15 Startup Companies in Chicago Making a Name for Themselves

Article by
Michał Rejman
8 min read

Remember our analysis of 15 fast-growing Denver startups? The tech scene in the Colorado capital is booming, but Chicago isn’t too far behind. 

According to the Center for an Urban Future’s report, Chicago has seen some of the fastest startup growth in the U.S. in the last decade, outpacing Seattle, Atlanta, Austin and Denver alike. The tech community is spreading across the Windy City, and today, we’re going to examine 15 hottest startups in Chicago that are leading the trend.

1. dscout

As Steve Jobs famously said, the goal of all companies should be to “Get closer than ever to your customers. So close that you tell them what they need well before they realize it themselves.” Dscout makes it easier than ever before. 

The company’s SaaS platform combines progressive research, product, UX, and marketing to capture real-time thoughts, reactions, and behaviors of consumers at a scale. The solution features several products supporting recruitment, interviewing, and reporting of online research participants to provide businesses with contextual, real-life insights about their products and services.

Round of funding: B

Founder/ CEO: Michael Winnick

Funding: $11 M

Follow on: LinkedIn, Facebook, Twitter

2. Trunk Club

The next Chicago startup on our list has a mission to help every person look their best. To realize that goal, Trunk Club, a personalized clothing service, has affiliated with Nordstrom, an American chain of luxury department stores. 

The web and mobile apps (on iOS and Android) matches subscribers with a stylist who handpicks the best clothing and accessories and sends a preview selection to them. The customers then decide what to keep, and send back the rest, paying only for the purchased items. Trunk Club fosters a new approach to personalized shopping, offering a reasonable styling fee of $25 and making it easy for anyone to get out of a style rut.

Round of funding: A

Founder/ CEO: John Tucker, Kevin Price

Funding: $12.4 M

Follow on: LinkedIn, Facebook, Twitter

3. Yello.co

With over $40 million in funding, Yello.co is making its strides in in-person payments. The company brings marketing and payments together to the point of sales with a sleek portable tablet that supports a whole spectrum of payment methods (contact, contactless, QR, direct debit, and more).

The Android-based device comes with a set of turnkey bundled solutions for transaction processing and terminal management and enhances payment security thanks to the proprietary Switchable Optical Privacy Shield. With open Android OS, secure, proprietary yOS, and innovative Open-Browser mode, Yello is definitely staying on top of mobile development trends.

Round of funding: C

Founder/ CEO: Dan Bartfield, Jason Weingarten

Funding: $46.2 M

Follow on: LinkedIn, Twitter

4. Telnyx

David and Ian, the founders of Telnyx, have a shared goal of connecting people wherever they are. As they believe the standard Internet is insufficient to deliver the speed and consistency for real-time communications, they have built a platform that provides companies with carrier-grade, cloud-based telecommunications, and VoIP services. 

Telnyx offers a range of solutions spanning elastic SIP trunking, programmable SMS, call control portal, and APIs to enable managed services providers purchasing wholesale telecommunications services on demand. The business seems to have taken off, as in 2016, the company expanded its global footprint, opening the first remote office in Dublin.

Round of funding: Seed

Founder/ CEO: David Casem, Ian Reither

Funding: $1 M

Follow on: LinkedIn, Facebook, Twitter

5. The Mom Project

Every brilliant product starts with a story. The one behind the next Chicago startup is particularly relatable. When in 2015, Allison Robinson returned to work after giving birth to her son, she quickly experienced the harsh reality of being a working mom. Realizing she wasn’t the only woman struggling with reigniting her career after childbirth, she decided to build a platform that would unite all women facing similar challenges. 

The Mom Project is a digital talent marketplace and community for women who are trying to reconcile motherhood with career life. The website matches mothers with world-class employers to help them jump back into the working world after having a baby, and offers numerous auxiliary services, such as payroll, childcare, or catering, to support working moms further.

Round of funding: A

Founder/ CEO: Allison Robinson

Funding: $10.6 M

Follow on: LinkedIn, Facebook, Twitter

6. VillageMD

VillageMD supports physicians with an ecosystem of care coordination tools, on-the-ground resources, and big data analytics insights to streamline their work and turn their attention to what matters most – patient care. The company has undertaken to become the largest, highest performing primary care-led network in the nation. With the hefty funding of $80 million raised in 2018, it is well-positioned to succeed. 

VillageMD’s solutions feature a big data patient analysis platform, comprehensive EMR software, and a digital health operating system that extracts clinical and financial data sets from dozens of primary-care support systems and analyzes them in real-time to predict missing diagnoses, create patient engagement plans, and identify care gaps for healthcare professionals. 

Round of funding: Private

Founder/ CEO: Clive Fields, Paul Martino, Tim Barry

Funding: $116 M

Follow on: LinkedIn, Facebook, Twitter

7. ThreeKit

E-commerce is growing at an unprecedented rate, accounting for 15% of all retail sales in the U.S. One of the most powerful enablers of quality online shopping is 3D rendering, which provides an interactive, realistic 360-degree view of a product that is as close to the real-life experience as possible.

That’s the idea behind ThreeKit, a cloud-based visualization platform designed to help businesses present their products online in the most realistic way. The online solution comes with a set of user-friendly product configurators, sales aids, tutorials, and AR and VR tools to create high-quality, picture-perfect product visualization with ease and at scale.

Round of funding: Seed

Founder/ CEO: Ben Houston

Funding: $10 M

Follow on: LinkedIn, Facebook, Twitter

8. Paro

As with most things in the world, in freelancing, there are two sides to the story. On the one hand, it’s a highly-rewarding and flexible work model. On the other, with this flexibility comes the lack of stability. To help financial freelancers tackle this issue and provide them with a steady income, Paro’s founders set up a curated networking platform supporting freelance accountants, bookkeepers, and analysts.

Using technology, the platform matches businesses with vested freelance professionals to ensure on-demand, hourly support to clients. At the same time, it helps freelancers keep a regular flow of work. In the future, Paro foresees the use of predictive analytics to provide participating freelancers with a prognosis of their earnings ahead of the month.

Round of funding: Debt

Founder/ CEO: Dan Wywrot, Michael Burdick

Funding: $1.3 M

Follow on: LinkedIn, Facebook, Twitter

9. 1871

Next on our list is a non-profit entrepreneurial hub that unites graphic designers, engineers, and entrepreneurs and supports them in building own startups. Named after the memorable Great Chicago Fire, the startup accelerator represents everything that followed the dreadful event, “A remarkable moment when the most brilliant engineers, architects, and inventors came together to build a new city.”

The company founded in 2012 currently supports 500 early-stage, high-growth digital startups, and more than 1,500 members with office space, workshop and education opportunities, accelerator programs, and beyond. 

Round of funding: Seed

Founder/ CEO: Betsy Ziegler

Funding: $2.5 M

Follow on: LinkedIn, Facebook, Twitter

10. Boro

Boro, another top Chicago startup, is a leading consumer financing platform for college students and recent graduates, leveraging alternative data and machine learning to provide convenient and affordable financial solutions to young people who aren’t eligible for a credit in traditional banking institutions.

When the startup first launched in 2015 (under a different name), it started from providing automotive loans to students. Currently, the company has expanded its portfolio to include personal and cash loans as well.

Round of funding: A

Founder/ CEO: Hao Liu, Yifeng Ouyang

Funding: $8.6 M

Follow on: LinkedIn

11. LogicGate

LogicGate’s another brilliant example that made it to the list of best Chicago startups with a customizable, comprehensive platform that automates and simplifies risk-assessment and compliance processes. The platform features a user-friendly interface that can be easily personalized with a set of drag-and-drop forms and processes and a variety of built-in process apps.

Last year, the company closed $7.5 to grow their engineering, sales, product, and content teams and continue the development of their product.

Round of funding: A

Founder/ CEO: Dan Campbell, Jon Siegler, Matt Kunkel

Funding: $10 M

Follow on: LinkedIn, Facebook, Twitter

12. Journera

Here’s a sample of a travel agent’s daily routine: booking hotels, negotiating rates, searching for optimal routes, connecting flights, working out travel recommendations for customers. To make reconciling all these tasks a bit easier for travel professionals, Journera created a platform that designs unified travel experiences for their customers across airlines, hotels, transportation companies, and food providers.

The solution leverages a suite of APIs for easy integration with a host of hospitality companies, and data analytics algorithms to choose pertinent travel events and initiate their flow for a seamless customer travel experience. So far, Journera has noted a tremendous success, having passed the benchmark of 1 billion travel events, which represents over 110 million U.S. travelers.

Round of funding: A

Founder/ CEO: Jeffrey Katz

Funding: $9 M

Follow on: LinkedIn, Twitter

13. Fooda

With over 8,000 food businesses around, Chicago’s thrilling food scene offers much more than the iconic Deep Dish Pizza. Orazio Buzza, the founder of Fooda, determined to tap on that potential by bringing local restaurants into Chicago offices with a simple, intuitive mobile app. 

As a food technology platform, Fooda connects over 1,000 Chicago approved restaurants to people at work. With its clear-cut design and intuitive UX, the app is a perfect example of how to turn a simple idea into a valid business opportunity.

Round of funding: C

Founder/ CEO: Orazio Buzza

Funding: $34.2 M

Follow on: LinkedIn, Facebook, Twitter

14. Kin Insurance

Homeowner’s insurance varies from one company to another. Some packages are bloated with policies you are highly unlikely ever to need. Other offerings may seem comprehensive, while in reality, they exclude important coverage. 

Kin has seen an opportunity in data analysis to fix home insurance. The website streamlines the insurance application process and reduces it to a few simple steps, making use of online data points to create personalized, tailored insurance offers.

Round of funding: Venture

Founder/ CEO: Sean Harper, Sebastian Villarreal

Funding: $17.7 M

Follow on: LinkedIn, Facebook, Twitter

15. Clarity Insights

The last of our featured Chicago tech startups is a leader in data analytics, working with some of the nation’s bigger data-driven brands across multiple industries. 

Clarity Insights helps Fortune 1000 businesses take advantage of data and analytics to obtain customer intelligence, build a modern data architecture, increase consumer interaction with data-driven marketing strategies, and improve decision-making.

Round of funding: no data

Founder/ CEO: John Papadia, Jim Urhausen

Funding: no data

Follow on: LinkedIn, Facebook, Twitter


Did you enjoy our list of best Chicago startups? We hope it inspired you to build or expand your own web or mobile app that can make a real difference to your customers. 
If you need a hand with developing it, you know where to find us😉 Stay tuned for more startups from other U.S. cities.

Michał Rejman

Digital marketing specialist with a growth hacking mindset and 10+ years of experience. Michał’s goal is building high-quality technological content, with particular emphasis on React and RoR. Traveler, climber, remote work advocate.

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