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Chicago Startups to Watch in 2027: 6 Verified Companies, Their Funding and Lessons for Founders

Chicago Startups to Watch in 2027: Verified Companies in Insurtech, Robotics, Biotech, Logistics and Fintech

Chicago is the Midwest's largest startup city, with strong corporate customers, top universities and investors who like businesses with real revenue. The 2026 version of this article listed ten "top startups", but several were large companies, public companies or no longer independent. For this 2027 edition we checked every company on its own website, newsroom, careers or legal page in October 2026: that it still operates, that it gives a Chicago base, what it sells and what it publishes about its numbers. Funding rounds we found only in the press are named with the outlet. The old names and what happened to them are listed further down.
Quick answer: the Chicago startups to watch in 2027 are Honeycomb (insurance for apartment buildings), Kin (direct-to-consumer home insurance), Formic (factory robots for a fixed monthly price), Evozyne (AI-designed protein drugs), ShipBob (fulfilment for online brands) and M1 (investing with an AI advisor). Tempus AI, G2, ActiveCampaign, MAIA Biotechnology and QuillBot from the old list are now public companies, scale-ups or part of a larger group, and VillageMD and Leap moved out of the list.
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Why Chicago Matters for Founders in 2027

The StartupBlink 2026 ecosystem index ranks Chicago 17th in the world, up 2 places, and 7th in the United States, unchanged since 2025. It counts 2,602 startups in the city and names foodtech as Chicago's leading industry, with software and data, healthtech, fintech and e-commerce among its larger sectors. The old article said Chicago was 15th: that was StartupBlink's 2024 position, so we replaced it with the current index.
Chicago is also a good city for women who build companies. In a 2019 analysis, Startup Genome found that 25% of Chicago's startups had female founders, against a global average of 14.1%. The figure is old, but it explains why the city has many women-focused funds and programmes. Comparing cities? Our guide to the best startup cities in North America ranks Chicago against its rivals, and our lists of Baltimore startups to watch, San Diego startups to watch and Mexico City startups to watch use the same checks.

Chicago Startups to Watch in 2027 Compared

StartupWhat it doesCustomersLatest funding we citeChicago base checked
HoneycombInsurance for apartment buildings, condo and HOA associationsProperty owners, managers, agents$40M, June 2026 (Fortune)Yes, new Chicago HQ (newsroom)
KinDirect-to-consumer home insurance and home financeHomeowners in 14 states$50M Series E, September 2025 (Kin)Yes, Chicago-datelined releases
FormicRobotic automation for factories, paid monthlyMid-market US manufacturers$50M raise, October 2026 (Formic)Yes, Chicagoland HQ (newsroom)
EvozyneProtein drugs designed with generative AIFuture patients, pharma partners$81M Series B, September 2023 (Latham & Watkins)Yes, Chicago, IL (homepage)
ShipBobWarehousing, packing and shipping for online brandsE-commerce brands$200M Series E, June 2021 (TechCrunch)Yes, Chicago address (homepage)
M1Investing, saving, borrowing and AI adviceRetail investorsNone citedYes, Chicago address (homepage)
Sources: each company's official website, newsroom or press release, checked 28 October 2026; other rounds as reported by the outlet named. "None cited" means we found no funding announcement we could link.

The Chicago Startups to Watch in 2027

1. Honeycomb: insurance for apartment buildings

Honeycomb sells real estate insurance to apartment building owners, condo and homeowner associations, landlords, property managers and developers, with an online quote that starts from the property address. Its homepage shows an AM Best "Excellent" rating for financial strength, and its about page names co-founders Itai Ben-Zaken (CEO) and Nimrod Sadot (CTO). The company's newsroom links coverage of its new Chicago headquarters in July 2025, its 20th state (Colorado) in November 2025, and 2026 launches in Oregon, Kansas, Missouri, Nevada, Tennessee and South Carolina. It announced a $36 million Series B in May 2024, led by Zeev Ventures according to TechCrunch, and according to Fortune, investors added $40 million in June 2026 for its no-inspection insurance AI.
Lesson for founders: pick a boring, underserved niche (here, insurance for older apartment buildings) and grow one state at a time, announcing each step.

2. Kin: home insurance sold directly online

Kin sells homeowners, condo, mobile home, landlord, flood and auto insurance directly to consumers, plus mortgages and home equity loans. Its homepage lists 14 states, from Florida and Texas to California and Virginia, and says it is trusted by more than 200,000 customers. In a press release datelined Chicago on 8 September 2025, Kin announced an oversubscribed $50 million Series E at a $2 billion pre-money valuation, together with a $200 million debt facility, of which $145 million repaid an older facility. Its second-quarter 2026 results, also announced from Chicago in August 2026, report continued growth and profitability at Kin Insurance, Inc.
Lesson for founders: a Chicago company does not have to sell in Chicago. Kin built its business around homes exposed to extreme weather, the problem its Series E announcement says it wants to help homeowners adapt to.
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3. Formic: factory robots for a monthly fee

Formic gives mid-market US manufacturers robotic automation as a full service: palletising, case packing, machine tending, pallet wrapping and mobile robots, with "one fixed monthly price" and no upfront capital. Its homepage reports 99.30% uptime over the last 12 months, and its careers section hires in "Chicago + remote U.S." Its newsroom lists a new 53,000-square-foot Chicagoland headquarters opened in June 2026, a $27.4 million raise in June 2024, and a $50 million raise announced on 22 October 2026 to scale what it calls physical AI across American manufacturing.
Lesson for founders: if your customers cannot afford the upfront cost, change the business model. Renting robots turned a capital purchase into a monthly bill.

4. Evozyne: protein drugs designed with AI

Evozyne uses generative AI to design new therapeutic proteins for immune-mediated diseases where current biologics fail too many patients. Its site gives Chicago, IL as its location and names a pipeline of IgG proteases, next-generation cytokines and respiratory disease candidates; it has moved from its earlier broad protein-evolution pitch to drug development. According to Latham & Watkins, which advised NVIDIA's venture arm on the deal, Evozyne raised an $81 million Series B in September 2023 led by Fidelity Management & Research Company and OrbiMed. We found no newer round.
Lesson for founders: deep tech startups narrow their focus as they mature. Evozyne went from "AI for proteins" to specific diseases investors can value.
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5. ShipBob: fulfilment for online brands

ShipBob stores, picks, packs and ships orders for e-commerce brands and handles returns, using a network of more than 50 fulfilment centres that it says it has built and operated in-house since 2014. Its homepage footer gives its address at 120 N Racine Avenue, Chicago. Its press page links TechCrunch's report that ShipBob raised a $200 million Series E in June 2021 at a valuation above $1 billion. We found no newer round.
Lesson for founders: small online sellers want the delivery speed that big marketplaces offer. Selling that speed as a service lets you grow with thousands of brands.

6. M1: investing with an AI advisor

M1 combines investing, saving and borrowing in one app and now promotes M1 Advisor, AI-powered fiduciary advice from its SEC-registered adviser. Its homepage reports more than 400,000 clients and more than $14 billion in client assets as of September 2026, and gives M1 Finance LLC's address at 200 N LaSalle Street, Chicago (member FINRA and SIPC). We found no funding announcement on its site, so we cite none.
Lesson for founders: regulated fintech grows slowly but compounds. Licences, trust and assets under management are a moat that is hard to copy.

Chicago Companies From the Old List: Grown Up or Changed

The 2026 version of this article mixed startups with large, public or acquired companies. They are still worth studying, but they are no longer startups to watch:
  • Tempus AI: the precision medicine company now trades on Nasdaq (TEM). Its second-quarter 2026 results, datelined Chicago, report revenue of $382.5 million, up 22% year on year, and guidance of $1.595 to $1.605 billion for 2026. Tempus also agreed to buy Personalis for about $1.5 billion in enterprise value.
  • G2: the software review marketplace was founded in 2012 by five entrepreneurs. Its about page gives its Chicago headquarters at 100 S. Wacker Drive, $257 million in total funding and more than 200 million annual buyers. It is a scale-up, not an early-stage startup.
  • ActiveCampaign: the marketing automation company was founded in 2003 by Jason VandeBoom, keeps its headquarters in Chicago, is privately held and has more than 150,000 customers in over 170 countries.
  • MAIA Biotechnology: the cancer drug developer is listed on NYSE American (MAIA) and based at 444 West Lake Street, Chicago. Its investor site names ateganosine (THIO) as its lead programme, in a pivotal Phase 3 trial (THIO-104) in non-small cell lung cancer.
  • QuillBot: the AI writing tool started at the University of Illinois' iVenture Accelerator and grew from a small Chicago office, but since 2021 it has been part of Learneo (formerly Course Hero). It reports more than 35 million monthly active writers.
  • VillageMD: a large primary care group backed by Walgreens, not a startup. According to Fierce Healthcare, Walgreens said in 2024 that it was exploring the sale of all or part of VillageMD. We removed it.
  • Leap: the retail-as-a-service company still operates and its site lists 100 active stores and more than 175 brands, but it names no headquarters and lists Chicago as one market next to New York, Los Angeles and Florida. We could not confirm it is still Chicago-based, so it left the main list.
We also removed the old article's unsourced figures ("over 1,600 active startups" and "$3 billion in venture capital"), the outdated "15th globally" rank, and its links to third-party startup lists.

Which Chicago Startup Should You Learn From?

  • You build insurtech or another regulated product: study Honeycomb and Kin, which grow state by state and announce each licence.
  • You sell to factories or industrial buyers: study Formic and its fixed monthly price instead of a large upfront sale.
  • You build deep tech or biotech: study Evozyne, Tempus AI and MAIA, and how long the road from research to revenue is.
  • You build e-commerce services: study ShipBob, which serves online brands instead of competing with them.
  • You build fintech for consumers: study M1 and how it adds AI advice on top of a trusted, regulated core.
  • You build B2B software: study G2 and ActiveCampaign, two Chicago companies that grew for over a decade before getting big.

How Founders Use Chicago's Startup Scene

Chicago founders raise from local funds and from the coasts, so plan your investor list early. Start with our directories of angel investors in North America, early-stage VC firms and VCs for AI startups, and test your pitch at one of the startup competitions in North America. Women founders can add non-dilutive money from our lists of grants for female entrepreneurs and female founder grants.
Still choosing where to build? Compare the best countries for early-stage startups and our startup cities directory. Before you copy any of these business models, validate your startup idea with real customers. When you want to get noticed, list your startup in the F/MS marketing directories, publish your startup press release, and write about your product with the F/MS AI SEO Tool or the AI SEO Blog so customers and AI assistants can find you.
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FAQ About Chicago Startups to Watch in 2027

Which Chicago startups should I watch in 2027?

Our verified list: Honeycomb, Kin, Formic, Evozyne, ShipBob and M1. Each still operates and shows a Chicago base on its official site or in its own press releases, checked in October 2026.

Where does Chicago rank as a startup ecosystem?

StartupBlink's 2026 index ranks Chicago 17th in the world, up 2 places, and 7th in the United States. It counts 2,602 startups in the city and names foodtech as its leading industry.

Which Chicago startups raised money recently?

Formic announced a $50 million raise in October 2026, Honeycomb added $40 million in June 2026 according to Fortune, and Kin raised a $50 million Series E at a $2 billion pre-money valuation in September 2025.

Is Tempus still a Chicago startup?

Tempus AI is still based in Chicago but is now a public company on Nasdaq (TEM), with second-quarter 2026 revenue of $382.5 million. It is a scale-up to learn from rather than a startup.

Is QuillBot a Chicago company?

QuillBot grew from a small Chicago office after the University of Illinois' iVenture Accelerator, but it has been part of Learneo (formerly Course Hero) since 2021.

Which Chicago startups work in insurance?

Honeycomb insures apartment buildings and condo associations, and Kin sells home insurance directly to consumers in 14 states. Both are based in Chicago.

Is Chicago good for women founders?

Startup Genome reported in 2019 that 25% of Chicago's startups had female founders, against a global average of 14.1%. The city also has many women-focused funds and programmes.

What can founders learn from Chicago startups?

Pick an unglamorous niche with real buyers, grow one market at a time, and use business models such as monthly pricing that remove the customer's upfront risk.

Where can I get a backlink by writing about my startup?

You can publish a guest post in one of the Fe/male Switch startup blogs, which rank in Google and in AI tools. Get a quality backlink.

About the Author

Violetta Bonenkamp, also known as MeanCEO, is an experienced startup founder with an impressive educational background including an MBA and four other higher education degrees. She has over 20 years of work experience across multiple countries, including 5 years as a solopreneur and serial entrepreneur. Throughout her startup experience she has applied for multiple startup grants at the EU level, in the Netherlands and Malta, and her startups received quite a few of those. She’s been living, studying and working in many countries around the globe and her extensive multicultural experience has influenced her immensely.
2026-10-28 19:51 Best Startups