Best Midsize Companies to Work For in Chicago in 2026

"The work life balance at pricefx is one of the best I've had in my career. My team understands that having two young children takes a lot of time outside the typical 9-5 hours. "

"It depends on where we are in a given release cycle. We operate under an Agile SDLC, so there's many different pieces of the puzzle you could be on any given day - every day is different. But at the end of the day our developers are really being hands-on and implementing business features that can go out to our customers on a regular basis."

"The people at Smartly have all different backgrounds and areas of expertise, but what ties us all together is a deep passion for solving customer problems. This common ground creates a fun, collaborative and solution-oriented environment to work in!"

"Building something completely new is challenging, satisfying work, and I am proud of what we’re building here at Upside. Our product is making a real, measurable impact on people and businesses, and the team behind the scenes is beyond compare. If you want to work at a company that’s doing well while doing good, Upside should be high on your list."

"Remote-first allows for more time for the things that matter to employees. Not commuting to an office (unless you count walking to the spare room I work in) leaves so much time for things that fulfill my life outside of work, which then fuels the way I show up to work. "

"Vivid Seats opens the door for your advancement. It is up to everyone to use the tools given and carve their own path. Coupled with a rapidly growing environment, working at Vivid Seats is an opportunity worth taking."

"Working at Belvedere is great for someone who values learning and innovation! Belvedere always encourages me to follow my interests and encourages inter team collaboration to help employees improve their skillsets as well as improve on our culture as a whole! "

"I love working for Basis because I’m surrounded by open, honest, and intelligent people who constantly inspire me. The healthy work-life balance allows me to thrive both personally and professionally, and the freedom to test new ideas without fear of failure fosters continuous growth and innovation."

"To be a part of PatientPoint, creating products that are connecting with patients which could impact their health journeys, their quality of life and their human existence is one of the most powerful contributions I’ve made in my career."

"I believe the work we are doing here at VelocityEHS is positively impacting workers across the globe. Nothing excites me more when our customers share how all of their hard work is improving workplace safety & culture. It's more than software, it's people, and we get to play a small part in making workplaces safer each day we show up. "

"I appreciate the amount of energy that goes into cultivating individuals here. Fusion shares my belief that people are the most important investment and the willingness to support personal growth is unmatched by any other company I've worked for."

"I’ve really enjoyed my time at Vail because of Vail’s dedication to bettering their product by bettering their engineers. Continuous learning is supported via book clubs, self-learning programs, and biweekly meetings to share new ideas and technology"

"What I love most about working at Vibes is the culture. The people here are so helpful and everyone is treated with respect. Opinions are heard and valued. Hard work is acknowledged. The company cares about its employees, and it shows!"

"The most fulfilling aspect of my role is the meaningful influence my opinions carry and the direct impact I can have on shaping the future of the company. This collaborative environment ensures that every team member's viewpoint, including mine, is not only recognized, but valued. "

"The moment I started at Lessen, I was impressed with the continuous effort to improve the culture in the office. From creating space via forums where individuals can realize their full potential as they are to fantastic events that build trust, togetherness, and just plain fun!"

"I was so excited to join a team that welcomed me with open arms and has helped get me ramped up quickly. I appreciate how people are quick to raise their hands and take ownership of different projects. "

"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. "

"Whenever someone asks me what I love most about Strata, my answer always starts with the creative freedom I get as an engineer. Innovation is one of our core engineering principles and we have a culture that embraces communication and sharing ideas."

"I started at Wolverine fresh out of college. What I discovered was a technology driven culture that encouraged me to explore. Wolverine has opened doors to places I didn’t even know existed. And no one stands in the way of a good idea."

"My favorite part of Hireology’s culture is our high-trust teams. We share information easily, we extend support to one another, we’re not afraid to take up challenging work, and we don’t worry about other team members letting us down. "

"The culture at OpenX is unmatched! While our teams work diligently in supporting our business goals, everyone at OpenX also works authentically in helping each other reach their individual goals."

"The people at Bringg make me feel I can bring my genuine self to work each day. I feel adequately challenged, supported, and appreciated. The people I’ve encountered here are some of the most passionate and high-energy people I’ve been around."

"Although I have an open-door policy, being in my office creates a barrier to communication. I remedy this by spending 2-3 days a week working at a random desk within one of the operations teams. On that day, I join day-starts, ask questions on work flows and subject the teams to my never-ending stream of dad jokes."

"OppFi's employees thoroughly enjoy celebrating each other's accomplishments, fostering a profound sense of camaraderie and connection, even when physically apart. The clear impact of feeling celebrated and supported by our colleagues, regardless of physical proximity, serves as a powerful inspiration to show up as our authentic selves."

"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."

"Arity’s culture is unbeatable. After years of working in a typical corporate environment, I moved to Arity and immediately fell in love with the collaborative nature. My work is valued, I have autonomy, and I am on one team working towards one goal."

"Alliant fosters an inclusive and supportive workplace by embracing the totality of the human experience, acknowledging that personal experiences are strengths that can be leveraged to serve members and identify business needs."

"The autonomy with which I collaborate with people across our growing company is my favorite aspect of being on the Zoro team. I have the trust and freedom to solve fun problems daily with experts in engineering, design, supply chain, marketing, architecture, and dozens more. The bonus is having the privilege to be my true self in every interaction."

"The diversity of characteristics that make up our team is what makes Avant great. We proactively explore ways to play to the strengths and uniqueness of our culture and stay connected whether Avantees are in person or remote. We are working hard to preserve the key elements of our culture — which are centered around relationships — as we scale."

"My skills and opinions are valued at Analytics8. I love that I am continually learning and growing my skill set."

"Simplex is the perfect fit because of its streamlined, tech-first culture. I get to focus on what matters most without jumping through hoops. "

"Leaving my previous job after nearly 9 years was a really difficult decision but the transition was easy largely due to the incredibly supportive team members here at FourKites. I am grateful everyday to be able to work with such professionals."

"We’re in a fast-paced industry, but no matter how busy people get, no one’s ever too busy to help a colleague out. We’re surrounded by smart, driven people and the collaboration amongst the teams is the reason why we are constantly growing. Plus, there’s free food and puppies to get you through the day!"

"At Clear Street, everyone wants to succeed both individually and as a company. I have the rare opportunity to work towards building a business from the ground up. Plus, I’m working alongside some of the best people in the industry."

"I've always felt supported as a person. Growth isn't just encouraged, it's built into the culture. I regularly receive opportunities to take on new challenges and expand my skill set."

"Dscout hosts monthly ‘Tuesday Teas’ where a teammate leads a discussion about a topic they are passionate about. Last month an engineer led a talk on the French Revolution, and earlier a lead researcher spoke about brewing beer... It's a fun way to learn about our peers and about something we may have never thought to learn more about!"

"Hearing the reactions of clients when the platform delivers beyond their expectations is inspiring. The product and dev teams empower our clients with the most sophisticated capabilities they can leverage, while keeping the interface incredibly easy."

"I’m grateful that at Attain I get to work alongside some of the brightest and most genuine colleagues I’ve ever met. We push each other to do our best work every day. Attain proves that ambition, innovation, and kindness aren’t opposites - they’re strongest when they work together."