chicago-startup
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FoodBoss Built Kayak for Takeout - Then Google Walked Into the Kitchen
The Chicago startup made delivery apps compete on price and speed, then learned the harder lesson of comparison businesses: the better your idea works, the more likely a platform giant is to copy the view.
The Chicago Startup That Wants to Make Waiting for Money Feel as Weird as Waiting for a Fax
Daniel Lev and Benjamin Meeder built a payment layer on stablecoins instead of the batch files banks still run on. Two years in, Pantera wrote a $25M check and revenue is up 23x.
The Startup That Turned the Office Supply Closet Into Software
Kathryn Madden built OfficeLuv around a boring truth: someone always ends up ordering the paper towels. Her bet was that the someone should be software - plus a person who shows up.
The Startup That Turned Dinner Into a Barcode
A smart oven, a weekly box of meals, and one deceptively simple idea: let a barcode do the cooking. Here is how a University of Chicago class project shipped 40 million dinners.
The Chicago lab teaching hospitals to read your blood before sepsis reads you
Sepsis kills more Americans than all cancers combined and hides in plain sight. Prenosis spent a decade building a biobank and an algorithm to catch it in the first 24 hours - and got the FDA to say yes.
The Borrowed Cadillac That Became an Office-Pantry Empire
Crafty began with four friends, a borrowed Cadillac, and a plan to put a kegerator in every office. A decade later it stocks the snacks for DraftKings and Robinhood - and turns the break room into a spreadsheet.
The Yellowstone Microbe That Wants Your Breakfast Table
A geomicrobiologist scooped a strange fungus out of a Yellowstone hot spring. A decade and half a billion dollars later, it is being sold as cream cheese, yogurt and breakfast patties.
CoinFlip
It started with one machine in a Chicago restaurant and no outside money. A decade later CoinFlip runs the world's largest crypto ATM network - and it built the whole thing before anyone offered to fund it.
Paro
Paro is a Chicago-based, AI-powered marketplace that connects businesses and accounting firms with vetted fractional finance and accounting experts - from bookkeepers and controllers to fractional CFOs. Founded in 2015, it pairs its proprietary matching algorithms across 60+ industries and 250+ skill sets with data tools and advisory insight, aiming to become the go-to resource for finance and accounting solutions as the profession faces a deepening talent shortage.
Amper Technologies
Amper Technologies is a Chicago-based industrial IoT company that helps manufacturers see and improve what happens on their shop floors in real time. Its FactoryOS platform pairs non-invasive sensors that clip onto any machine - regardless of age or brand and install in about ten minutes - with AI-driven analytics that track machine utilization, OEE, downtime, labor and job performance. Founded in 2016, Amper turns legacy factory equipment into a source of live production data without expensive retrofits or complex IT integrations, and was acquired by ECI Software Solutions in December 2025.
Benji
Benji is the universal API for loyalty partnerships - think 'Plaid for loyalty rewards.' It lets brands across travel, hospitality, retail, food and fintech connect their loyalty programs through a single integration, launching co-branded earn, redemption, transfer and co-acquisition campaigns in days instead of months. Founded by the serial team behind 2ndKitchen (acquired by REEF Technology in 2021), Benji raised a $6.25M seed round in 2026 and already powers a network of programs - including JetBlue, CookUnity, 1-800-Flowers and Chip City - representing more than 50 million combined active members.
Classkick
Classkick is a Chicago-based education technology company that makes a digital formative-assessment platform where teachers watch students work in real time and give instant feedback. Founded by former Teach for America math teacher and ex-Google/YouTube engineer Andrew Rowland, the tool lets teachers build or import interactive assignments, draw directly on each student's canvas, drop reusable feedback stickers, and auto-grade multiple-choice and fill-in-the-blank answers. Students can raise a virtual hand for help - even anonymously - and ask peers. Used by more than 10 million users across all 50 U.S. states and dozens of countries, Classkick's pitch is simple: more tries for kids every day, and less grading busywork for teachers.
Marketplace.city
Marketplace.city is a Chicago-based govtech company that helps state and local governments source, validate, and procure technology. Its Clearbox platform turns a repository of historical vendor, contract, and pricing data into managed procurement services (Clearbox Procure) and a research subscription (Clearbox Source), aiming to compress technology buying cycles that once ran months or years down to roughly 100 days. Founded out of a 2016 collaboration with New York City's Mayor's Office of Technology and Innovation, the company has supported over 200 governments.
Out of Office
Out of Office (OOO) is a Chicago-based travel technology company that helps people plan trips using recommendations from the people they actually trust - friends, family, and the influencers they follow - instead of anonymous review sites. Founded in 2020 by former Trunk Club executives Jan Seale and Coabi Kastan, the app lets travelers browse curated spots across thousands of cities, build and share itineraries, book hotels, and reserve restaurant tables in one place, and more recently generate full trip plans with an AI trip generator.
Parallel Works
Parallel Works is a Chicago-based software company, spun out of Argonne National Laboratory in 2015, that builds ACTIVATE - a hybrid multi-cloud control plane for high-performance computing and AI. The platform gives researchers, engineers and defense teams a single interface to provision, orchestrate and share compute across on-premises clusters and the major clouds (AWS, Azure, Google Cloud, Oracle), with built-in cost governance, role-based access and security controls. In 2025 ACTIVATE's High Security Platform became the first hybrid multi-cloud solution to earn a U.S. Department of Defense IL5 Authority to Operate.
Power Kiosk
Power Kiosk is a Chicago-based SaaS company that runs a cloud-based marketplace connecting retail energy suppliers with the brokers and consultants who buy electricity and natural gas on behalf of businesses. Founded by Northwestern Ph.D. Hamed Babai, the platform pulls fragmented supplier rates, contracts, and market data into one AI-assisted workflow so brokers can quote, compare, and close deals in minutes instead of days. The company says it has managed 16,000+ customers across 34 states and provinces and returned roughly $120 million in savings.
Quantum Rise
Quantum Rise is a Chicago-based AI transformation company founded in 2024 by serial entrepreneur Alex Kelleher. It sells what it calls 'Consulting 2.0' - a products-not-projects model that pairs an enterprise AI operating system (QR/OS), a repeatable methodology, and forward-deployed experts to help mid-market and enterprise clients turn AI into measurable revenue and cost savings. Backed by a $15M seed round from Erie Street Growth Partners, the company argues the traditional billable-hours consulting model is about to collapse under automation, and it aims to fill the gap between the Big Four giants and smaller boutique shops.
Qumis
Qumis is a Chicago-based insurtech building attorney-trained AI for commercial insurance. Its coverage intelligence platform reads dense property and casualty policies the way a seasoned coverage attorney would - comparing quotes and endorsements, flagging gaps across policy towers, and backing every answer with source-linked citations and transparent reasoning. Founded by a former coverage attorney and a former Goldman Sachs engineering leader, Qumis already serves five of the 15 largest U.S. brokers, along with specialty carriers and insurance law firms, and has raised $6.75M to put a coverage specialist at every desk.
Cardiosense
Cardiosense is a Chicago-based health-tech company building an AI platform that turns raw physiological signals into clinical intelligence for heart failure. Its FDA-cleared CardioTag wearable simultaneously captures ECG, PPG and seismocardiogram (SCG) signals, and its machine-learning algorithms estimate pulmonary capillary wedge pressure (PCWP) - a key measure of cardiac filling pressure - noninvasively, so clinicians can spot a worsening heart before it lands a patient in the hospital.
DubClub
DubClub is a Chicago-based platform where sports bettors find, follow, and subscribe to vetted handicappers ("cappers") for premium picks and analysis delivered by text, email, and Discord. It gives creators the tools to monetize their betting content - payments, subscriber messaging, and community - while giving amateur bettors one trustworthy place to access expert plays. Backed by a $7.5M Series A led by Renegade Partners, DubClub's tagline is "Win More Together."
Letter AI
Letter AI is an AI-native revenue enablement platform that turns a company's existing knowledge into real-time, deal-specific guidance for sales, customer success, and sales engineering teams. Founded in 2023 by Ali Akhtar and Armen Forget and backed by Y Combinator, the Chicago-based company combines content, coaching, training, and live CRM data into one workflow. In February 2026 it raised a $40M Series B led by Battery Ventures to power its new deal-level product, Letter Compass.
ModelOp
ModelOp is a Chicago-based enterprise software company that builds AI governance and lifecycle automation software. Its flagship platform, ModelOp Center, acts as a centralized system of record and 'control tower' for all of an organization's AI - traditional machine learning, generative AI, agentic AI, and third-party tools - letting enterprises inventory every model, automate approvals and testing, enforce policy, monitor production systems for drift and risk, and produce audit-ready documentation. The company sells primarily to large, regulated enterprises such as financial services, healthcare, and government, and counts Fortune 500 names among its customers.
Renterra
Renterra is a Chicago-based software company building a modern, AI-powered operating system for the equipment rental industry. Founded in 2022 by Andy Feis and Nick Hibberd, the cloud platform unifies inventory, contracts, online booking, payments, maintenance, and reporting for heavy equipment rental businesses across the US and Canada. It has raised $16M total, including a $9M Series A led by Avenue Growth Partners in January 2026, and serves hundreds of rental companies managing hundreds of millions in annual rental transactions.
HealthJoy
HealthJoy is a Chicago-based digital health company that turns the tangle of employer-sponsored benefits into a single app. Its AI concierge, JOY, plus a team of human healthcare advocates, guides employees to the right care - from telemedicine and virtual primary care to MSK therapy, behavioral health, prescription savings and medical bill review - while helping employers cut healthcare spend. Founded in 2014, HealthJoy serves more than 1,800 employers and over 1.25 million members.
NovaScan
NovaScan is a Chicago-based clinical-stage oncology company building low-cost, point-of-care devices that detect cancer in real time. Its platform pairs spectral bioimpedance with machine learning around a single biophysical signal - the Cole relaxation frequency, which differs by orders of magnitude between cancerous and healthy tissue. Two lead products, nsCanary for assessing biopsy cores and MarginScan for checking surgical excision margins, aim to deliver answers in seconds instead of the days that conventional pathology can take.
Trajektory
Trajektory is a Chicago-based sponsorship intelligence platform that helps teams, leagues, brands, and agencies measure the value of every sponsorship asset - digital and non-digital - in one place. Using AI logo detection and data aggregation across broadcast, streaming, social, in-venue signage, email, web, and mobile, it turns months of manual recap work into real-time, auditable reporting. The platform tracks more than $180 billion in annual sponsorship value and works with roughly half of major North American pro teams.