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

Team Support: Colleagues are often seen as friendly, collaborative, and supportive, creating a welcoming environment for new hires. Many describe strong cross‑team cooperation and a sense that people care about each other.

Benefits & Perks: Benefits are described as comprehensive, including retirement matching, bonuses, broad health coverage, generous PTO, paid volunteer time, and parental leave. Wellness programs and mental health support add to the overall package.

Work-Life Balance: Work pace is characterized as elevated yet reasonable, with remote or hybrid flexibility available in many roles. Unlimited PTO is considered accessible when performance expectations are met.

Learning & Development: The company emphasizes continuous learning and mentorship with early‑career pathways such as internships, micro‑internships, and an 18‑month trading track that provide hands‑on exposure and encourage employees to craft their careers.

Benefits & Perks: A comprehensive package includes health, dental and vision coverage, 401(k) matching, paid parental leave and adoption assistance, flexible PTO with sabbaticals, mental‑health resources, commuter benefits, company events, and stocked kitchens.

Recognition: Consistent placement on Built In Chicago’s Best Places to Work lists in recent years reflects external acknowledgment of compensation, benefits, flexible work, DEI initiatives, and people‑first programming.

Autonomy: Teams operate with high ownership under explicit principles that emphasize speed, direct communication, and iterative delivery. Feedback suggests this clarity and trust enable impactful, end-to-end work across functions and regions.

Work-Life Balance: Feedback suggests many employees experience reasonable balance supported by office-first collaboration enhanced with local perks and flexibility when needed. The combination of in-person support and autonomy helps some teams maintain sustainable routines.

Career Growth: Employees highlight opportunities to 'own their careers' and expand skills in a global setting with high-impact scope. Feedback suggests cross-market exposure and principle-led execution create meaningful learning and advancement for self-directed people.

Compensation: Pay is considered highly competitive across engineering, trading, and research, with strong total packages and top‑tier internships. Office perks and benefits (e.g., meals, wellness support, and retirement matching in some locations) reinforce the overall package.

Learning & Development: Structured graduate traineeships, technical courses (such as C++ and “Trading for non‑Traders”), and mentored ramp‑ups are emphasized. Early responsibility and tight trader‑engineer collaboration help new joiners ramp quickly.

Team Support: Culture is often described as smart, open, and collaborative, with quants, traders, and engineers working closely to ship ideas quickly. Social events, office‑centric community, and cross‑office collaboration further support a cooperative environment.

Market Position & Stability: Corporate backing from W. W. Grainger positions the business as scaled and financially durable, reducing existential risk compared with standalone startups. Recent investments such as the consolidated Chicago HQ and emphasis on the Endless Assortment segment signal ongoing commitment.

Benefits & Perks: Published offerings include day-one health coverage, paid parental leave, generous PTO, charitable matching, and a guaranteed employer 401(k) contribution, with equity available for certain roles. Additional perks like hybrid flexibility, remote Fridays, wellness programs, and development stipends are highlighted.

Work-Life Balance: A defined hybrid setup—two on-site days of choice with remote Fridays—provides predictability and flexibility for many office roles. Feedback suggests reasonable hours and a collegial environment in several functions, especially outside of high-volume support.

Benefits & Perks: Wellness stipends, mental health resources, flexible time off, and 'Refresh Days' are highlighted alongside comprehensive medical, dental, vision, and retirement programs. Recognition on 'Best Places to Work' lists reinforces the emphasis on supportive benefits and flexibility.

Career Growth: Advancement opportunities in a growing company are emphasized, with ongoing training, learning programs, and mentorship. Descriptions of visibility and learning in a smaller, scaling SaaS environment underscore prospects to develop.

Belonging & Inclusion: An inclusive culture is promoted through Employee Resource Groups and encouragement to bring authentic selves to work. Community-building and wellness initiatives are positioned to strengthen connection and support.

Mission & Purpose: Feedback suggests a focused niche in real-estate/property-management spend management and marketplace tooling gives clear problem alignment and operator-centric purpose. A defined vertical and ecosystem integrations make day-to-day work feel tangible.

Work-Life Balance: A hybrid setup with flexibility, including unlimited PTO and family-friendly time off, is emphasized. Feedback suggests some teams experience reasonable balance and autonomy in how work gets done.

Team Support: Colleagues are often seen as supportive and collaborative, with praise for great co-workers and a constructive, blame-free environment. Feedback suggests peer interactions are a consistent bright spot.

Market Position & Stability: The take‑private of SP+ established the company as the largest North American parking network with extensive airport operations, and later financings and leadership additions indicate meaningful resources and runway. This scale can support tooling, headcount, and expansion across many markets.

Innovation & Products: An AI/computer‑vision, checkout‑free platform deployed across real‑world sites offers tangible, high‑impact problems to solve. Examples include airport integrations and pricing features for constrained urban locations.

Autonomy: Engineering and HQ roles are described as high‑ownership with end‑to‑end shipping that directly touches operations. This environment enables rapid iteration and visible outcomes for builders comfortable with ambiguity.

Benefits & Perks: Compensation includes a rare employer‑funded pension alongside an employer‑matched 401(k), generous paid time off and family leave, wellness resources, and other perks. Total rewards are described as unusually strong compared with many private employers.

Mission & Purpose: Work ties directly to monetary policy support, bank supervision, economic research, payments, and community development. Many describe the work as meaningful and connected to public service impact.

Work-Life Balance: Many roles are characterized by reasonable hours, with flexibility or hybrid norms in some areas. Day‑to‑day expectations vary by team, but balance is frequently called out as a strength.

Benefits & Perks: Compensation and benefits are positioned as comprehensive, with 401(k) matching, equity grants, health coverage, flexible PTO, wellness stipends, and remote/hybrid options. Public materials also point to parental leave, childcare benefits, and home‑office support, signaling investment in employee well‑being.

Career Growth: Feedback suggests strong opportunities to take ownership and grow quickly in a lean, growth‑stage setting. Mentions of promoting from within, lunch‑and‑learns, and meaningful scope in engineering, data, product, and risk reinforce advancement potential.

Autonomy: Company messaging emphasizes trust, outcome‑focused management, and minimal micromanagement, enabling employees to manage their time and decisions. Flexibility and remote work programs indicate latitude in how and where work gets done.

Team Support: Colleagues are often described as genuine, helpful, and collaborative, with many looking forward to working with their teams daily. Peer recognition programs and team‑bonding activities reinforce a supportive atmosphere.

Benefits & Perks: Benefits begin on day one and include medical, dental, vision, paid time off (vacation, sick, holiday, birthday, volunteer, parental leave), wellness incentives, and retirement plans with matching. Professional development stipends and job training complement the core package.

Market Position & Stability: The company operates in a resilient insurance software niche with widely used, mission‑critical products and notable workplace accolades. This scale and industry focus provide a sense of stability and meaningful customer impact.

Benefits & Perks: Comprehensive benefits (health coverage, retirement matching, paid time off) and flexibility such as hybrid schedules are repeatedly highlighted. Feedback suggests these perks meaningfully support well‑being for many roles.

Compensation: Pay is considered competitive, with many citing strong salaries and bonuses relative to responsibilities. In manufacturing and union settings, overtime pay can further enhance earnings.

Learning & Development: Opportunities to learn and grow are emphasized through training, mentorship, and exposure to cross‑functional and international work. Early‑career pathways and on‑the‑job learning are seen as tangible strengths.

Benefits & Perks: Published benefits include fully covered vision, wellness stipend, generous PTO and parental leave, volunteer time, sabbaticals with tenure, and a generally three‑days‑onsite hybrid schedule. Additional perks such as commuter benefits, a monthly wellness subsidy, and support resources like EAP and One Medical are highlighted.

Market Position & Stability: The U.S. arm operates within a top global clearer serving 160+ venues, with Chicago and New York offices close to market infrastructure. Its status as a registered U.S. broker‑dealer with public filings and examinations signals a conventional, supervised environment.

Learning & Development: The company emphasizes professional growth through a continuing education stipend, job training, conferences, mentorship, paid certifications, and tuition reimbursement. Exposure to post‑trade workflows, risk, and international collaboration is described as valuable for building market‑structure expertise.

Benefits & Perks: Benefits are portrayed as comprehensive, including health coverage, 401(k) match, equity, stipends, daily lunches, and hybrid-friendly support, signaling material investment in employee well-being. Feedback suggests perks extend beyond basics to education support, mental health days, and flexibility that accommodates different life situations.

Work-Life Balance: Company materials emphasize flex-time, remote options, open vacation, sabbaticals, and explicit encouragement to take time off, indicating flexibility as a core norm. Feedback suggests time-off practices and flexible scheduling are actively encouraged rather than just stated.

Autonomy: The environment is framed as small-team with ownership where individuals can enact change and see visible impact. Feedback suggests self-starters have room to shape ideas and contribute directly in a lean, product-focused setting.

Benefits & Perks: A hybrid‑first setup and comprehensive benefits are prominently offered, including flexible time off, parental leave, tuition assistance, wellness resources, and programs like 401(k) match and ESPP. These benefits are consistently highlighted across materials and regions.

Market Position & Stability: The company operates as a large‑scale data/fintech leader with strong recent financial performance and ongoing external recognition. This scale provides ample data problems to solve and cross‑functional exposure.

Belonging & Inclusion: Associate resource groups and visible DEI programs are emphasized, with external recognitions in multiple regions reinforcing credibility. Inclusion infrastructure is clearly presented in employer materials and career pages.

Mission & Purpose: A clear, investor‑first mission and independent research focus give work meaningful industry impact through widely used products and content. The purpose‑driven ethos is consistently highlighted across roles and business lines.

Work-Life Balance: Hybrid schedules, reasonable hours, and generous time‑off programs—including sabbaticals—support balanced workloads in many teams. Flexibility and predictable rhythms are regularly emphasized as strengths.

Learning & Development: Structured programs, education stipends, mentoring, and rotational opportunities provide tangible pathways to build skills, especially for early‑ and mid‑career talent.

Mission & Purpose: The work centers on an options- and futures-focused mission that blends a brokerage with always‑on education, which appeals to builders who want to serve active retail traders. The media‑plus‑platform model creates visible, end‑user impact for product and content teams.

Benefits & Perks: Chicago offices highlight daily catered lunches, stocked kitchens, an onsite gym, commuter benefits, and a comprehensive benefits package including health coverage, PTO, and parental leave. The hybrid setup and in‑office amenities reinforce an in‑person, collaborative culture.

Market Position & Stability: Backing from a larger parent (IG Group) with continued investment in Chicago offices and studios signals support and growth. Parent integration provides resources and scale while maintaining the brands’ derivatives focus.

Market Position & Stability: Long operating history in mobile engagement, Tier‑1 aggregator positioning, and a roster of recognizable consumer brands signal durable product–market fit and operational continuity.

Benefits & Perks: Publicly listed offerings include flexible time off, an additional holiday week, parental leave, 401(k) match, and wellness and home‑office stipends alongside learning stipends, indicating an above‑baseline package for a mid‑sized firm.

Learning & Development: Core values emphasize "Always be Learning," with internal and external workshops, tuition assistance, and examples of internal mobility supporting skill growth and career progression.

Benefits & Perks: Benefits include comprehensive healthcare, 401(k) match, learning stipends, ERGs, generous parental leave, wellness stipends, and periodic company-wide days off. Hybrid flexibility and remote options further complement the total rewards package.

Work-Life Balance: Hybrid policies with remote options and flexible time off (including extra company “Chime Days”) help many roles manage personal and professional commitments. Location-aware flexibility across hubs like San Francisco and Chicago supports balance for office‑proximate and remote employees.

Mission & Purpose: Work centers on helping people achieve financial progress with explicit values such as “member‑obsessed,” “win together,” and “be an owner,” which can be motivating. Recognition rituals and community involvement reinforce this sense of purpose for teams.

Learning & Development: Sales training is often described as thorough and hands-on, with mentorship and structured onboarding that help newcomers ramp quickly. Opportunities to explore departments and build logistics knowledge enable rapid skill growth early on.

Team Support: Colleagues are frequently described as welcoming and supportive, creating a fun, high-energy office environment with events and social connection. Managers in several teams are portrayed as caring about employee success and willing to help.

Career Growth: Entry-level roles are framed as launchpads to learn fast and advance, with clear sales tracks and earning potential that can increase as performance scales. Internal promotions and mobility opportunities are highlighted for strong performers.