50 Best Startups to Work For in Chicago, IL 2023

Radio Flyer

Design + eCommerce
About us
Radio Flyer is known for our iconic little red wagon, and we are always dreaming up FUNomenal new ways to deliver joy to families by introducing new products every year. Radio Flyer is a recognized leader in the toy industry, with our corporate headquarters located in Chicago. From wagons and tricycles to battery powered eBikes, Go-Karts and Tesla ...
TOP PERKS + BENEFITS
Volunteer in local community
Lunch and learns
401(K) matching
Hiring practices that promote diversity
OKR operational model
Commuter benefits

Pangea Money Transfer

Fintech + Mobile
About us
Pangea is a digital money transfer platform that makes sending money abroad simple, reliable, and cost-effective. Founded in 2012 and based in Chicago, we’ve helped millions of people send money securely and efficiently, empowering financial freedom across borders.

We serve a global customer base with a mobile-first platform that ...
TOP PERKS + BENEFITS
Vision insurance
Paid industry certifications
Employee stock purchase plan
Summer hours
Commuter benefits
Life insurance
What people are saying
"Pangea offers the opportunity to be involved in the full design and development process. I am able to fully understand the product and architecture, while putting the best solution forward. I have added many skills that have advanced me in my career."
Keerthi Maryala, Engineering Manager Read all reviews
Grand Studio logo

Grand Studio

Consulting + Financial Services
About us
Grand Studio is a strategic design firm—home to talented thinkers and makers who collaborate around digital and operational design. Together, we take on complex challenges to build clearer paths and tools for success.
We solve problems to meet users and businesses where they’re at. For some partners, our approach results in digital products ...
TOP PERKS + BENEFITS
401(K) matching
Return-to-work program post parental leave
Family medical leave
Transgender health care benefits
Mandated unconscious bias training
Open door policy
Network Perception Logo

Network Perception

Cybersecurity + Security
About us
Network Perception protects mission-critical assets by empowering cybersecurity and compliance teams to achieve high levels of cyber resiliency through verification, visibility, and velocity. Built by a government-funded research team of cybersecurity and industry experts in network security and critical infrastructure protection, the NP-View ...
TOP PERKS + BENEFITS
Open door policy
Hiring practices that promote diversity
Job training & conferences
Generous PTO
Paid volunteer time
Online course subscriptions available

Supernova Technology

Cloud + Fintech
About us
Supernova is the technology leader in securities-based lending ("SBL") solutions that connect and empower the entire financial ecosystem. We offer the world’s first and only cloud-based, fully-customizable, end-to-end software solution to automate securities-based lending from origination through the life of the loan.
TOP PERKS + BENEFITS
Free daily meals
Onsite gym
Company sponsored family events
Team based strategic planning
Commuter benefits
Life insurance
What people are saying
"I really enjoy working at Supernova and love our team! We are a small team, but we are so effective and productive in many ways. It feels super good to ‘grow up’ with the company together – and to see how different it is day by day. "
Daisy Yang, Manager, Data Analyst Read all reviews

Kalderos

Analytics + Big Data
About us
Kalderos is a data infrastructure and analytics company that’s solving challenges around drug discounts in the U.S. healthcare system. Through platform technology and big data, our team is delivering smart solutions that enable healthcare stakeholders to collaborate with greater transparency and trust. We’re passionate about our mission to take on ...
TOP PERKS + BENEFITS
Paid holidays
Bereavement leave benefits
Free snacks and drinks
Unlimited vacation policy
Charitable contribution matching
Health insurance
What people are saying
"The people at Kalderos thrive in an environment focused on collaboration, which set us up for success. With our diverse backgrounds and talents, we’re able to leverage our experiences and strengths to work together to succeed in a common mission."
Steve, Director, Industry Relations Read all reviews

Pareto Intelligence

Big Data + Healthtech
About us
Pareto Intelligence is a leading healthcare solutions company modernizing the way health plans and providers succeed in value-based care. We deliver analytics, technology and advisory solutions, supported by predictive models and advanced data science, that demystify complex healthcare data and deliver actionable predictions that improve outcomes.
TOP PERKS + BENEFITS
Health insurance
Paid holidays
Life insurance
Generous PTO
Dental insurance
Vision insurance

Allwyn North America

Consumer Web + eCommerce
About us
Allwyn North America is a full-service lottery operator, supplier, and business partner to North American lotteries. We make play better for all with innovative lottery technology and services, engaging content, and tried-and-tested playbooks that responsibly grow lotteries’ player base, revenue, and returns to good causes over time. As operating ...
TOP PERKS + BENEFITS
Online course subscriptions available
401(K)
Continuing education stipend
Some meals provided
Continuing education available during work hours
Commuter benefits
What people are saying
"Working for Allwyn has been enjoyable in many ways! It's exciting & rewarding to be apart of building something special from the ground up. My co-workers are all helpful and very knowledgeable from many different backgrounds."
Michael , Director of Retail Sales Read all reviews
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GeoWealth

Fintech + Software
About us
GeoWealth provides wealth management technology; combining a comprehensive and fully-integrated platform with best-in-class portfolio solutions. Our customizable open-architecture platform and our proven spectrum of investment strategies address all the essential needs of RIAs by helping them grow faster and serve their clients more efficiently.
TOP PERKS + BENEFITS
Performance bonus
Free snacks and drinks
Health insurance
Lunch and learns
Continuing education stipend
Paid industry certifications

Prosodica

Analytics + Artificial Intelligence
About us
Prosodica transforms the way organizations understand and improve human connection. Our AI-powered conversation analytics platform captures every nuance of human dialogue—tone, pacing, empathy, and engagement—and translates it into measurable data that leaders can act on. By quantifying what was once intangible, Prosodica helps enterprises build ...
TOP PERKS + BENEFITS
Relocation assistance
Employee-led culture committees
Onsite office parking
Apprenticeship programs
Commuter benefits
Documented equal pay policy
What people are saying
"Prosodica stands out for balancing cutting-edge technology with genuine human connection. We build meaningful solutions together, and the company’s focus on growth, support, and open communication has helped me become more confident and capable in my role."
Megan, Manager, Customer Success Read all reviews

Avaneer Health

Big Data + Healthtech
About us
Avaneer Health's mission is to unlock the potential of healthcare to do more for people. Built on secure technology to ensure privacy and reduce the costs of data exchange, we serve providers of services across the healthcare industry. Avaneer Health is a member-based, secure and open network supporting utilities developed for and by the ...
TOP PERKS + BENEFITS
Meditation space
Company-sponsored happy hours
401(K) matching
OKR operational model
Team based strategic planning
Company equity

ReviewTrackers

Business Intelligence + Enterprise Web
About us
ReviewTrackers is the award-winning customer feedback software that helps businesses measure and transform the customer experience. The platform collects review data from 100+ review sites to surface customer insights that enable brands to listen, comprehend and make data-driven decisions about what their customers truly need or want.
TOP PERKS + BENEFITS
Flexible Spending Account (FSA)
Promote from within
Vision insurance
Mandated unconscious bias training
Employee stock purchase plan
Remote work program
About us
High Definition Vehicle Insurance (HDVI): Technology meets Insurance. HDVI brings telematics, software and data together with commercial trucking insurance, taking transportation insurance and fleet risk management to the next level. Our platform arms fleets with an end-to-end solution that empowers them to save money, mitigate risk, and increase ...
TOP PERKS + BENEFITS
Unlimited vacation policy
Promote from within
Commuter benefits
Vision insurance
401(K) matching
Health insurance

OneSix

Analytics + Artificial Intelligence
About us
OneSix is a leading data and artificial intelligence consultancy that helps businesses build the strategy, technology, and teams they need to innovate and grow. We excel at solving complex problems through integrated teams of strategists, data engineers, data scientists, and AI and machine learning experts.
TOP PERKS + BENEFITS
OKR operational model
Open office floor plan
Online course subscriptions available
Mental health benefits
Relocation assistance
Team based strategic planning

Cervantes Group

Information Technology
About us
At The Cervantes Group, we are laser focused on achieving our customers business strategic goals and global innovations on a collaborative basis. Our team specializes in delivering rapid Agile™ App Dev, Project Management, Business Analysis and Management Consulting leveraging an excellent multi-lingual, multi-cultural and multi-talented team ...
TOP PERKS + BENEFITS
Wellness programs
401(K)
Friends outside of work
Team workouts
Online course subscriptions available
Flexible work schedule

MVMNT

Fintech + Logistics
About us
Transform a Trillion Dollar Industry

When you work at MVMNT, you’re tackling real life problems—and shaking up a trillion dollar industry in the process. MVMNT is a Chicago-based freight tech startup founded in 2020. Our mission is to enable small & medium-sized brokerages with enterprise-level technology and embedded financial ...
TOP PERKS + BENEFITS
Paid sick days
Company-sponsored happy hours
Health insurance
Mentorship program
Free snacks and drinks
Mental health benefits

CityBase

Information Technology + Other
About us
Our technology helps people find, apply, and pay for public services — and helps staff manage those interactions. The CityBase platform equally serves people who want to complete a task from their phones, those who are underbanked and must pay a bill in cash, and the public servants who keep government and utilities running smoothly.
TOP PERKS + BENEFITS
401(K) matching
Paid sick days
Company-sponsored happy hours
Commuter benefits
Remote work program
Generous PTO

Focused

Artificial Intelligence + Cloud
About us
Focused is a software services company that builds agentic AI and custom software. Our expert engineers and designers build custom agents that integrate seamlessly with the systems you already run. What sets Focused apart is our hands-on, collaborative approach. We don’t just build and deliver software, we partner with your teams to ensure that we ...
TOP PERKS + BENEFITS
401(K)
Family medical leave
Paid industry certifications
Dental insurance
Highly diverse management team
Pair programming

Black Spectacles

eCommerce + Edtech
About us
Black Spectacles helps educate and inspire architects around the world to thrive in their career. We are an online learning platform, offering ARE® prep, software curriculum and career insight from the best and brightest in the biz. We are the industry leader as the first NCARB-approved test prep provider for all six divisions of the ARE 5.0.
TOP PERKS + BENEFITS
Some meals provided
Volunteer in local community
Remote work program
Health insurance
Commuter benefits
OKR operational model

Obie

Insurance + PropTech
About us
Obie is the leading investment property insurance platform, providing landlords, real estate investors, and partners with instant quotes, tailored coverage, and an entirely digital experience. Backed by proprietary technology, Obie simplifies insurance so deals can close faster and investors can move forward with confidence. Whether they’re ...
TOP PERKS + BENEFITS
Wellness programs
Lunch and learns
Remote work program
Return-to-work program post parental leave
Some meals provided
Onsite gym

CPI OpenFox

Legal Tech + Software
About us
Computer Projects of Illinois, Inc. (CPI), is a privately held corporation that delivers market-leading software solutions to the law enforcement industry. CPI develops & maintains many different best-in-class, mission-critical criminal justice solutions to law enforcement & public safety agencies around the world with their OpenFox® ...
TOP PERKS + BENEFITS
Documented equal pay policy
Paid holidays
Vision insurance
Mean gender pay gap below 10%
Disability insurance
Meditation space
What people are saying
"What I like working about working at CPI is the people. I laugh at least once every day (even on the "bad" days)."
Milette, Sr. Software Engineer Read all reviews

cohesion

PropTech + Real Estate
About us
Cohesion is a smart building technology company offering a suite of software products, AI solutions, and advisory services that integrates people, systems, and spaces for real estate, providing seamless solutions for modernized security access control, smart maintenance, enhanced people experiences, and energy management.
TOP PERKS + BENEFITS
Commuter benefits
Relocation assistance
Onsite gym
Life insurance
Dental insurance
Free snacks and drinks

Purchasing Platform

eCommerce + PropTech
About us
Purchasing Platform is a unique B2B marketplace tailored for all sectors of property management. We leverage cutting-edge technology to empower property portfolios, enabling them to manage purchasing activities efficiently across all properties while driving real cost savings from trusted suppliers. Our platform services portfolios across the ...
TOP PERKS + BENEFITS
Home-office stipend for remote employees
Pet friendly
Promote from within
Diversity employee resource groups
Open office floor plan
Mandated unconscious bias training
What people are saying
"Purchasing Platform has allowed me to grow along with the business. Our leadership team is transparent, supportive, and willing to explore ideas from anyone within the organization. I'm constantly looking forward to what comes next. "
Elliot , Strategic Projects Coordinations Manager Read all reviews
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Analytics8

Analytics + Big Data
About us
We help companies translate their data into meaningful and actionable information so they can stay ahead in a rapidly changing world.  

We know data and analytics can be complicated and overwhelming. But data and analytics is all we do, and we are here to guide you through the complexities - so you can make sense of your data and ...
TOP PERKS + BENEFITS
OKR operational model
Generous parental leave
Flexible Spending Account (FSA)
In-person all-hands meetings
Employee awards
Free daily meals
What people are saying
"My skills and opinions are valued at Analytics8. I love that I am continually learning and growing my skill set."
Jen, Marketing Read all reviews

CardX

Fintech + Payments
About us
CardX provides solutions for businesses to accept credit cards at 0% cost, making payments more fair for everyone. We offer technology-enabled compliance with the card brand rules, allowing businesses to keep their payments acceptance simple while providing their customers the option to pay by card.
TOP PERKS + BENEFITS
401(K) matching
Some meals provided
Open office floor plan
Flexible work schedule
Generous parental leave
Online course subscriptions available

UPshow

Digital Media + Marketing Tech
About us
UPshow, the leading in-venue entertainment and marketing platform, is the first and only provider of white-labeled, digital interactive networks for retail and hospitality brands to engage customers and employees directly from their mobile devices.

UPshow’s technology makes it simple for large brands to build and launch engaging and ...
TOP PERKS + BENEFITS
Summer hours
Generous parental leave
Paid holidays
Commuter benefits
Performance bonus
Remote work program

oak9

Cloud + Cybersecurity
About us
At oak9, we are passionate about removing the friction between development and security so that businesses can achieve development velocity and agility without compromising on security. We are a SaaS company with a cloud native security automation platform that analyzes infrastructure-as-code and seamlessly integrates into existing development ...
TOP PERKS + BENEFITS
Return-to-work program post parental leave
Free snacks and drinks
Health insurance
Unlimited vacation policy
Paid holidays
Continuing education available during work hours

Topstep

Fintech
About us
Trading is more than an activity, more than a passion, more than a calling. It’s a lifestyle, a set of rules, and a mentality towards every aspect of your day. We’ve seen what happens to people who don’t buy into the rules or the mentality—they fail, time and time again. At Topstep, we are passionately committed to helping our customers find true ...
TOP PERKS + BENEFITS
Beer on Tap
Recreational clubs
Job training & conferences
Pet insurance
Volunteer in local community
Paid industry certifications

Tandym

Fintech
About us
Tandym helps merchants drive deeper loyalty with their customers. With Tandym’s modern, API-driven platform, merchants can configure and deploy their own branded credit and loyalty program with just a few clicks. This branded payment product helps merchants convert credit card transaction processing costs into future customer revenues through ...
TOP PERKS + BENEFITS
Home-office stipend for remote employees
Hiring practices that promote diversity
Unlimited vacation policy
Dental insurance
Lunch and learns
Group brainstorming sessions

Adage Technologies

eCommerce + Professional Services
About us
Founded in 2001, Adage Tech is a web design and development firm combines strategic thinking with a passion for technology to advance our client's purpose. We bring together a diverse team of creative and technical professionals who partner with our clients to create their digital strategy and build applications to connect with their ...
TOP PERKS + BENEFITS
Onsite gym
Lunch and learns
Pair programming
Paid industry certifications
Meditation space
Flexible work schedule
What people are saying
"At Adage I'm surrounded by people who are not only smart, but dedicated and passionate about what they do. Everyone here is actively trying to do their best work and help one another to do the same."
Victoria Sullivan, Director of People and Culture Read all reviews

Aclaimant

Analytics + Financial Services
About us
We are an innovative insurance tech startup redefining the way companies and employees work together to manage risk. When incidents happen in the workplace, the process is often confusing, scary, and frustrating – for both employers and employees. We build software that changes all that. Join our team to help revolutionize commercial insurance!
TOP PERKS + BENEFITS
Pair programming
Wellness programs
Onsite gym
Company equity
Pet friendly
Paid holidays

Neighborhoods.com

Real Estate + Software
About us
Neighborhoods.com is the first online real estate resource to put the neighborhood at the center of the home search. The platform invites visitors to imagine their life in a new area by providing a local’s perspective, including detailed descriptions and resident reviews of schools, amenities, and the surrounding community.
TOP PERKS + BENEFITS
Documented equal pay policy
Mandated unconscious bias training
Health insurance
Paid holidays
Job training & conferences
Commuter benefits

Redstone

Artificial Intelligence + Fintech
About us
Redstone is one of the fastest growing fintech startups in the country focused on streamlining creation of esoteric alternative asset classes. The fintech disruptor dismantled the MBS ecosystem, streamlining it with a digital platform that employs AI and machine learning tools to eliminates unnecessary steps and redundant approval processes.
TOP PERKS + BENEFITS
Generous PTO
Highly diverse management team
Open office floor plan
Paid sick days
Vision insurance
OKR operational model

ClearCut Analytics

Big Data + eCommerce
About us
ClearCut is a leading provider of retail analytics for CPG brands. With over $50B in eCommerce and Amazon sales data analyzed, our intelligence delivers actionable insights into today's complex retail marketplace to power successful product innovation and optimize digital shelf performance. Beyond analytics, we offer expert-led services for ...
TOP PERKS + BENEFITS
Mentorship program
Generous parental leave
Open door policy
Paid holidays
Company-sponsored outings
Return-to-work program post parental leave

MARKT-PILOT

Analytics + Artificial Intelligence
About us
Feel the pulse of the market for the first time with MARKT-PILOT!

Our mission is to provide complete market intelligence for your entire spare parts offering.

With the help of our innovative software, PRICE-RADAR, we revolutionize spare parts pricing and create sustainable growth for OEMs' parts revenue. ...
TOP PERKS + BENEFITS
Eat lunch together
Cross functional training encouraged
Family medical leave
401(K)
Promote from within
Diversity Program

Accelerated Digital Media

Agency + Digital Media
About us
Accelerated Digital Media is a bootstrapped company that has recruited some of the top talent in digital marketing. We're on a mission to create one of the country's top digital marketing firms.

ADM is a team of performance marketers specializing in paid media management for high-growth Digital Health and e-commerce ...
TOP PERKS + BENEFITS
Open office floor plan
Vision insurance
Life insurance
Promote from within
Open door policy
Home-office stipend for remote employees

Cured

Digital Media + Healthtech
About us
Cured’s platform solutions enable leading healthcare organizations to better manage patient and key partner relationships in their networks, perform outreach directly to patients via the channels of their preference, and improve patient access experience and efficacy.
TOP PERKS + BENEFITS
Casual Dress
Unlimited vacation policy
Performance bonus
Volunteer in local community
Daily sync
Pet friendly

Live Bash

News + Entertainment + NFT
About us
Live Bash is an entertainment technology startup that is building high-tech performer centric stages for Livestream performances. Performers of all types (musicians, comedians, interviewers, dancers, etc) can easily reserve a fully staffed turnkey venue where digital collectibles of their Livestream performance can be purchased by fans.
...
TOP PERKS + BENEFITS
Friends outside of work
Unlimited vacation policy
Group brainstorming sessions
Open door policy
Diversity manifesto
Casual Dress

2nd Watch

Analytics + Big Data
About us
Aptitive is a Chicago-based IT consulting firm with solutions focusing on the management, design, and development of data-centric projects. Our high-aptitude consultants bring innovative technology solutions to your business problems.
TOP PERKS + BENEFITS
Intracompany committees
401(K)
Some meals provided
Generous PTO
Charitable contribution matching
Free snacks and drinks

ShoppingGives

eCommerce + Fintech
About us
ShoppingGives is connecting cause with commerce. From DTC brands to Enterprise retailers, thousands of businesses are using ShoppingGives to launch, scale, and optimize their charitable giving strategies. Our Social Impact Stack is at the center of where purpose meets profit, and exists to empower brands to motivate giving, build loyalty, and ...
TOP PERKS + BENEFITS
Health insurance
Vision insurance
Online course subscriptions available
Mentorship program
Open office floor plan
Mental health benefits

Milyli

Enterprise Web + Information Technology
About us
Milyli builds secure, intuitive software that makes managing sensitive information tasks easier. Milyli has worked with Relativity and other eDiscovery technologies since 2008, building custom solutions and developing innovative applications like our flagship redaction tool, Blackout. The world’s top law firms, services providers, and government ...
TOP PERKS + BENEFITS
Casual Dress
Family medical leave
Daily sync
Diversity manifesto
Team based strategic planning
Diversity employee resource groups

Equilibria

Cannabis + eCommerce
About us
Equilibria is a high-growth, omni-channel premium CBD platform for women. We are dedicated to restoring balance to our community — physically and mentally — through our high quality CBD products and personalized dosage & delivery support.
TOP PERKS + BENEFITS
Company-sponsored happy hours
Remote work program
Generous PTO
Mental health benefits
Casual Dress
Family medical leave

Bento for Business

Fintech + Software
About us
At Bento, our mission is to give businesses the freedom to drive their vision, empower their employees and deliver business growth. We do that with our awesome financial operating platform that makes it easy for SMBs to manage daily expenses, virtual payments and cashless workflows. We are serving thousands of (very) happy customers and growing!
TOP PERKS + BENEFITS
Free snacks and drinks
Unlimited vacation policy
Company equity
OKR operational model
Disability insurance
Vision insurance

Heggerty

eCommerce + Edtech
About us
Heggerty is a literacy education company providing the #1 phonemic awareness curriculum for preschool and elementary classrooms. Founded nearly 20 years ago by Dr. Michael Heggerty, a reading instruction pioneer, we provide digital and print curriculum, classroom resources, and professional development to help educators empower the next generation ...
TOP PERKS + BENEFITS
Open office floor plan
Health insurance
Casual Dress
Generous PTO
Dental insurance
Team based strategic planning

WayFinder Logistics

Logistics + Transportation
About us
WayFinder Logistics is a third-party logistics provider located in the heart of Chicago. WayFinder combines experienced professionals, a culture predicated on integrity, accountability, and an undying thirst to provide solutions for customers and carriers alike. At WayFinder, we will outwork and outperform the competition to deliver a best-in- ...
TOP PERKS + BENEFITS
Free snacks and drinks
Tuition reimbursement
Company-sponsored outings
401(K)
Generous PTO
Flexible work schedule
About us
Yakkety Yak helps business find the right words to connect with their target audience. Our content marketing services encompass everything from website copy, custom blogs and newsletters, content audits, press releases, case studies, social media marketing and custom publishing. We want to figure out how to say what you want to say – so let’s YAK.
TOP PERKS + BENEFITS
Pet insurance
Open office floor plan
Health insurance
Job training & conferences
Lunch and learns
Unlimited vacation policy

Anthill

HR Tech
About us
Connect your frontline workforce to company resources with Anthill - the only two-way text-based communication tool designed for frontline workers to provide simple-to-use, secure employee communication in over 110 languages. Developed by workforce experts, Dr. Muriel Clauson and Dr. Young-Jae Kim, the award-winning 24-7 channel provides all ...
TOP PERKS + BENEFITS
Wellness programs
Family medical leave
Cross functional training encouraged
Documented equal pay policy
401(K) matching
Open door policy

Nextpoint

Big Data + Cloud
About us
Nextpoint is the industry leader in delivering cloud-based services for eLaw. Our market leading software and services help legal related organizations conquer their eDiscovery, Litigation and Admin needs. We do this by providing a powerful SaaS platform with world-class support and engagement teams that help hundreds of law firms across the ...
TOP PERKS + BENEFITS
Performance bonus
Some meals provided
OKR operational model
Remote work program
Summer hours
Return-to-work program post parental leave
What people are saying
"It mattered to me to join a company whose culture I could speak about with honesty and pride. Nextpoint continues to strengthen its commitment to inclusion, creating a workplace that feels like a connected, supportive community for everyone."
Grace, Recruitr Read all reviews

Perfect Search Media

AdTech + Design
About us
Perfect Search Media is a Chicago-based digital marketing agency.

We’re experts in Paid Search and Social Media Advertising, SEO, Remarketing, Display, UX, Design, and Content. We’re a results-driven, remote company with teammates from coast to coast.
TOP PERKS + BENEFITS
Performance bonus
OKR operational model
Daily sync
401(K)
Life insurance
Mental health benefits

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