Best Companies to Work for in Chicago, IL (4,926)

Mission & Purpose: Helping people get out of debt is framed as a clear, motivating mission that many find meaningful. Client success stories and community programs reinforce a sense of purpose in daily work.

Compensation: Pay is considered strong in several roles, with sales and enrollment tracks citing high earning potential for consistent performers. Some functions describe competitive base pay paired with bonuses or commissions.

Benefits & Perks: Remote and hybrid options are available across multiple functions, alongside published benefits such as PTO, 401(k) match, and parental leave. Flexibility in work location is positioned as a practical advantage for candidates.

Benefits & Perks: Benefits are described as comprehensive, with healthcare, HSA contributions, wellness perks, generous PTO, and in‑office amenities. Feedback suggests the overall package is a strong part of the employment value proposition.

Work-Life Balance: A hybrid model enabling part‑week remote work and ample paid time off supports balancing work and personal commitments. Flex options such as parental leave and education reimbursement further reinforce flexibility.

Mission & Purpose: A member‑first, not‑for‑profit orientation and visible community involvement are consistently emphasized. This purpose‑driven stance is presented as integral to culture and decisions.

Market Position & Stability: The organization operates multiple leading grocery banners and continues investing in omnichannel and supply chain capabilities, signaling resilience and resources. Scale across brands enables mobility and can support steadier operations through industry cycles.

Benefits & Perks: Materials highlight comprehensive health coverage, retirement matching, paid parental leave, tuition support, wellness resources, and hybrid flexibility. Well-being programs and amenities are available at many offices.

Learning & Development: The company promotes on-demand learning, mentorship, leadership initiatives, internships/co-ops, and cross-banner moves. Structured programs and manager support for development are emphasized.

Mission & Purpose: Sustainability leadership—such as independently verified net‑zero targets and CarbonNeutral certification—sets the company apart in adtech. This purpose orientation is positioned as a draw for mission‑minded candidates.

Benefits & Perks: Offerings include 401(k) match, equity, flexible/remote options, learning stipends, generous leave, and wellness perks. Day‑to‑day extras like free meals, happy hours, and team outings contribute to a positive atmosphere.

Team Support: Colleagues are often described as collaborative, low‑ego, and quick to help, creating a friendly, productive environment. Inclusion programs and ERGs reinforce a sense of community and belonging.

Market Position & Stability: A long-established industry leader with healthy performance and visible product impact signals steadiness and brand strength. Feedback suggests the company’s scale and continuity provide stability and pride of impact.

Benefits & Perks: Broad medical coverage, retirement plans, paid time off, parental/adoption leave, tuition support, and assistance programs are emphasized, with union agreements delivering wage increases at covered sites. Feedback suggests total rewards are a core strength across many roles.

Career Growth: Structured rotational programs, leadership curricula, and formal training offer clear development paths across functions. Feedback suggests early‑career talent benefits from defined programs and mentorship with opportunities to build skills and move internally.

Mission & Purpose: Work centers on improving healthcare finance and decision support with visible, real‑world impact for hospitals and health systems. Feedback suggests mission-driven contributors find meaning in contributing to outcomes that matter to providers.

Team Support: Colleagues are often described as collaborative, helpful, and collegial, creating a supportive environment for problem‑solving and client work. Feedback suggests day‑to‑day teaming and peer relationships are a consistent bright spot.

Market Position & Stability: Being part of a larger software parent and operating as a leader in a defined vertical signals durable investment and long‑term orientation. Feedback suggests this context provides a sense of stability while maintaining mid‑size agility.

Mission & Purpose: Work at the intersection of payments and sectors like education and healthcare is described as meaningful and mission-driven. This aligns with candidates seeking impact in fintech.

Belonging & Inclusion: ERGs and “belonging” initiatives are prominently featured to support an inclusive, global culture. Visible programs such as Digital Disconnect Days and #InsideFlywire reinforce this emphasis.

Benefits & Perks: Compensation and perks include equity participation (RSUs/ESPP), paid health coverage, wellness benefits, and volunteer or disconnect days. Hybrid practices and opportunities for cross‑regional collaboration are also highlighted.

Benefits & Perks: Benefits include healthcare, 401(k) match, unlimited PTO, parental leave, remote/hybrid options, wellness resources, and work-from-home stipends. Published materials also describe first-day eligibility and flexible time off.

Market Position & Stability: Long tenure in EDI/iPaaS with a broad customer base and well-regarded products indicates a steady, mission-critical platform. Growth moves and acquisitions signal continued investment and scale.

Team Support: Colleagues are often seen as collaborative, supportive, and quick to help across functions, creating a welcoming, family-like environment. Open communication and approachable leaders are cited as enabling day-to-day teamwork.

Learning & Development: Structured programs like Belvedere Trading University, mock trading and theory courses, and formal mentorship enable rapid early-career ramp and ongoing skill growth. The firm also highlights a transparent, skills‑forward interview process and emphasis on empowerment and progression in a prop‑trading setting.

Work-Life Balance: The environment is often characterized as supportive and collaborative, offering balanced hours for the industry while accommodating market cadence. Office‑centric collaboration is paired with norms that many describe as closer to standard desk hours than at higher‑intensity peers.

Benefits & Perks: Comprehensive offerings include health insurance, a solid 401(k) match, PTO, parental leave, wellness programs, and commuter benefits, with interns receiving housing assistance and robust programming. Additional perks such as lunch stipends, fitness stipends, and company‑sponsored events are frequently highlighted.

Work-Life Balance: Colleagues often describe a healthy balance between work and personal life, with policies and norms that support time off and flexibility. Feedback suggests the day-to-day cadence and expectations enable sustainable workloads across many teams.

Benefits & Perks: Benefits are characterized as comprehensive—covering health coverage, retirement match, paid parental leave, mental-health days, and generous PTO—alongside professional development programs. Feedback suggests on-site and hybrid perks in Chicago add tangible value for those who prefer in-person collaboration.

Team Support: Colleagues are often seen as supportive, approachable, and collaborative, with managers who provide trust and guidance rather than micromanagement. Feedback suggests a people-first culture where individuals feel valued and can see the impact of their work.

Belonging & Inclusion: The company highlights an inclusion‑first approach with mature ERGs, social‑impact programs, and global community initiatives that signal a welcoming environment. Company materials describe active DEI programming and values that align with an inclusive culture.

Benefits & Perks: Offerings include equal paid parental leave, fertility and family‑forming support, mental‑health resources, 401(k) match, ESPP, flexible PTO, and hybrid/remote options. Job listings and benefits pages consistently describe comprehensive healthcare, financial, and time‑off programs.

Team Support: Colleagues are often seen as collaborative, kind, and supportive, with cross‑functional work and positive onboarding experiences. Managers are portrayed as invested in development and creating a welcoming environment.

Market Position & Stability: Financial momentum, including a board‑authorized repurchase and a planned stock split, signals confidence and stability. Broad enterprise adoption and scaled operations translate into resume value and perceived durability for many roles.

Innovation & Products: An AI‑first trajectory—deepened through partnerships like Anthropic and acquisitions such as Moveworks—demonstrates strong product velocity and relevance. Expanding identity and security capabilities reinforce the platform’s role across critical enterprise workflows.

Career Growth: Brand credibility with large enterprises and structured programs (e.g., ServiceNow University, RiseUp) support advancement across roles. Internal mobility and certifications help employees upskill toward higher‑value work as the platform evolves.

Work-Life Balance: Flexible hybrid arrangements, extra work-from-home days, and a remote-working allowance support manageable schedules and personal responsibilities. Feedback suggests this flexibility is central to the culture and fosters well-being and loyalty.

Team Support: Colleagues and leaders are often described as approachable and helpful, creating an employee-friendly environment. Feedback suggests teams collaborate well and encourage learning, skill development, and innovation.

Benefits & Perks: Comprehensive benefits such as retirement plans, health coverage, paid parental leave, generous time off, and wellness programs are frequently highlighted. Feedback suggests perks like volunteer time off, learning resources, and social events add to the overall package.

Work-Life Balance: Flexible practices such as remote/hybrid options and half‑day Fridays, paired with a results‑over‑location stance, support day‑to‑day balance. Policies and norms emphasize taking time when needed and maintaining wellbeing.

Learning & Development: Continuous investment in employee growth and self‑development is emphasized as a core operating principle. Structured opportunities and an expectation of ongoing learning reinforce skill‑building over time.

Recognition: Repeated placements on prominent workplace and industry award lists signal strong external validation of the employer experience. Certifications across regions and consecutive top rankings indicate sustained strengths rather than isolated wins.

Mission & Purpose: Many describe meaningful work that helps consumers save money while driving measurable profit for merchants, which makes the mission feel tangible. Company storytelling about major cash‑back milestones reinforces a sense of real‑world impact.

Career Growth: Opportunities to tackle challenging problems at scale and step up when the business is pushing hard are highlighted as accelerants for advancement. Strong individual contributors and high‑agency work environments can expand scope and skill development.

Benefits & Perks: Perks such as stock options, comprehensive health and mental health support, family‑forming benefits, and unlimited PTO are emphasized. Additional gestures like performance bonuses and recognition contribute to a supportive rewards environment.

Benefits & Perks: Published benefits include comprehensive health coverage, a 401(k) match, paid parental leave, and wellness, learning, and home‑office stipends. These offerings position the company competitively for a small, remote‑first adtech employer.

Work-Life Balance: Company materials emphasize a remote‑first setup with flexible schedules and autonomy over time off, complemented by hub meetups in Denver, Austin, and Chicago. This structure can support day‑to‑day flexibility for roles that thrive in asynchronous collaboration.

Recognition: External workplace accolades and certifications publicly associate the organization with a strong culture signal. Such recognition suggests recent efforts to invest in employee experience and employer brand.

Mission & Purpose: Work is portrayed as meaningful and consequential in real-time supply-chain visibility and control-tower software for major shippers across regions. The problems are described as technically interesting with tangible, real-world impact.

Benefits & Perks: Public materials highlight equity, hybrid flexibility, DEI groups, generous PTO and parental leave, wellness programs, and a 401(k) match with rapid vesting. Candidates are encouraged to verify specifics in offers, but signals suggest a comprehensive package.

Learning & Development: Offerings include customized development tracks, job training, conferences, mentorship programs, and supportive communities that promote continuous learning. There are significant opportunities to tackle complex problems and grow professionally.

Team Support: Colleagues are often described as smart, helpful, and low‑ego, creating a friendly environment with strong day‑to‑day interactions. The atmosphere is repeatedly characterized as collaborative with “great coworkers” and “no toxicity.”

Benefits & Perks: Compensation packages include profit sharing, comprehensive health coverage, retirement options, generous PTO, and notable in‑office perks like free meals and a subsidized gym. Multiple accounts highlight that these benefits and amenities materially enhance the overall experience.

Work-Life Balance: Engineering and trading‑technology roles are portrayed as offering reasonable hours for the industry alongside meaningful autonomy and fast paths to production. The balance is frequently contrasted favorably against peers with more intense schedules.

Work-Life Balance: Hybrid work, generous PTO, and a laid‑back environment are frequently highlighted. Colleagues point to remote flexibility and reasonable hours that support balance.

Learning & Development: Continuous learning is emphasized through hackathons, workshops, book clubs, conference support, and hands‑on internships. Feedback suggests interns and early‑career employees gain real project experience with mentorship.

Benefits & Perks: Health insurance options, 401(k) matching, parental and family supports, commuter benefits, snacks, and social events are prominently offered. Feedback suggests perks like education stipends, gym access, and catered food round out the package.

Mission & Purpose: The company focuses on modernizing independent paint, hardware, and building‑materials retailers with vertical software, supported by customer logos, case studies, and a partnership footprint that signal real‑world impact. Feedback suggests a clear, tangible mission with workflows beyond a prototype.

Benefits & Perks: Benefits include 100% employer‑paid employee medical/dental/vision, 401(k) with Betterment, equity, unlimited PTO with company holidays, daily team lunches, a fitness stipend, and learning/audiobook budgets. These offerings are consistently highlighted across job and careers materials for roles in Redwood City and Chicago.

Autonomy: Operations emphasize transparency and ownership through open backlogs, recorded calls, and rapid shipping where strong work quickly leads to more responsibility. Small‑team structure and fast iteration enable visible impact and hands‑on problem‑solving with real customers.