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Remote System Administrator Jobs in Chicago, IL (NOW HIRING)

Elase Nationwide

Business System Manager

Wheaton, IL · On-site +1

$65 - $100K/hr

Bachelor's degree required * 2+ years as a systems admin required * POS experience and proficiency ... This position is remote and you must live in one of the states we currently operate in. CO, ID, AZ ...

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Remote System Administrator information

See Chicago, IL salary details

$42.2K

$91.6K

$141.6K

How much do remote system administrator jobs pay per year?

As of Aug 31, 2026, the average yearly pay for remote system administrator in Chicago, IL is $91,608.00, according to ZipRecruiter salary data. Most workers in this role earn between $72,100.00 and $107,100.00 per year, depending on experience, location, and employer.

What is a remote system administrator?

A Remote System Administrator is responsible for managing and maintaining IT systems, servers, and networks from a remote location. They ensure system performance, security, and updates while troubleshooting technical issues. This role often involves configuring hardware and software, monitoring system health, and responding to outages or cyber threats. Remote System Administrators typically use remote access tools and cloud-based solutions to perform their tasks efficiently. They play a crucial role in keeping an organization's IT infrastructure operational and secure.

What are the typical daily responsibilities of a remote system administrator?

As a Remote System Administrator, your daily tasks often include monitoring servers and network performance, applying updates and patches, managing user permissions, and responding to support tickets or incidents. You'll routinely perform system backups, ensure data security, and coordinate with other IT staff or departments to troubleshoot and resolve technical issues. Regular communication via email, chat, or video calls is common when collaborating with team members or supporting users. This role requires both proactive maintenance and reactive problem-solving to keep IT environments running smoothly.

What are the key skills and qualifications needed to thrive in the remote system administrator position, and why are they important?

To thrive as a Remote System Administrator, you need a solid background in computer networking, server management, troubleshooting, and information security, often demonstrated by a degree in computer science or a related field. Familiarity with tools such as Linux/Windows server environments, virtualization platforms, cloud services (like AWS, Azure), and certifications like CompTIA Server+, Microsoft, or Cisco are highly valued. Strong problem-solving skills, clear communication, and the ability to work independently are crucial soft skills in this role. These competencies ensure reliable system uptime, quick issue resolution, and effective collaboration with distributed teams in dynamic IT environments.

What are the most commonly searched types of System Administrator jobs in Chicago, IL?

The most popular types of System Administrator jobs in Chicago, IL are:

What are popular job titles related to Remote System Administrator jobs in Chicago, IL?

For Remote System Administrator jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote System Administrator jobs in Chicago, IL look for?

The top searched job categories for Remote System Administrator jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote System Administrator jobs?

Cities near Chicago, IL with the most Remote System Administrator job openings:

Remote System Administrator jobs near you
Infographic showing various Remote System Administrator job openings in Chicago, IL as of August 2026, with employment types broken down into 82% Full Time, 12% Part Time, and 6% Contract. Highlights an 100% Remote job distribution, with an average salary of $91,608 per year, or $44 per hour.

Benefits Administrator (Dayforce)

Addison Group

Chicago, IL • Remote

$35 - $40/hr

Contractor

Medical, Dental, Vision, Life, Retirement

Re-posted 18 days ago

Job description

Job Title: Benefits Administrator (Dayforce)

Industry: Insurance

Location: Remote (U.S.)

Assignment Type: Contract – Approx. 6 months

Pay: $35.00–$40.00 per hour

Work Schedule: Monday–Friday, 8:30 AM–5:00 PM CST

Benefits: This position is eligible for medical, dental, vision, and 401(k).

About the Company:

Our client is a nationally recognized organization in the insurance and employee benefits industry that partners with businesses to deliver comprehensive HR, benefits, retirement, and risk management solutions. They are known for fostering a collaborative culture, leveraging innovative technology, and providing exceptional service to both employees and clients.

Job Description:

Addison Group is partnering with our client to identify an experienced Benefits Administrator to support a high-volume benefits team during the annual open enrollment season. This fully remote contract opportunity is ideal for someone with strong HRIS experience, advanced Excel skills, and a customer-focused approach to benefits administration.

In this role, you will assist employees with benefit-related questions, maintain accurate enrollment data, troubleshoot system issues, reconcile benefit information, and collaborate with internal teams to ensure a smooth open enrollment process.

Key Responsibilities:

  • Administer employee benefit enrollments and maintain accurate records within Dayforce and other HRIS platforms.
  • Support annual open enrollment by reviewing benefit configurations, testing enrollment workflows, and validating system functionality.
  • Respond to employee inquiries regarding medical, dental, vision, life, disability, FSA/HSA, and voluntary benefit plans.
  • Assist employees with eligibility questions, qualifying life events, dependent verification, and enrollment changes.
  • Research and resolve benefit-related issues while coordinating with payroll, HR, insurance carriers, and external vendors.
  • Audit enrollment data, payroll deductions, carrier files, and eligibility reports to identify and correct discrepancies.
  • Process benefit-related transactions, including evidence of insurability requests, leave-related benefit updates, benefit arrears, and dependent age-out tracking.
  • Create and maintain reports using Excel, including PivotTables and VLOOKUPs, to support audits and reconciliation efforts.
  • Prepare employee communications, benefit guides, and documentation while maintaining detailed tracking logs.
  • Participate in project meetings and assist with post-enrollment audits, reconciliations, and process improvements.

Qualifications:

  • Previous experience administering employee benefits in a high-volume environment.
  • Hands-on experience with Dayforce is required.
  • Advanced Microsoft Excel skills, including PivotTables and VLOOKUPs.
  • Strong understanding of employee benefits, eligibility requirements, enrollment rules, dependent verification, and leave-related benefit administration.
  • Excellent problem-solving and analytical abilities with exceptional attention to detail.
  • Outstanding customer service, written communication, and interpersonal skills.
  • Ability to prioritize multiple deadlines while maintaining accuracy in a fast-paced environment.
  • Comfortable handling confidential employee information with professionalism and discretion.

Additional Details:

  • 100% remote position.
  • This position supports a busy benefits team during a critical open enrollment period.

Perks:

  • Fully remote work environment.
  • Opportunity to gain experience with a well-established national organization.
  • Collaborative and supportive team culture.
  • Exposure to enterprise-level HRIS and benefits administration systems.
  • Meaningful project work supporting annual open enrollment initiatives.
Addison Group is an Equal Opportunity Employer. Addison Group provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state and local laws. Addison Group complies with applicable state and local laws governing non-discrimination in employment in every location in which the company has facilities. Reasonable accommodation is available for qualified individuals with disabilities, upon request.