Top Chicago, IL Companies With Unlimited PTO (248)

Adyen (ADYEN:AMS) is the financial technology platform of choice for leading companies. By providing end-to-end payments capabilities, data-driven insights, and financial products in a single global solution, Adyen helps businesses achieve their ambitions faster. With offices around the world, Adyen works with the likes of Meta, Uber, H&M, eBay, and Microsoft.

Alliant is unlike any other financial institution — a digital credit union that wows our members. We’re boldly disrupting banking norms to do good for our members, employees and communities. With 90 years of history and more than $19 billion in assets, Alliant Credit Union is the largest credit union in Illinois and one of the largest in the U.S. Our industry-leading...

Built In is the AI-powered career platform that connects innovative companies with professionals navigating their careers in a world reshaped by AI. For candidates, we provide AI-driven job recommendations and resources that support smarter career decisions. For employers, we deliver the always-on recruitment and reputation platform that ensures your brand is visible, trusted, and chosen. By combining employer brand insights,...

At Braze, we believe in the passion of our people. We seek to ignite that passion by setting high standards, championing teamwork, and creating work-life harmony. We thrive when people add their unique perspectives to our ever-growing teams—and we strive to empower you to make an impact that fuels both you, and our business.

Block, Inc. is a global technology company with a focus on financial services. Made up of Square, Cash App, Afterpay, TIDAL, Bitkey, and Proto, Block, Inc. builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the...

Attain is the most trusted and comprehensive source for permissioned, real-time purchase data in the United States. By connecting directly with over 10 million consumers, Attain delivers unmatched accuracy and scale across audience activation, insights, and in-flight optimization, and measurement, helping marketers tie every dollar of media to real-world sales outcomes. Attain’s portfolio of owned and operated apps, spanning financial...

Enverus’ innovative technologies drive production and investment strategies, enable best practices for energy and commodity trading and risk management, and reduce costs through automated processes across critical business functions. Enverus is a strategic partner to more than 6,000 customers in 50 countries. Enverus is a portfolio company of Hellman & Friedman and Genstar Capital.

Taboola empowers businesses to grow through performance advertising technology that goes beyond search and social and delivers measurable outcomes at scale. Taboola works with thousands of businesses who advertise directly on Realize, Taboola’s powerful ad platform, reaching approximately 600M daily active users across some of the best publishers in the world. Publishers like NBC News, Yahoo, and OEMs such as Samsung,...

Halo Investing is an award-winning technology platform that disrupts how protective investment solutions are used worldwide. Headquartered in Chicago, with employees worldwide, we’re on a mission to change the world by democratizing access to investment solutions that were previously unavailable to most investors. Our marketplace connects financial advisors and investors to protective investment products – including structured notes and annuities...

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 who can bring their ideas...

Bellagent is an enterprise-level AI agent platform built to automate everyday business operations with zero-touch integrations that connect instantly to more than 1,300 applications. Launched in 2025 by Proactifi Inc., and headquartered in Chicago, the platform is built for practicality with industry-leading compliance and security standards, enabling organizations to deploy AI agents without friction from day one. Bellagent’s mission to...

We're a global community of bold visionaries and resourceful doers who are shaping the future of Dropbox—and with it the future of work. Our Virtual First model combines the flexibility of a distributed workplace with the power of human connection, making space for both meaningful work and meaningful relationships. With our start-up mindset and enterprise-level opportunities, you can be who...

EliseAI builds vertical AI agents for housing and healthcare — sectors that together make up nearly 40% of household spending. These agents automate high-volume workflows like leasing, maintenance, renewals, and patient intake, helping organizations cut costs, improve efficiency, and deliver better experiences. How does it work? EliseAI integrates directly into operational workflows: Housing: Manages leasing, maintenance, renewals, billing, and resident communication. Healthcare: Handles intake,...

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 use it...

Basis is a leading global provider of automation software designed specifically for enterprise marketers. Our platform, Basis, is the industry’s only comprehensive digital media solution that seamlessly integrates programmatic, site-direct, advanced TV, search, and social media within a single interface. By unifying these functions, Basis simplifies complex and disconnected media operations, automates repetitive tasks, and minimizes manual processes, enabling marketing...

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 the most out of their existing technology. But it’s not...

We contribute to human progress by empowering people to express themselves, live in the moment, learn about the world, and have fun together.

Upside is a technology company that increases the financial power of people and businesses in the real world. Our technology has helped millions of people get more purchasing power on the things they need, and tens of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year, and that value goes...

Over the last 15 years, we’ve grown from a startup to a market-leading organization with over 150 team members, and we’ve created an award-winning culture that makes this company an amazing place to work. We've been ranked on multiple best places to work lists including the 2026 BuiltIn Chicago rankings.

At Toro TMS, we are on a mission to deliver technology that drives lasting improvements for the trucking industry. Our dedicated team has built an easy-to-use, modern end-to-end TMS specifically designed for bulk haulers. From load management and dispatch, to accounting and driver payroll, we provide a single software solution to help our customers move more loads.