Top Insurance Companies in Chicago, IL (166)
PURE is a member-owned insurer designed exclusively for financially successful individuals and families and dedicated to delivering an exceptional experience. We provide customizable coverage for high-value homes, automobiles, jewelry, art, personal liability, watercraft, flood, fraud and cyber fraud, and we aim to alleviate stress, solve challenges and remove conflict from the insurance process wherever possible for our members.
Founded in 1985, IFG Companies is one of the largest privately held insurance groups in the United States. IFG provides property-casualty insurance on both a non-admitted and an admitted basis. IFG has two principal segments of business, our Bind Division and our Brokerage Division. Bind Division Offers liability and property coverage for smaller businesses and other entities written through a national network of...
When is a comprehensive, AI-driven technology platform and healthcare severance solution that provides unparalleled support for employees navigating offboarding, life changes, and the complex health insurance market, all while saving your company time and money.
When (forwhen)'s Top Stability & Growth Strengths
Investor Backing & Capital Strength: The company raised a $4.6M seed round in 2024, bringing total funding to about $7M, signaling investor confidence. Capital is earmarked to expand its AI-driven platform, add services, and grow distribution.
Strategic Partnerships: The platform powers isolved’s Portable Alternative Coverage program and has added institutional relationships such as a university partnership, extending reach through established channels. Extensive HRIS integrations further support scalable distribution and adoption.
Innovation-Driven Growth: An AI-powered offboarding and benefits marketplace is being expanded with new services including Medicare transitions and post-employment tools. This product strategy targets an underserved niche around COBRA alternatives and transition support.
Paramount Loss Consulting is a public adjuster that represents policyholders & negotiates with insurance companies for the best property loss claim amount.
Arlo is rebuilding health insurance for small businesses from first principles. We use AI across underwriting, clinical programs, operations, and member experience to make sure as much of every premium dollar as possible goes to actual care, and to build an insurer that gets smarter and more efficient over time.
BriteCo provides an innovative cloud-based Appraisal Management System for jewelers to create, track and manage appraisals saving time and effort. Once appraised, BriteCo sends an insurance quote directly to the customer via text or email to get immediate coverage backed by an A.M. Best A rated global reinsurance carrier.
With elite insurance expertise empowered by breakthrough technology, Newfront is the modern insurance brokerage for the 21st century. With hundreds of veteran brokers and dedicated service professionals, we combine domain expertise with data-driven market intelligence to support our clients.
Newfront's Top Stability & Growth Strengths
Strong Revenue Growth: Organic revenue expanded steadily over multiple years, and industry rankings placed the firm among the Top 40 U.S. brokers by revenue. Evidence suggests continued momentum with reported gains in 2024 U.S. brokerage revenue and improved national standing.
Investor Backing & Capital Strength: The company secured substantial funding and achieved a multibillion-dollar valuation, signaling strong external capital support. Its sale to WTW for a transaction value up to the low billions further underscores recognized value and access to resources.
Innovation-Driven Growth: The firm differentiates through proprietary, AI-enabled technology that streamlines broking and benefits workflows. Awards and the acquirer’s stated rationale point to technology as a core driver of expansion and competitive advantage.
HealthJoy is driven to remove the complexity from being healthy and well through our app. We guide our members to affordable, high-quality healthcare by consolidating our customers’ health and wellness strategies into a simple, unified digital experience.
HealthJoy's Top Stability & Growth Strengths
Market Expansion: Public milestones indicate the client base grew from ~1,000 employers in 2022 to 1,500+ in 2024 and about 1,800 by April 2025, with covered lives rising past 1M by 2024–2025. Disclosed step‑ups since 2020 suggest durable, not episodic, expansion.
Innovation-Driven Growth: Ongoing launches—new web experience (Jan 2025), generative AI enhancements to JOY, MSK and surgery programs, and GLP‑1 affordability—signal active investment to meet emerging employer cost pressures. These additions position the platform as a unified front door that drives engagement and utilization.
Strategic Partnerships: Partnerships with TPAs/brokers and integrations (e.g., Teladoc, Mark Cuban Cost Plus Drug Company, CareValidate, Springbuk, SurgeryPlus, Employee Navigator) broaden distribution and capability breadth. This channel‑led approach is cited as an edge in mid‑market deployments where employers want a single benefits front door.
At Risk Strategies, part of the Brown & Brown team, we help our clients protect those things that matter most to them. We help them see the way forward in a complex world with specialty insight, practical advice, and custom insurance with a vast network of specialists in Property & Casualty, Employee Benefits, Private Client, as well as Consulting Services...
Risk Strategies's Top Stability & Growth Strengths
Strong Market Position & Advantage: Industry league tables place the Accession platform (Risk Strategies and One80) in the top tier of U.S. brokers by brokerage revenue, supporting the view that the business holds meaningful scale and competitiveness in its core markets.
Strong Revenue Growth: Reported figures describe a sustained upward revenue trajectory across multiple years, including pro forma growth through 2024 and earlier step-ups attributed to a mix of organic expansion and acquisitions.
Investor Backing & Capital Strength: Ownership under Brown & Brown following the acquisition of Accession is positioned as providing a larger platform, added resources, and broader market access that can support continued expansion and resilience.
Honeycomb was built to disrupt the real estate insurance industry. Using Artificial Intelligence and computer vision, we offer apartment buildings, condominium associations and single-family rental dwellings perfectly customized policies at unbeatable rates. Our digitally-native platform makes purchasing insurance an easy and transparent process for property owners, property managers associations directors, and retail agents.
Honeycomb Insurance's Top Stability & Growth Strengths
Strong Revenue Growth: The company is described as growing quickly, including claims of more than doubling sales in 2024 and scaling premium volume from a roughly $130M 2024 run-rate to about $275M annualized by late 2025.
Market Expansion: Operations are described as expanding state-by-state from the high teens toward the low 20s, with multiple new state launches cited through 2024–2026 and stated plans to reach roughly 23 states.
Strategic Partnerships: Added capacity support is described through carrier partnerships and program buildout, including expanding admitted capacity via Trisura and broadening non-admitted offerings with higher per-location limits.
Hartford Steam Boiler (HSB), a proud part of Munich Re, is a leading engineering and technical risk insurer providing equipment breakdown and other specialty coverages, inspection services and engineering consulting. HSB provides clients with risk solutions tailored to their needs and strategies to optimize the reliability, lifespan and efficiency of their equipment and operations.
The Federal Deposit Insurance Corporation (FDIC) preserves and promotes public confidence in the U.S. financial system by insuring deposits in banks and thrift institutions for at least $250,000; by identifying, monitoring and addressing risks to the deposit insurance funds; and by limiting the effect on the economy and the financial system when a bank or thrift institution fails. For policies...
Duck Creek Technologies is a leading provider of core system solutions and professional services to the P&C and General Insurance industry. All of our functionally rich solutions are available via Duck Creek On Demand, our enterprise SaaS solution.
Duck Creek Technologies's Top Stability & Growth Strengths
Strong Market Position & Advantage: Gartner has repeatedly positioned Duck Creek as a Leader in SaaS P&C Core Platforms (North America) across 2024 and 2025, indicating strong competitive standing on vision and execution. The company is frequently described as a top-tier shortlist vendor alongside other leading suites in its segment.
Innovation-Driven Growth: The platform emphasis on evergreen SaaS delivery, low-code configuration, and the integration of AI/ML (including GenAI initiatives with Microsoft) signals an active push to modernize insurer workflows. New products like Duck Creek Clarity and Payments, plus expanded analytics and loss control capabilities, reinforce a steady cadence of platform enhancement.
Strategic Partnerships: A large integration ecosystem (numerous partner integrations and thousands of APIs) and distribution/implementation support via major cloud and SI channels (e.g., Azure marketplace, large integrators) indicate broad partner leverage. This partner depth supports scalability of implementations and expansion into adjacent capabilities via ecosystem connectivity.
Chubb is the world’s largest publicly traded property and casualty insurance company. With operations in 54 countries and territories, Chubb provides commercial and personal property and casualty insurance, personal accident and supplemental health insurance, reinsurance and life insurance to a diverse group of clients. As an underwriting company, we assess, assume and manage risk with insight and discipline. We service...
Old Republic International (ORI) is one of the nation's 50 largest shareholder-owned insurance businesses and traces its beginnings to 1923. We are a member of the Fortune 500 listing of America’s largest companies. ORI’s performance reflects an entrepreneurial spirit, a long-term focus, and a corporate culture that promotes accountability and encourages the taking of prudent business risks. Our subsidiaries actively market,...
Convr is the leading Artificial Intelligence (AI) company that is digitally transforming commercial P&C underwriting. Convr’s d3 Underwriting™ solution uses data discovery and decision science to empower commercial carriers to achieve underwriting and operational excellence through digitizes submission paperwork, such as ACORD applications and loss runs reducing manual data entry, provides insights on risks from thousands of data sources, uses machine...
Sammons® Financial Group Companies (collectively, Sammons Financial Group) provide today’s most sought after life insurance, annuity, and retirement products. At Sammons Financial Group, we hire people who think like owners because we are a privately held company owned by an Employee Stock Ownership Plan. We own our unique values-based culture, we own our spirit of excellence, and we own our...
Life is about more than just money. That’s why Transamerica is committed to helping people make the wealth and health connection—it’s a whole new way of looking at everything that can affect your finances and how the little steps we take today can have a big impact tomorrow. We know that helping people achieve financial security today goes beyond that....
Transamerica's Top Stability & Growth Strengths
Investor Backing & Capital Strength: Disclosures indicate the company’s U.S. insurance entities are viewed as financially sound and supported by a well-capitalized parent, reinforcing claims-paying confidence. This foundation underpins distribution credibility in core markets.
Product Line Growth: Recent launches in annuities and ETFs, alongside strong traction in key life products, point to an expanding and commercially active lineup. Feedback suggests this breadth is helping drive new sales in target channels.
Future-Ready Strategy: Management is repositioning around a U.S.-centric identity, investing in distribution, and de-risking legacy blocks to free capital for growth. Stated targets and brand updates signal an intent to gain share in life and retirement.
A multi-year winner of Best Places to Work in Insurance (2009-2025), Hylant is a full-service insurance brokerage with offices in Florida, Georgia, Illinois, Indiana, Michigan, Ohio and Tennessee with more than 1,000 professionals on staff. Hylant offers complete risk management services, employee benefits consultation, wellness strategies, loss control, healthcare management and a wide array of insurance solutions for both businesses...
Hylant's Top Stability & Growth Strengths
Market Expansion: Evidence indicates sustained geographic expansion via new offices, acquisitions, and international partnerships across multiple regions. Openings in markets like Indiana, Miami, and Birmingham (MI), along with a Mexico presence and a Hawaii partnership, signal ongoing footprint growth.
Strong Revenue Growth: Evidence suggests multi-year organic growth and rising top-line momentum, alongside ambitions to scale materially over the next decade. Multiple statements in the data cite increased revenue levels and sales velocity, even though precise audited figures are not disclosed.
Strong Hiring & Retention: Feedback suggests durable employer-of-choice standing, with many consecutive Best Place to Work in Insurance recognitions. Coupled with workforce expansion and leadership additions, this supports sustained talent attraction and retention capacity.
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.
