Senior Systems Administrator Jobs in Chicago, IL
Senior Systems Administrator jobs in Chicago are in strong demand, concentrated in the Loop, River North, and the Fulton Market tech corridor, across healthcare, financial services, and enterprise technology. Employers hiring right now include PwC, United Airlines, and Huron Consulting. Scan the live roles below and apply to whichever ones fit.
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- Permanent - Full Time
- Chicago
Key Responsibilities
Technical Triage & Optimization: Act as the ultimate escalation point for complex technical issues, system bugs, and synchronization errors. Triage integration data mismatches and “break-fix” scenarios with internal IT and external vendor support teams.
Compliance & Governance: Ensure all financial systems and custom workflows strictly comply with internal controls, SOX compliance guidelines, IT General Controls (ITGC), and standard data privacy regulations.
Business Partnership & Roadmap: Collaborate closely with accounting, FP&A, procurement, and sales ops teams to translate complex business requirements into scalable technical solutions and system enhancements.
Automation & Scripting: Support and optimize existing automation scripts (SuiteScript, Python, JavaScript) and middleware tools (e.g., MuleSoft) to reduce manual accounting work and streamline the month-end close process.
Skills, Knowledge and Expertise
Benefits
Compensation: $144,000 – $219,000 / year
- Health & Financial Security:
- Medical, Dental, and Vision insurance
- Flexible Spending Accounts (FSA) & Health Savings Accounts (HSA)
- 401(k) retirement plan
- Pre-tax transit and parking benefits
- Time Off & Flexibility:
- Enjoy the best of both worlds: the energy and collaboration of in-person work, combined with the convenience and focus of remote days. This is a hybrid position requiring three days of in-office collaboration per week, with the flexibility to work remotely for the remaining two days. Our hybrid model is designed to balance individual flexibility with the benefits of in-person collaboration, enhanced team cohesion, spontaneous innovation, hands-on mentorship opportunities and strengthens our company culture.
- 22 days of Paid Time Off (PTO) per year, with the option to roll over unused days.
- One dedicated day per year for volunteering.
- Two professional development days per year to allow uninterrupted professional development.
- An additional PTO day added during milestone anniversary years.
- Robust paid holiday schedule with early dismissal.
- Generous parental leave for all parents (including adoptive parents).
- Work-Life Support & Resources:
- Budget for tech accessories, including monitors, headphones, keyboards, and other office equipment.
- Backup child and pet care, as well as tutoring services.
- Milestone anniversary bonuses.
- Wellness & Lifestyle Perks:
- Stipend and subsidy contributions toward personally-owned cell phones
- Contributions for gym memberships and health/wellness initiatives.
- Discounted healthcare premiums.
- Healthy meal delivery program subsidies.
Trading Technologies (www.tradingtechnologies.com) is a global capital markets platform services company providing market-leading technology for the end-to-end trading operations of Tier 1 banks, brokerages, money managers, hedge funds, proprietary traders, Commodity Trading Advisors (CTAs), commercial hedgers, and risk managers. With its roots in listed derivatives, the Software-as-a-Service (SaaS) company delivers “multi-X” solutions, with “X” representing asset classes, functions, workflows, and geographies. This multi-X approach features trade execution services across futures and options, fixed income, foreign exchange (FX), and cryptocurrencies, augmented by solutions for data and analytics, including transaction cost analysis (TCA); quantitative trading; compliance and trade surveillance; clearing and post-trade allocation; and infrastructure services. The award-winning TT platform ecosystem also helps exchanges deliver innovative solutions to their market participants and technology companies to distribute their complementary offerings to Trading Technologies’ clients.
Trading Technologies (TT) is an equal-opportunity employer. Equal employment has been, and continues to be, a required practice at the Company. Trading Technologies’ practice of equal employment opportunity is to recruit, hire, train, promote, and base all employment decisions on ability rather than race, color, religion, national origin, sex/gender orientation, age, disability, sexual orientation, genetic information, parental status, veteran, or any other protected status. Additionally, TT participates in the E-Verify Program for US offices.
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Find JobsSenior Systems Administrator Job Market in Chicago
Who's Hiring
- PwC4

- United Airlines4

- Huron Consulting4

- Boston Consulting3

- EY2

Top Industries Hiring
- Consulting & Professional Services16
- Technology & Software9
- Accounting & Auditing7
- Investment & Asset Management7
- Healthcare & Medical Services5
Senior Systems Administrator Jobs in Chicago: Frequently Asked Questions
How do I get a senior systems administrator job in Chicago?
The strongest path is targeting Chicago's dense concentration of large healthcare systems, financial services firms, and enterprise technology companies in the Loop and Fulton Market district. Hands-on experience with hybrid cloud environments, Active Directory, and network infrastructure stands out with local employers. Certifications like Microsoft MCSA, Cisco CCNA, or CompTIA Server+ carry real weight, and networking through Chicago-area IT user groups helps surface roles before they're widely posted.
Which companies hire senior systems administrators in Chicago?
Chicago senior systems administrator roles are posted by PwC, United Airlines, and Huron Consulting and others right now, based on current listings on Migrate Mate as of June 2026. Chicago's employer base runs wide, from major health networks and global financial institutions headquartered downtown to mid-size managed service providers and enterprise software firms spread across the metro area.
Are there remote senior systems administrator jobs in Chicago?
Yes, though selectively, since senior systems administrator work often requires hands-on access to servers, network hardware, and on-site infrastructure. About 30% of senior systems administrator openings tied to Chicago are remote or hybrid as of June 2026, with remote arrangements most common for roles focused on cloud administration, monitoring, and documentation rather than physical data center management.
How can I get a senior systems administrator job in Chicago with little or no experience?
The most realistic entry path in Chicago is starting as a junior systems administrator or IT support specialist at one of the city's many mid-size managed service providers, which tend to offer broader exposure than large enterprises. Chicago's healthcare and university sectors also hire entry-level infrastructure staff who rotate across systems. Building lab experience with virtualization platforms and earning a foundational certification like CompTIA A+ or Network+ makes a candidate more competitive locally.
Which industries hire the most senior systems administrators in Chicago?
Most senior systems administrator openings in Chicago sit in Consulting & Professional Services, Technology & Software, and Accounting & Auditing, per current listings on Migrate Mate as of June 2026. Chicago's role as a hub for commodities trading, insurance, and regional healthcare systems drives consistent infrastructure staffing needs across those sectors year-round.
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