Best InsurTech Companies in Chicago, United States
The 65 best InsurTech companies in Chicago, United States in 2026, ranked by funding and momentum. Funding, investors, founders, valuation, tech stack and live signals. Top: Clearcover.
Our analysis of 50 InsurTech companies
$13.8b in tracked funding; 100% of the stack-profiled cohort runs cloud-native; funding activity peaked in 2025.
Ranked: Best InsurTech companies in Chicago
| # | Company | Disclosed funding | Last round | Employees | Founder | Tech stack | Web popularity | Patents & IP focus | Recent signals |
|---|---|---|---|---|---|---|---|---|---|
| 1 | Clearcover 🦄 Online platform that provides automotive insurance 78Funding top 15%Tech top 22%Moat top 26%Customers top 28% All 12 signals ▾Fundingtop 15% Techtop 22% Moattop 26% Customerstop 28% Producttop 31% Innovationtop 37% Markettop 38% Talenttop 38% AItop 45% Growthbottom 45% Globalbottom 37% Newsbottom 24% Funding: Raised $406M across 9 rounds · 9 rounds over 10 yrs (0.9/yr) Tech: 60 technologies across 7/8 capability areas · Cloud: Amazon Cloudfront, Amazon S3 rank vs industry peers · Fliar Intelligence Index 78/100 | $406M | 8 mo ago | 450 | Derek Brigham Co-Founder & Chief Operating Officer | SentryZendeskApple iCloud Mail+33 | Top 5M | — | — |
| 2 | Kin 🦄 Online platform for homeowner insurances for individuals 69Funding top 12%Product top 21%Moat top 26%Tech top 32% All 10 signals ▾Fundingtop 12% Producttop 21% Moattop 26% Techtop 32% Markettop 34% Innovationtop 39% Talentbottom 49% Growthbottom 47% Globalbottom 39% Newsbottom 27% Funding: Raised $372M across 13 rounds · 13 rounds over 9 yrs (1.4/yr) Product: 7 distinct product lines · Company stage: Series E rank vs industry peers · Fliar Intelligence Index 69/100 | $372M | 9 mo ago | 504 | Sean Harper CEO and Co Founder | Apple iCloud MailGoogle WorkspaceTypeScript+28 | Top 1M | — | 1 job opening · 1 award |
| 3 | Snapsheet Cloud-based software for auto insurance claim management | $103M | 35 mo ago | 199 199 → 488 (+145%) | Brad Weisberg Co-Founder & CEO | WordPressVisual ComposerMySQL+30 | Top 5M | — | 1 award |
| 4 | Maestro Health AI-powered TPA optimizing self-funded health plans for cost savings | $59M | 116 mo ago | 246 | — | VuetifyAmazon ALBVue.js+10 | Top 10M | — | — |
| 5 | GoHealth Platform offering healthcare insurance solutions | $50M | 44 mo ago | 2,467 2,467 → 2,006 (-19%) | Clint Jones Co-Founder & Co-Chairman | DrupalApple iCloud MailPHP+33 | Top 100k | — | 2 launchs |
| 6 | HDVI Telematics-based data & monitoring solutions for auto insurers and fleet owners | $48M | 16 mo ago | 82 | Reid Spitz President & Co-Founder | WordPressMySQLPHP+30 | Top 50M | — | — |
| 7 | Arturo Analytics solutions for investment and research industries | $47M | 33 mo ago | 59 | Marty Smuin Chief Executive Officer | WebflowApple iCloud MailGoogle Workspace+20 | Top 50M | — | — |
| 8 | Obie Insurance solutions for landlords and real estate investors | $40M | 39 mo ago | 110 | Ryan Letzeiser Co-Founder & CEO | WebflowApple iCloud MailGoogle Workspace+23 | Top 5M | — | — |
| 9 | Insureon Online comparison platform for property & causality insurance | $31M | 128 mo ago | 115 115 → 133 (+16%) | — | SitecoreSentryYouTube+16 | Top 1M | — | 1 award |
| 10 | Aclaimant Provider of enterprise incident management system | $30M | 41 mo ago | 46 | Joel Friedman Founder and CTO | HubSpot CMS HubApple iCloud MailGoogle Workspace+24 | Top 10M | — | — |
| 11 | Figo Pet Insurance Flexible pet insurance designed by pet people for modern pet parents | $22M | 78 mo ago | 138 | — | Amazon WebstoreContentfulNode.js+38 | Top 500k | — | — |
| 12 | CCC AI and cloud-driven insurance claims solution for the insurance and automotive industry | $14M | 74 mo ago | 6 | — | WebflowMarkerApple iCloud Mail+28 | Top 500k | 3 patents Passive dust suppression systems for bulk material transfer chutes and conveyors | — |
| 13 | DAIS Insurance policy management solutions for insurance distributors | $14M | 94 mo ago | 22 | Milos Dedovic Founder & COO | WordPressMySQLPHP+17 | Top 10M | — | — |
| 14 | ConnectedHealth Benefits shopping marketplace for employees | $8M | 139 mo ago | 97 | — | — | — | — | — |
| 15 | WatchTower Quoting software for insurance industry | $8M | 69 mo ago | 85 | Ryan Sachtjen Co-Founder | — | — | — | — |
| 16 | When Insurance Provider of health insurance services for employees | $7M | 6 mo ago | 8 | — | SentryZendeskApple iCloud Mail+18 | Top 50M | — | — |
| 17 | Qumis AI-powered insurance policy review platform | $7M | 6 mo ago | — | Dan Schuleman Co-Founder & CEO | — | — | — | — |
| 18 | Prima Solutions Provider of a software suite for the insurance industry | $6M | 177 mo ago | 186 | — | WordPressMySQLPHP+25 | Top 10M | — | — |
| 19 | FlexMinder Healthcare reimbursement automation | $3M | 147 mo ago | 374 | — | — | — | — | — |
| 20 | Vikaran Solutions Tech solutions for Workers Comp and Commercial Insurance | $1M | 185 mo ago | — | Rick Madock ex-CEO | — | — | — | — |
| 21 | MessageControl Email security and anti-spymail solution | $1M | — | 16 | Paul Everton Founder | — | — | — | — |
| 22 | Dispute Bills Medical bills claim management for consumers | $400K | 124 mo ago | 3 | — | — | — | — | — |
Top 12 InsurTech companies in Chicago
#1
Series D · Chicago, Illinois · founded 2016 · 450 employees$406Mraised▾
Online platform that provides automotive insurance. It features a Quick View ID card to manage policy information, submit claims, claims to track, change payment methods, make payments, view payment information, and more. It also validates coverages and determines eligibility for expedited payment.
- Oct 2025Series D$25M
- Jan 2025Series D$26.2M
- Oct 2024Series D$44M
- Mar 2024Series D$55M
#2
Kin 🦄Series E · Chicago, Illinois · founded 2016 · 504 employees$372.4Mraised▾
Online platform for homeowner insurance platform for individuals. It offers claims settlement services. It features a repair program for policyholders to rebuild homes. It offers insurance such as condo insurance, vacation home insurance, landlord insurance, and more. It also helps with insurance fraud.
- Sep 2025Series E$50M
- Sep 2025Conventional Debt$200M
- Jan 2024Series D$15M
- Sep 2023Series D$33M
#3
Series A · Chicago, Illinois · founded 2020 · 8 employees$7Mraised▾
Provider of health insurance services for employees. It offers health and financial wellness insurance services for individuals and families. Its employees can view their benefit amount and get answers to common health insurance questions on the platform. It provides services to the employees after a job loss with their COBRA continuation plan.
- Dec 2025Series A$10.2M
- Apr 2025Seed$50K
- Jun 2024Seed$4.6M
- 2023Seed$2.4M
#4
Seed · Chicago, Illinois · founded 2022$6.8Mraised▾
AI-powered insurance policy review platform. It is an AI-powered knowledge platform built by insurance coverage experts to revolutionize insurance policy review and analysis.
- Nov 2025Seed$4.3M
- Dec 2024Seed$2.5M
#5
Series C · Chicago, Illinois · founded 2018 · 82 employees$48.5Mraised▾
HDVI provides telematics-based data & monitoring solutions for auto insurers and fleet owners. It offers solutions for fatigue analysis, compliance management, analyzing driving behavior, vehicle-related data management, and more. It also offers solutions for fleet management.
- Feb 2025Series C$40M
- Aug 2021Series B$32.5M
- Aug 2020Series A$16M
#6
Series E · Chicago, Illinois · founded 2011 · 199 employees$103.3Mraised▾
Snapsheet provides cloud-based software for auto insurance claim management. It facilitates pre and post-claim process along with the underwriting, tracking, validation, auditing and expense management. It provides AI-based automated products- appraisal, transactions, rental & asset management platform and software platform. It also offers a digital payment solution for claims disbursements.
- Jul 2023Series E$5M
- Mar 2021Series E$30M
- May 2019Series E$29M
- Jun 2017Series D$12M
#7
Series B · Chicago, Illinois · founded 2017 · 59 employees$46.7Mraised▾
Arturo provides analytics solutions for investment and research industries. It allows users to analyze data and capture insights from the data and build predictive models to understand business performance. It also offers solutions based on predictive analytics for claims management, insurance quoting, insurance renewals, insurance underwriting, risk modeling, and more. The clients include BRANCH, canopius, hippo, etc.
- Sep 2023Series B$13.7M
- Apr 2021Series B$25M
- Feb 2020Series A$8M
#8
Acquired · Chicago, Illinois · founded 2014 · 110 employees$39.6Mraised▾
Insurance solutions for landlords and real estate investors. It offers coverage for rental properties and support customers understand the natural risks in their area through their risk map feature.
- Mar 2023Series B$26M
- May 2021Series A$10.7M
- Feb 2020Seed$2.8M
- Aug 2019Seed$150K
#9
Series B · Chicago, Illinois · founded 2009 · 46 employees$30.5Mraised▾
Provider of enterprise incident management system. It provides a mobile app, web portal, and personal incident hotline to manage incidents and claims. It captures actionable information, customizes incident reporting, and engages with every employee. Its organizations can report all incidents personal, property, and near-hit incidents also.
- Jan 2023Series B$2.5M
- Apr 2021Conventional Debt—
- Mar 2021Series B$15M
- Feb 2021Series A$50K
#10
Public · Chicago, Illinois · founded 2001 · 2467 employees$50Mraised▾
Platform offering healthcare insurance solutions. It provides healthcare insurance solutions for insurers, agents, and consumers. It features solutions for sales, comparison, lead management, CRM, and more. It also offers health and dental policy solutions for individuals and families.
- Sep 2022Post IPO$50M
- Jun 2012Series C$50M
- 2004Conventional Debt—
#11
Acquired · Chicago, Illinois · founded 2012 · 138 employees$21.5Mraised▾
Flexible pet insurance designed by pet people for modern pet parents. They offer customizable pet insurance plans with options for wellness coverage, vet exam fee coverage, and curable pre-existing conditions. They focus on simplicity, transparency, passion, inclusivity, flexibility, and community. They provide fast claim processing, often within three business days, and offer access to licensed veterinary professionals. Their platform includes a pet cloud, blog, and resources to support pet parents. They are committed to providing pet insurance that fits into the lives of pet parents, offering a range of options to meet individual needs. They are a remote-friendly company with a pet-friendly office. They are pet-forward insurance experts, with a US-based customer experience team that is P&C licensed. They offer pricing and subscription options.
- Dec 2019Series C$5M
- Jan 2019Conventional Debt—
- Jan 2019Series B$1.5M
- Mar 2018Series B$4M
#12
Acquired · Chicago, Illinois · founded 2013 · 246 employees$59Mraised▾
AI-powered TPA optimizing self-funded health plans for cost savings. It is a technology-driven third-party administrator specializing in transforming healthcare for self-funded employer health plans. It leverages machine learning and deep learning to streamline operations, uncover savings, and maximize health outcomes. The company provides access to provider networks, claims processing, plan design, cost containment, compliance, and actionable analytics. It offers proactive member services, guiding members to quality care and value-based clinical solutions. The company's solutions include pharmacy benefits management, out-of-network repricing, and a medical shopping tool. It caters to small employers with tailored plans, offering user-friendly administration and cost savings. The platform offers member portal and app for digital access to health plan information. The company focuses on empowering healthier lives and redefining cost containment through technology and personalized care.
- Oct 2016Series D$59M
Funding & investor landscape
Notable founders
Market landscape — 10 sub-themes by coverage
Share of InsurTech coverage by sub-theme.
Regulatory-risk over time rising
Funding & growth over time
funding rising · growth rising
How research on Insurtech is moving in the United States
A read on the academic research around Insurtech — which themes are gaining ground, the institutions and researchers driving them, and how the tone is shifting. Based on 22 United States-affiliated papers.
- New York Life Insurance Company2
- Film Independent2
- University of Management and Technology2
- AAA Foundation for Traffic Safety1
- Temple University1
- Conceptual model1
- Conceptual framework1
- Marketing1
- Knowledge management1
- Originality1
- Actuarial science2
- Telematics1
- Incentive1
- Poison control1
- Baseline (sea)1
- Position (finance)1
- Geopolitics1
- Insurance law1
- European union1
- Index (typography)1
Who's filing insurtech patents in the United States
United States insurtech patent filing is steady — 15 filings from 7 assignees (2018–2025), led by State FARM Mutual Automobile Ins, Grunfeld ERIC, Allstate Insurance; annual filings 1→1.
- State FARM Mutual Automobile Ins6
- Grunfeld ERIC5
- Allstate Insurance4
- Clover Health3
- Fiete Stephen2
- Cripe Frederick F2
- American Family Mutual Insurance1
Common questions
Rohit lives in the feed. He covers what's moving right now — the funding rounds, launches and shifts breaking across the trade press — and ties them back to where the sector is heading.