Best Startups to Work For in Chicago in 2026

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
Bereavement leave benefits
Mandated unconscious bias training
Relocation assistance
Employee-led culture committees
Disability insurance
Hiring practices that promote diversity
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
401(K)
Fitness stipend
Hybrid work model
Paid volunteer time
Continuing education available during work hours
Company-wide vacation

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
Customized development tracks
Fitness stipend
Job training & conferences
Company-sponsored happy hours
Free daily meals
Sabbatical
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
Transgender health care benefits
Remote work program
Hiring practices that promote diversity
Team based strategic planning
Disability insurance
Life 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
Fertility benefits
OKR operational model
Transgender health care benefits
Lunch and learns
Generous parental leave
Dental insurance

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
Flexible Spending Account (FSA)
Unlimited vacation policy
Open door policy
Employee awards
Free snacks and drinks
Company-sponsored happy hours
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

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
Company-wide vacation
Diversity manifesto
Diversity recruitment program
Disability insurance
Dedicated diversity and inclusion staff
Bereavement leave benefits

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
Flexible work schedule
Free snacks and drinks
Hybrid work model
Some meals provided
Company-sponsored outings
401(K) matching

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
Personal development training
Charitable contribution matching
Flexible Spending Account (FSA)
Paid holidays
Partners with nonprofits
Disability insurance
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

Flatfile

Artificial Intelligence + Database
About us
Flatfile, the pioneer of AI-assisted data exchange, provides companies and their software development teams with the easiest, fastest, and safest way to build the ideal data file import experience for their users. Hundreds of companies such as AstraZeneca, Square or Sage rely on Flatfile’s extensible, API-first platform to create enterprise-scale ...
TOP PERKS + BENEFITS
Hiring practices that promote diversity
Pair programming
Mandated unconscious bias training
Unlimited vacation policy
Wellness programs
Disability insurance
What people are saying
"Flatfile is the company you want to grow with. It’s open to people from versatile backgrounds and with differing interests. Finding new opportunities for professional growth and pursuing your goals with Flatfile is easy."
Marina, Enterprise Sales Development

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
Mental health benefits
Volunteer in local community
Commuter benefits
Company-wide vacation
Some meals provided
Paid holidays

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
Return-to-work program post parental leave
Mandated unconscious bias training
Vision insurance
Generous parental leave
Commuter benefits
Open office floor plan

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
Hybrid work model
Onsite office parking
401(K)
Disability insurance
Hardship benefits
Floating holidays

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
Life insurance
Hybrid work model
Paid industry certifications
Mentorship program
OKR operational model
Company-sponsored outings
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

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
Performance bonus
Company equity
Vision insurance
Company-sponsored happy hours
Virtual coaching services
OKR operational model

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
In-person all-hands meetings
Flexible Spending Account (FSA)
Performance bonus
Job training & conferences
Team based strategic planning
Employee awards
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
Paid holidays
Vision insurance
Meditation space
Restricted work hours
Pet friendly
Home-office stipend for remote employees

Moov

Fintech + Payments
About us
Moov is a payments infrastructure platform making it easy to accept, store, send, and spend money all from a single, elegantly-designed API. Instead of stitching together multiple vendors, software companies simply add Moov to their products to get the latest in payment technology, user onboarding, licensing, compliance, and more.
TOP PERKS + BENEFITS
Mean gender pay gap below 10%
Paid industry certifications
Company-sponsored happy hours
Mentorship program
Company-wide vacation
Flexible Spending Account (FSA)
What people are saying
"Each day at Moov brings a new challenge, and it's exciting to be part of a culture that values creativity and problem-solving. What makes it even better is knowing that I'm solving meaningful problems alongside people who truly care about the work that we do and about each other."
John, Software Engineer

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
Vision insurance
Paid sick days
Home-office stipend for remote employees
In-person all-hands meetings
Flexible time off
Generous parental leave

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
In-person revenue kickoff
Employee-led culture committees
Mental health benefits
Continuing education stipend
Dental insurance
Paid industry certifications

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
Childcare benefits
Online course subscriptions available
Job training & conferences
Some meals provided
Promote from within
Recreational clubs

Above Lending

Financial Services + Fintech
About us
​​Above Lending, Inc. is a next-generation consumer lender. We provide our clients with simple and transparent products aimed to help them achieve their financial aspirations and take control of their debt. With competitive rates and personalized support from our loan specialists, our mission is to simplify the lending process and help borrowers ...
TOP PERKS + BENEFITS
Paid industry certifications
Relocation assistance
Hybrid work model
Life insurance
Flexible work schedule
Some meals provided

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
Job training & conferences
Hiring practices that promote diversity
Wellness programs
Home-office stipend for remote employees
Pair programming

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
Onsite office parking
Generous parental leave
Promote from within
Remote work program
Mother's room
Generous PTO

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
Hybrid work model
Unlimited vacation policy
Promote from within
Open office floor plan
401(K) matching
Onsite gym
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

Aeropay

Financial Services + Fintech
About us
Aeropay is America’s pay by bank network, making payments simpler and smarter for the digital economy.

Our integrated products and national network turn bank linking, money movement, and risk prevention into a seamless and reliable part of any payment experience.

Businesses of every size use Aeropay to lower payment ...
TOP PERKS + BENEFITS
Open office floor plan
Unlimited vacation policy
Day off for your birthday
Diversity employee resource groups
Mental health benefits
Quarterly engagement surveys

Prolaio

Analytics + Artificial Intelligence
About us
Prolaio is a clinical intelligence company dedicated to unlocking continuous, predictive and shareable heart data to liberate patients from hospital-based reactive care and accelerate every new therapy. The company was created by cardiologists, cardiovascular practitioners, and data scientists specifically to address the world’s number one cause ...
TOP PERKS + BENEFITS
Paid holidays
Mother's room
Bereavement leave benefits
401(K) matching
Generous parental leave
Remote work program

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
Continuing education available during work hours
Company-sponsored outings
Charitable contribution matching
Performance bonus
Company-sponsored happy hours
Disability insurance

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
Wellness days
Paid sick days
Employee awards
Employee-led culture committees
Mental health benefits
Home-office stipend for remote employees
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

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
Remote work program
Flexible Spending Account (FSA)
Open door policy
Lunch and learns
Team based strategic planning
Highly diverse management team
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
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
Paid industry certifications
Team based strategic planning
Disability insurance
Generous PTO
Personal development training
Paid holidays

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
Company sponsored family events
Paid sick days
Dedicated diversity and inclusion staff
Mentorship program
Generous PTO
Employee stock purchase plan
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
Team based strategic planning
Wellness programs
Onsite gym
Performance bonus
Paid holidays
In-person all-hands meetings
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
Disability insurance
Onsite gym
Dental insurance
Company equity
Open door policy
Paid sick days

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
President's club
Partners with nonprofits
Abortion travel benefits
Mental health benefits
Employee awards
Commuter benefits
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

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
Open office floor plan
Mandated unconscious bias training
Unlimited vacation policy
401(K)
Company-sponsored happy hours
Open door policy
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
Performance bonus
Floating holidays
Paid holidays
Mentorship program
Promote from within
Bereavement leave benefits

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
Flexible Spending Account (FSA)
Pair programming
Onsite office parking
Company equity
Disability insurance
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

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
Company-sponsored happy hours
Open office floor plan
Hiring practices that promote diversity
401(K) matching
Open door policy
Flexible Spending Account (FSA)
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
Highly diverse management team
Health insurance
Disability insurance
Vision insurance
Paid holidays
Promote from within

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
Job training & conferences
Family medical leave
Lunch and learns
Hiring practices that promote diversity
401(K)
OKR operational model

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
Flexible work schedule
Job training & conferences
Open office floor plan
Some meals provided
Vision insurance

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
Free snacks and drinks
Open door policy
OKR operational model
Mental health benefits
Diversity Program
Online course subscriptions available
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
Open door policy
Meditation space
Documented equal pay policy
Job training & conferences
Generous parental leave
Vision insurance

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
Health insurance
Team workouts
Diversity manifesto
Hiring practices that promote diversity
401(K) matching
Open office floor plan

Mode Mobile

AdTech + App development
About us
Mode Mobile is the creator of EarnOS, a transformational software that turns ordinary smartphones into "EarnPhones". This innovation empowers users globally to monetize everyday mobile activities such as streaming, gaming, shopping, etc. We enable users to profit from their data and attention, rather than letting only tech giants benefit ...
TOP PERKS + BENEFITS
Lunch and learns
Vision insurance
Employee-led culture committees
Commuter benefits
Generous PTO
Promote from within

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
Life insurance
Sabbatical
Generous PTO
Daily sync
Disability insurance
Continuing education stipend

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
Return-to-work program post parental leave
Pair programming
Team workouts
Continuing education available during work hours
Performance bonus
Pet insurance

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