50 Best Startups to Work For in Chicago in 2025

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
Paid sick days
Open door policy
Performance bonus
Company-sponsored outings
Commuter benefits
Apprenticeship programs
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

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 bring the world out to play 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 go-karts and the best ...
TOP PERKS + BENEFITS
Fitness stipend
Hybrid work model
Onsite office parking
Paid holidays
Onsite gym
Vision insurance

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
Mean gender pay gap below 10%
Summer hours
Pair programming
Flexible Spending Account (FSA)
Paid volunteer time
Free snacks and drinks
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
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
Remote work program
Free snacks and drinks
Mental health benefits
Home-office stipend for remote employees
Free daily meals
Disability insurance

Semasio

AdTech + Data Privacy
About us
Semasio is on a mission to harness the power of predictive intelligence now and in the future. We help data-driven marketers connect and build trust with consumers safely by creating access to a world where ads align with the content customers consume - the responsible way to drive growth in a privacy-first world. We operate predominantly out of ...
TOP PERKS + BENEFITS
Continuing education available during work hours
Team workouts
Family medical leave
Open door policy
Lunch and learns
Company-sponsored outings

Bloom Credit

Financial Services + Fintech
About us
Bloom Credit helps companies launch lending products, report consumers' payments, and create innovative credit experiences. We do this by providing our clients with the data they need from all three credit bureaus, the expertise they are looking for to launch seamlessly, and the proprietary analytics to supplement credit insights - all ...
TOP PERKS + BENEFITS
Open door policy
Paid volunteer time
Unlimited vacation policy
Family medical leave
Hybrid work model
Free snacks and drinks
What people are saying
"Bloom invests in the right technology for the job and bring in the right people to support their investment. Leadership is thoughtful and supports a great remote working environment."
Scott, IT Manager
About us
Braviant Holdings is a digital lending platform that combines breakthrough technology and cutting-edge machine learning to empower consumers with better credit solutions. This next-generation approach to lending is reducing credit barriers and creating a Path to Prime to help millions of underbanked consumers.
TOP PERKS + BENEFITS
Open door policy
401(K) matching
Employee-led culture committees
Online course subscriptions available
Life insurance
Paid industry certifications

Cadre

Financial Services + Fintech
About us
Cadre is a groundbreaking technology-driven commercial real estate investment platform that offers both institutional and individual investors the opportunity to access expertly curated real estate assets with lower minimums, low fees, and unprecedented potential for liquidity. Via its data-driven and transparent approach, Cadre opens ...
TOP PERKS + BENEFITS
Free snacks and drinks
Paid volunteer time
Mother's room
Family medical leave
Wellness programs
Disability insurance

DoStuff

Digital Media + Events
About us
DoStuff runs 22 local event guides (Do312, DoNYC, DoLA, etc) and a Ticket Membership that drives 60m event attendees a year. Our local teams make us a trusted part of the local scene, and our tech platform ensures we’re introducing people to the best stuff to do. We cover all events, not just those we’re paid to promote, because that leads to ...
TOP PERKS + BENEFITS
Pet friendly
Volunteer in local community
Hybrid work model
Vision insurance
Onsite office parking
Disability insurance

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
Mental health benefits
Relocation assistance
Fitness stipend
In-person all-hands meetings
Health insurance
Flexible Spending Account (FSA)
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, Recruiter

Shipium

Cloud + eCommerce
About us
Modern companies turn to Shipium when they want to increase revenue and decrease costs by adding new technology. Retailers, brands, 3PLs, and marketplaces use our enterprise shipping platform to power their operations across North America.
TOP PERKS + BENEFITS
Bereavement leave benefits
Diversity manifesto
Paid holidays
Generous PTO
Disability insurance
Mean gender pay gap below 10%

BenchPrep

Edtech + Enterprise Web
About us
BenchPrep helps the world's leading education, training, and assessment companies build and deliver best-in-class online learning programs. The platform is designed to personalize the learning experience for each user, adapting to their needs and progress. BenchPrep often offers mobile apps or responsive design, making it easy for learners to ...
TOP PERKS + BENEFITS
Day off for your birthday
Company-sponsored outings
Bereavement leave benefits
Performance bonus
Partners with nonprofits
Flexible time off

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
Highly diverse management team
Bereavement leave benefits
Remote work program
Fitness stipend
Mother's room
Onsite office parking
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

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
Home-office stipend for remote employees
Pet friendly
Floating holidays
Mandated unconscious bias training
Hiring practices that promote diversity
Team based strategic planning

PremiumIQ

Analytics + Artificial Intelligence
About us
PremiumIQ helps insurance companies increase premiums, reduce losses and engage customers with advanced data solutions. We assist data analytics teams in achieving faster results, fostering trust, and effectively managing costs. We’re data specialists focused singularly on helping insurance clients implement next generation applications, ...
TOP PERKS + BENEFITS
401(K)
Hybrid work model
Life insurance
In-person revenue kickoff
Performance bonus
Company-sponsored happy hours

Purple Carrot

eCommerce + Food
About us
Purple Carrot started with a seed of an idea in 2014 and is sprouting into the ultimate plant-based marketplace. We envision a world where plant-based eating is at the core of living well. Taste is at the center of what we do: good, vegan food for everyone. We value learning from customers, an ownership mindset, integrity, winning together, and ...
TOP PERKS + BENEFITS
Life insurance
Employee awards
Flexible Spending Account (FSA)
Quarterly engagement surveys
Hiring practices that promote diversity
Health insurance
jhelmy and company logo

JHelmy&Company

Analytics + Big Data
About us
We are committed to driving growth and change for our clients in a competitive business landscape. Our approach is innovative and collaborative, tailored to meet the unique needs of every client we partner with.

At JHelmy&Co, we thrive at building meaningful enhancements in our clients’ strategies and igniting transformative ...
TOP PERKS + BENEFITS
Documented equal pay policy
Disability insurance
Volunteer in local community
Flexible Spending Account (FSA)
Lunch and learns
Sabbatical

Ascent

Artificial Intelligence + Enterprise Web
About us
We’re leading the world of regulatory compliance forward by offering greater efficiencies, greater cost savings, and greater accuracy. Using market-leading RegulationAI, Ascent helps customers in financial services automate their compliance programs, significantly reducing their risk while saving time and money.
TOP PERKS + BENEFITS
Paid sick days
Pay transparency
Health insurance
Childcare benefits
Sabbatical
Home-office stipend for remote employees

Yello

Enterprise Web + HR Tech
About us
Yello is reinventing recruiting by replacing outdated practices with innovative solutions. Organizations from Fortune 500 companies use our technologies to modernize talent acquisition processes. Our culture emphasizes collaboration and supports rapid professional growth.
TOP PERKS + BENEFITS
Dental insurance
Childcare benefits
Volunteer in local community
Employee awards
Partners with nonprofits
Diversity employee resource groups

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
Dental insurance
Company sponsored family events
Diversity manifesto
Customized development tracks
Commuter benefits
Pet insurance

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
Recreational clubs
Commuter benefits
Onsite office parking
Flexible time off
In-person all-hands meetings

Quantum Rise

Artificial Intelligence + Automation
About us
At Quantum Rise, we're transforming how businesses use AI and automation to fuel growth and innovation. As an AI-native company, we combine human expertise with cutting-edge technology to solve real-world challenges. Our team is passionate about building products that are always on, continuously improving, and designed to help companies get ...
TOP PERKS + BENEFITS
Open office floor plan
Flexible time off
Wellness programs
401(K)
Flexible work schedule
401(K) matching
What people are saying
"I have never worked at an organization that prioritized its people the way Quantum Rise does. I see everyone here not just as experts, but also as people who are super willing to help out and learn about other departments, maintaining a culture of curiosity. Leadership trusts us, and that empowers us to think and act outside the box."
Melissa Smith, Head of Client Success

Stride Consulting

Consulting + Generative AI
About us
Stride is a strategic partner in driving technological transformation. With our team of seasoned engineers, designers, and product managers we go beyond the traditional boundaries of software development, and delivery, to achieve our clients goals and up-skill their teams.

As trailblazers in the utilization of generative AI, we’re ...
TOP PERKS + BENEFITS
OKR operational model
Company-sponsored happy hours
Diversity manifesto
Open office floor plan
Generous parental leave
401(K) matching

AdAction

AdTech + Digital Media
About us
At AdAction, we’re revolutionizing how brands connect with audiences through the power of mobile technology. As leaders in performance-driven marketing, we create innovative solutions that merge supply, loyalty, and rewards into seamless, mobile-first strategies. Our platform empowers brands and app developers to drive engagement, boost retention ...
TOP PERKS + BENEFITS
Lunch and learns
Home-office stipend for remote employees
Open door policy
Family medical leave
Health insurance
401(K) matching
What people are saying
"AdAction values cross-department knowledge sharing, fostering growth through collaboration and open communication. Learning from colleagues across teams has expanded my skills and industry understanding. The supportive, innovative environment makes it a place where both individual and collective success are celebrated!"
Tawni, Integrations Product Owner

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
401(K) matching
Generous parental leave
Health insurance
Promote from within
Continuing education available during work hours
Pet insurance

Sittercity

Kids + Family + Software
About us
Sittercity, a Bright Horizons company, is a technology platform working to reimagine the child care industry. Finding, hiring and managing high-quality, trustworthy and enriching child care has never been simple, for parents or caregivers. We want to change that. At Sittercity, you can imagine and create solutions that will revolutionize a multi- ...
TOP PERKS + BENEFITS
Life insurance
Mandated unconscious bias training
Hiring practices that promote diversity
Childcare benefits
Dedicated diversity and inclusion staff
Mental health benefits
What people are saying
"Sittercity has exposed me to different facets of the company and given me room to grow my career. The opportunity for career growth and the exceptional colleagues I interact with everyday make me happy to work at Sittercity."
Erika, Customer Success Manager
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
Dental insurance
Volunteer in local community
Charitable contribution matching
Pair programming
Vision insurance
Company-sponsored happy hours
About us
Upfront delivers dynamic, digital care navigation to improve patient experience, increase necessary visits, reduce no-shows, and improve population health performance. Its flexible omnichannel communication capabilities, combined with personalized patient content and calls-to-action, eliminate common barriers to patient engagement and enable ...
TOP PERKS + BENEFITS
Mandated unconscious bias training
Dedicated diversity and inclusion staff
Company-sponsored happy hours
Flexible Spending Account (FSA)
Hybrid work model
Generous PTO

Brad's Deals

eCommerce + Information Technology
About us
Brad’s Deals brings together the best deals on the internet, all in one place. We’ve grown from a one-person operation in 2001 to a 65-person, employee-owned company that helped shoppers save more than $100 million in 2014.

In addition to company growth, we’re committed to helping employees grow professionally. We fund ongoing ...
TOP PERKS + BENEFITS
Dental insurance
Fitness stipend
Wellness programs
Company equity
Health insurance
Paid sick days
About us
Deinde builds cutting-edge financial technology supercharged by sophisticated analytics framework. Today we offer flexible credit products to consumers in need of small-dollar, personal loans.
TOP PERKS + BENEFITS
Floating holidays
Wellness programs
Paid holidays
Mentorship program
Flexible time off
Bereavement leave benefits

Metafora

Information Technology + Logistics
About us
Metafora (formerly CarrierDirect) is a business consulting and software development company that exclusively serves the transportation, logistics and supply chain space. We partner with carriers, shippers, and freight tech vendors to help them optimize their business and build software to fuel their growth. We live at the intersection of strategy ...
TOP PERKS + BENEFITS
Team based strategic planning
Highly diverse management team
Job training & conferences
Family medical leave
Mandated unconscious bias training
Paid volunteer time
Engtal

Engtal

Agency + Professional Services
About us
The search is on for the best engineering and technology talent in the market. We deliver talent solutions that connect our technology and engineering communities.

From start-ups to tech and engineering giants, we support the game changers, the inventors, and the market disruptors to ensure they have the right talent in place, ...
TOP PERKS + BENEFITS
Disability insurance
Paid sick days
Free snacks and drinks
Lunch and learns
Mental health benefits
Diversity employee resource groups

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
Dental insurance
Paid sick days
401(K) matching
OKR operational model
Flexible Spending Account (FSA)
Remote work program
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

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
Some meals provided
Quarterly engagement surveys
Promote from within
Remote work program
Health insurance
Highly diverse management team
Made in Tandem brand mark

Made in Tandem

Agency + Consulting
About us
Made in Tandem is a trusted strategy, design, and technology partner. We deliver custom software that inspires people and drives business forward. Our unique process brings every voice to the table. We engage with customers, researchers, engineers, and designers in order to approach every problem with a broad set of perspectives.
TOP PERKS + BENEFITS
Hiring practices that promote diversity
Generous parental leave
Disability insurance
Family medical leave
Life insurance
Paid sick days

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
Generous parental leave
Open door policy
Open office floor plan
Performance bonus
Team based strategic planning
Paid sick days
Atomic Object Logo

Atomic Object

Agency + App development
About us
Our co-located, U.S.-based team works with executives to improve their bottom line by delivering new products, enhancing existing products, modernizing legacy products, and integrating AI into their software systems. Atomic is an employee-owned company with offices in Grand Rapids, Ann Arbor, Chicago, and Raleigh-Durham.
TOP PERKS + BENEFITS
Mentorship program
Wellness programs
Tuition reimbursement
Mental health benefits
Employee awards
Employee stock purchase plan

Practifi

Cloud + Financial Services
About us
Practifi is the leading CRM purpose-built for wealth management. By surfacing key insights, automating workflows and enabling personalized client experiences that fortify relationships, Practifi transforms how financial professionals connect with and grow their client base. Bringing together opportunities to strengthen client loyalty, enhance team ...
TOP PERKS + BENEFITS
401(K) matching
Employee awards
Wellness days
Free snacks and drinks
Volunteer in local community
Company-sponsored happy hours

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
Health insurance
401(K) matching
Diversity Program
Life insurance
Online course subscriptions available
Onsite gym
Albi Blue Logo

Albi

Software
About us
At Albi, we’re a mission-driven organization, passionate about empowering the unsung heroes of the restoration industry. Restorers work tirelessly to rebuild homes, businesses, and communities after disasters — they deserve tools that help them unlock their full potential. Our core values drive everything we do: we go the extra mile, embrace ...
TOP PERKS + BENEFITS
Performance bonus
Health insurance
Personal development training
President's club
Company-sponsored outings
Paid holidays

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
Company equity
Dental insurance
Performance bonus
Hiring practices that promote diversity
Customized development tracks
Flexible work schedule

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
Mean gender pay gap below 10%
Onsite gym
In-person all-hands meetings
Lunch and learns
Remote work program
Free snacks and drinks

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
Generous PTO
Paid sick days
Open door policy
Open office floor plan
Remote work program
Company-sponsored outings

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
Fitness stipend
Vision insurance
Job training & conferences
401(K)
Pet friendly
Mental health benefits

PartySlate

Asset Management + Discovery + Consumer Web
About us
PartySlate is a fast-paced Chicago startup disrupting the $156 billion events industry in the United States. There are 13 million parties per year, produced by over 460,000 venues and vendors. PartySlate connects people planning all types of events — from weddings and corporate events to galas and milestone birthdays — with the venues and vendors ...
TOP PERKS + BENEFITS
Mother's room
Summer hours
Hiring practices that promote diversity
Some meals provided
Mean gender pay gap below 10%
Unlimited vacation policy
What people are saying
"I truly love working at PartySlate and being part of the product team! From the moment I started working here, I am constantly getting opportunities to grow and challenge myself with fun new projects. The team is so supportive and eager to help!"
Katy, Software Engineer

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
Life insurance
401(K) matching
Paid holidays
Generous PTO
Vision insurance

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
Paid holidays
Team based strategic planning
Commuter benefits
OKR operational model
Company-sponsored outings
Paid volunteer time

LaunchPad Lab

App development + Consulting
About us
LaunchPad Lab is a technology consulting firm that brings an advanced product skillset to design, develop, and deliver software applications that get results. Our experienced teams empower businesses to make technology a competitive advantage. We’ve helped hundreds of businesses in financial services, healthcare, legal, manufacturing, non-profit, ...
TOP PERKS + BENEFITS
Health insurance
Company-sponsored happy hours
Paid holidays
Unlimited vacation policy
401(K) matching
Open door policy
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
Company-sponsored happy hours
Disability insurance
Health insurance
Company-sponsored outings
Tuition reimbursement
Commuter benefits

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