenue growth with Q1 2026 guided to approximately 14–16%.
Strong Market Position & Advantage: The company is characterized as a category leader in dedicated short‑term rentals, with brand strength and scale evidenced by hundreds of millions of Nights & Experiences and expanding GBV. Commentary notes Airbnb remains the largest dedicated home‑sharing marketplace even as leadership is contested on broader OTA metrics.
Market Expansion: Late‑2025 momentum was highlighted in Brazil and Japan, with India among the fastest‑growing origin markets and expansion markets growing faster than core. Geographic breadth helped deliver the fastest quarterly GBV growth in over two years exiting 2025.
Founded in 1993, Greystar provides world-class service in the residential rental housing industry. Our innovative vertically integrated business model integrates the management, development and investment disciplines of the rental housing industry on international, regional and local levels. This unique approach and our commitment to hiring the best professionals have resulted in record growth, making us one of the most respected...
Greystar's Top Stability & Growth Strengths
Strong Market Position & Advantage: Industry rankings and company disclosures position Greystar as the largest U.S. apartment operator and a top owner, developer, and builder, with over 1,000,000 units/beds managed globally. Sustained #1 placements in the 2025 NMHC Top 50 and a broad global footprint indicate entrenched competitive advantage.
Strategic Partnerships: Recent agreements with Grand Peaks and Trilogy add nearly 11,000 units and expand presence in key U.S. markets, while the expanded CPP Investments joint venture commits $1.4 billion to single‑family build‑for‑rent. These partnerships show continued ability to scale through collaborative platforms across geographies and product types.
Product Line Growth: Expansion into single‑family build‑for‑rent, active adult housing, logistics, and an infrastructure platform broadens revenue drivers beyond traditional multifamily. Leadership cites significant near‑term expansion plans in active adult and has built a logistics footprint exceeding 12.5 million square feet in the U.S.
VTS is the commercial real estate industry’s leading technology platform that transforms how strategic decisions are made and executed across the asset lifecycle. In 2013, VTS revolutionized the commercial real estate industry’s leasing operations with what is now VTS Lease. Today, the VTS Platform is the largest first-party data source in the industry and delivers data insights and solutions for...
VTS's Top Stability & Growth Strengths
Strong Market Position & Advantage: VTS is positioned as a category leader in landlord-side leasing and asset-management workflows, with the platform described as an industry standard used broadly across major portfolios. Its scale is reinforced by claims of a very large global footprint (billions of square feet) and deep penetration in Class A office, plus adoption by marquee owners and brokerages.
Innovation-Driven Growth: Product momentum is tied to the launch of VTS AI in 2025, which is repeatedly cited as a key catalyst behind “record growth” and ongoing workflow improvements. Continued releases through 2025–2026 and AI-focused role postings indicate sustained investment in AI/data capabilities as a growth lever.
Investor Backing & Capital Strength: The company is described as having substantial funding support, including a large Series E round and strategic participation, indicating access to capital to fund product expansion and go-to-market efforts. References to valuation and funding earmarked for innovation and expansion reinforce capital strength.
AIR Communities (Apartment Income REIT Corp.), is a Real Estate Investment Trust headquartered in Denver, CO. We are one of the country's largest owners and operators of multifamily housing, managing high-quality properties in most major markets, including Boston, Denver, Philadelphia, Los Angeles, and Miami! At AIR, we value integrity, respect, collaboration, customer focus, and performance. These values are brought to...
AIR Communities's Top Stability & Growth Strengths
Investor Backing & Capital Strength: Feedback suggests Blackstone’s acquisition and commitment to invest over $400 million provides substantial financial resources and stability. The company now operates as a well-capitalized private portfolio with access to significant sponsor capital.
Strong Market Position & Advantage: AIR Communities is often described as a major player with a high-quality, large-scale apartment portfolio in high-barrier coastal markets. Statements from Blackstone characterizing the assets as the highest-quality large portfolio they have acquired reinforce perceived competitive strength.
Resilient & Sustainable Growth: Prior to privatization, same-store revenue, NOI, FFO, and resident retention showed steady organic momentum. Post-transaction commentary indicates continued focus on operational improvements and steady cash-flow generation.
Cadre is a groundbreaking technology-driven commercial real estate investment platform that offers both institutional and individual investors the opportunity to access expertly curated real estate assets with lower minimums, low fees, and unprecedented potential for liquidity. Via its data-driven and transparent approach, Cadre opens participation in a historically opaque and illiquid asset class. Since Cadre’s founding, Cadre has closed more than...
SitusAMC is the leading independent provider of innovative, trusted solutions that support the entire lifecycle of commercial and residential real estate finance, powering more efficient, effective, and agile businesses. We partner with leading lenders and investors to help them originate, transact, manage, and value their real estate portfolios. We do this through strategic outsourcing, advisory, talent, and technology solutions. ...
Gearflow is the AI-powered procurement platform built for the people who build, power, and move the world. Procurement is now at job site speed. Built alongside the industry's leading contractors, Gearflow enables fleets to grow without the support costs and chaos that comes with it. The platform is used to automate workflows, compare quotes, and centralize procurement. Built for Growing Fleets...
A real estate company with a purpose; we are building the first modern real estate platform, pairing the industry’s top talent with technology to make the search and sell experience intelligent and seamless.
Compass's Top Stability & Growth Strengths
Strong Market Position & Advantage: Feedback suggests Compass leads the U.S. brokerage industry by closed sales volume with a concentrated presence of top‑producing agents and rising national share. Additional observations highlight expanding scale via acquisitions and external recognition of executive influence.
Strong Revenue Growth: Feedback suggests quarterly and full‑year 2025 revenue reached record levels with sustained double‑digit year‑over‑year growth. Commentary also notes consistent outperformance in transactions versus the broader U.S. market.
Healthy Cash Flow: Feedback suggests the company delivered multiple consecutive quarters of positive operating cash flow alongside improving adjusted EBITDA. Management communications also emphasize strengthened cash generation and record platform engagement.
Obie is the leading investment property insurance platform, providing landlords, real estate investors, and partners with instant quotes, tailored coverage, and an entirely digital experience. Backed by proprietary technology, Obie simplifies insurance so deals can close faster and investors can move forward with confidence. Whether they’re obtaining a quote in under 5 minutes on our website, via a partner platform,...
ReloShare, Inc. is a seed-funded, B2B2C tech startup headquartered in Chicago's West Loop neighborhood with remote staff nationwide. ReloShare aims to innovate what emergency housing can look like through the elimination of barriers that have long plagued the social services field through our products: Safe Stays and The Grove. Safe Stays is a groundbreaking hotel booking application that provides safe...
Bozzuto is an experience-focused real estate company distinguished by our innovative developments, dedicated customer service and top-rated workplace culture. With award-winning expertise in homebuilding, multifamily development, construction and management, we are devoted to delivering extraordinary experiences for those we serve. Since our founding in 1988, we have developed, acquired, and built more than 62,000 homes and apartments. We currently manage...
Outcome is an AI platform tailored for the commercial real estate industry. By transforming data into actionable intelligence, reports, automations, and results, Outcome empowers businesses to operate more efficiently. Trusted by leading commercial real estate (CRE) firms, our platform helps teams save time, minimize errors, and make informed decisions faster. Outcome's mission is to enable professionals to focus on impactful,...
Outcome Labs's Top Stability & Growth Strengths
Innovation-Driven Growth: Public launch in late 2025 followed by regular 2026 product updates and a vertical AI orchestration thesis for CRE indicate active build velocity and innovation. Event participation and ongoing content reinforce a fast iteration cycle aligned to market needs.
Strategic Partnerships: A named design partner (Marc Realty), recognizable “Trusted by” logos (e.g., CBRE, Lux Living, Telis), and selection into Google’s 2026 Gemini Startup Forum point to growing ecosystem ties and collaborative go‑to‑market. These signals suggest early customer engagement and channel visibility in CRE.
Future-Ready Strategy: A formal Trust Center with enterprise security controls and listed AI/cloud subprocessors signals preparedness for enterprise buyers. This posture supports near‑term scaling and adoption within CRE organizations.
Sentral is a leading residential hospitality operator and prop-tech innovator that manages a network of urban residential communities. By offering both designer-furnished and unfurnished homes with flexible lease terms, Sentral redefines the modern living experience. Their mission is to provide convenience, connection, and comfort through tech-enabled services and premium amenities, allowing residents to live, work, and travel on their own...
Welcome to Enodo, an AI-Assisted Underwriting Platform for Multifamily. Analyze millions of properties to instantly survey rent and expense comps, identify value-add opportunities, and track your competition.
Kin helps you protect and manage your most important investments with homeowners insurance, mobile home insurance, landlord insurance, condo insurance, flood insurance, auto insurance,* and home financing through Kin Financing. At Kin, our mission is to make life simpler, more affordable, and better for homeowners — especially in places where climate risks, rising costs, and outdated systems make it hardest....
Kin Insurance's Top Stability & Growth Strengths
Strong Revenue Growth: Company disclosures show sustained year-over-year revenue increases through 2025, with sequential quarterly gains and rising gross written premium. Expansion in total insured value underscores continued top-line momentum.
Profitability: Updates indicate positive operating income since 2023 and record margins in 2025, with baseline operating income expanding materially. Managed reciprocal exchanges also reported positive adjusted net income, pointing to improving unit economics.
Market Expansion: The business entered multiple new states and quickly gained traction in challenging markets like California while adding Colorado, extending reach across a large portion of the U.S. homeowners market. Geographic growth complements traction in core catastrophe‑exposed states.
CompStak creates transparency in commercial real estate by gathering information that is hard to find, difficult to compile or otherwise unavailable. The company's data is used by institutional owners to compare properties, hedge funds to make investments, and provides meaningful data for brokers, investors, appraisers, asset managers, etc.





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