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Top Proptech Companies in Chicago, IL (29)

Chamberlain Group
Automotive • Hardware • Internet of Things • Mobile • Software • App development • PropTech
We make access simple and secure.

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...

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Chamberlain Group

Chamberlain Group's Top Stability & Growth Strengths

Market Expansion: Expansion beyond garage-door hardware into software, smart-home, commercial-access, and connected-vehicle services is broadening the company’s addressable market. Acquisitions and a focus on multifamily properties, warehouses, and loading docks further extend reach across adjacent segments.

Product Line Growth: New offerings such as video-enabled openers, outdoor security cameras, and the myQ Secure View 3-in-1 Smart Lock extend the portfolio from garage access to whole-home security. This broadening of products supports cross-sell opportunities across residential and commercial use cases.

Strategic Partnerships: Integrations with major automakers including Hyundai, Honda, and Acura embed myQ directly into vehicles. These alliances deepen ecosystem adoption and open additional OEM distribution channels.

Metropolis Technologies
Artificial Intelligence • Computer Vision • Machine Learning • Payments • Real Estate • PropTech
7 Offices
23,100 Employees
60 Benefits Hiring Now
Metropolis is an artificial intelligence company for the real world.

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...

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Metropolis Technologies

Metropolis Technologies's Top Stability & Growth Strengths

Investor Backing & Capital Strength: Access to capital is described as strong, highlighted by approximately $1.6 billion in 2025 financing (a ~$500 million Series D plus a $1.1 billion term loan) at an estimated $5 billion valuation. This funding is positioned to support expansion beyond parking into areas such as airports, retail, fueling, hospitality, and drive‑throughs.

Strong Market Position & Advantage: Operating scale is portrayed as substantial after the SP Plus acquisition, creating 4,000+ locations and 20,000+ employees and later exceeding 4,200–4,500 locations. Combining this footprint with AI-driven, checkout‑free capabilities positions the company as a leading North American parking operator.

Market Expansion: Reach is widening with reported deployments at 100+ airports and moves into adjacent categories like fueling, drive‑throughs, hospitality, and retail. Reported growth to 21–30+ million members and continued location additions indicate an expanding addressable market.

Lessen LLC
Cloud • Real Estate • Software • PropTech
Help us revolutionize real estate services.

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)...

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Lessen LLC

Lessen LLC's Top Stability & Growth Strengths

Strong Revenue Growth: Revenue is described as approximately $800 million in 2023 with expectations to exceed $1 billion in 2024, and a top-two placement on the 2024 Inc. 5000 underscores exceptional multi-year expansion. While privately reported, these indicators collectively point to significant historical scaling.

Market Expansion: The platform reports reach across about 1.8 million properties, service in 150 metropolitan areas, and a network of 34,000 vendors, with scope augmented by the SMS Assist acquisition and expansion into Canada. These figures indicate substantial national operating scale across residential, multifamily, and commercial portfolios.

Innovation-Driven Growth: New offerings such as the AI-powered Aiden platform and tools like Lessen Copilot, alongside integrations with systems like RealPage and HappyCo, reflect ongoing investment in technology. These launches suggest the product portfolio is widening to support growth in property-operations workflows.

Purchasing Platform
eCommerce • Real Estate • PropTech
Chicago
30 Employees
71 Benefits Hiring Now
Purchasing Platform is the online marketplace for the property management industry.

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...

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Purchasing Platform

Purchasing Platform's Top Stability & Growth Strengths

Market Expansion: Positioning has broadened beyond manufactured housing into multifamily, commercial real estate, contractors, and other property-related markets. These moves expand the addressable customer base and support further adoption across multiple segments.

Strategic Partnerships: A partnership with Lessen extends access to the company’s e-commerce portal to a large vendor network, and listings within property-management ecosystems (e.g., Buildium and Rent Manager) create additional routes to customers. These distribution levers are presented as catalysts for scalable reach without equivalent direct sales expansion.

Product Line Growth: The platform highlights purchasing controls, approval workflows, invoice management, vendor management, spend analytics, and white‑label marketplace capabilities. This expanding feature set indicates ongoing product development aimed at deeper customer usage.

LG Construction + Development
Professional Services • Real Estate • Consulting • Design • PropTech

LG Construction + Development is a premier General Contracting and Development company specializing in Mixed-Use Commercial, Restaurant and Retail, Custom Homes, and Sustainable Design services. It is a full-service real estate development, construction, and design firm.

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LG Construction + Development
SitusAMC
Real Estate • Financial Services • PropTech
25 Offices
4,472 Employees
5 Benefits Hiring Now
We're helping our clients identify and capture opportunities across the entire lifecycle of their real estate activity.

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. ...

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SitusAMC

SitusAMC's Top Stability & Growth Strengths

Strong Market Position & Advantage: Market leadership is evident in multiple No. 1 rankings across U.S. CMBS/SASB/CLO special servicing, dominant MSR valuation scale, and substantial residential due-diligence volumes. Independent evaluations (e.g., Above Average servicer rankings) and industry awards reinforce a defensible position across core verticals.

Market Expansion: Geographic reach is highlighted by securing the top primary servicer role for new European CMBS issuances and handling increasing cross-border transaction activity. A broad global footprint with 25+ offices and service to 1,500+ clients indicates widened market coverage.

Innovation-Driven Growth: Proprietary data, valuation tools, and forecasting platforms are being scaled to meet institutional demand. Recognition such as HousingWire’s Tech100 and continued productization of analytics and technology-enabled services support an innovation-led growth path.

WeWork
Other • PropTech
83 Offices
6,813 Employees
38 Benefits

Whether you’re an established enterprise or a growing startup, discover flexible spaces and solutions to move your business forward with WeWork. Welcome to the workplace of tomorrow.

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WeWork
29th Street Capital
Professional Services • Real Estate • PropTech
39 Offices
350 Employees

29th Street Capital is a privately held, Chicago-based real estate investment and advisory firm founded in 2009. It acquires, repositions and manages multifamily properties across the U.S., having invested and managed over $2 billion in assets. Through its property-management business it focuses on resident experience, value-add renovations, disciplined operations and technology-enabled services to improve asset performance and investor returns.

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29th Street Capital
Airbnb
Real Estate • Travel • PropTech
22 Offices
14,622 Employees
38 Benefits Hiring Now

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...

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Airbnb

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.

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AIR Communities
Real Estate • Retail • Sales • Analytics • Hospitality • PropTech
57 Offices
775 Employees
45 Benefits
Apartment Income REIT Corp., known as AIR Communities, is the owner and operator of best-in-class apartment communities.

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...

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AIR Communities

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.

ReloShare
Real Estate • Software • Hospitality • PropTech
Chicago
50 Employees
30 Benefits
Combining Compassion and Convenience

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...

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ReloShare
VTS
Productivity • Real Estate • Software • PropTech • Big Data Analytics
5 Offices
200 Employees
39 Benefits
We are changing the way that Commercial Real Estate operates on a day to day basis. Join us!

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...

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VTS

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.

Flyhomes
Real Estate • PropTech
7 Offices
1,000 Employees
18 Benefits

We’re an end-to-end real estate brokerage and technology company that empowers home buyers, sellers, and agents to win. Flyhomes is transforming the home buying experience through comprehensive consumer education, segmented expertise, financial innovation, and on-demand technology.

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Flyhomes
Gearflow
Artificial Intelligence • Logistics • Productivity • Software • Business Intelligence • PropTech • Industrial
How Modern Fleet Teams Keep Jobs Flowing.

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...

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Gearflow
Obie
Insurance • PropTech
Chicago
125 Employees
13 Benefits Hiring Now
Obie is an insurtech company, hyper-focused on driving value for the modern real estate investor and their partners.

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,...

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Obie
Enodo
Real Estate • PropTech
Chicago

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.

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Enodo
Bozzuto
Real Estate • PropTech
132 Offices
2,832 Employees
26 Benefits
We create sanctuary.

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...

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Bozzuto

Bozzuto's Top Stability & Growth Strengths

Market Expansion: Geographic reach is expanding with new offices, including a Seattle location, and entry into Texas while operating across 22 states. Headquarters relocation to a larger space and growth to 10 corporate offices indicate scaling operations.

Strategic Partnerships: A multifamily investment program with Invesco Real Estate provides approximately $1 billion in investment capacity, already supporting acquisitions in Florida and Northern Virginia. This partnership underpins ongoing capital deployment for targeted multifamily assets.

Strong Market Position & Advantage: National rankings place the company among the top multifamily property managers, supported by awards in development and construction. A large management platform of roughly 150,000 apartments and recognition for resident experience reinforce competitive standing.

Kin Insurance
Fintech • Insurance • PropTech
3 Offices
800 Employees
30 Benefits

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....

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Kin Insurance

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.

Independence Realty Trust, Inc.
Real Estate • PropTech
3 Offices
283 Employees

Independence Realty Trust, Inc. (NYSE: IRT) is a publicly traded real estate investment trust (REIT) that owns and operates multifamily apartment communities across non-gateway U.S. markets. The company's mission is to provide exceptional living experiences for its residents while delivering attractive risk-adjusted returns for its shareholders through diligent portfolio management and strong operational performance.

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Independence Realty Trust, Inc.
Sentral
Real Estate • Sharing Economy • Hospitality • PropTech

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...

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Sentral

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