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Work Remotely Jobs in Chicago, IL (NOW HIRING)

Primera Engineers, Ltd.

Mechanical Engineer

Chicago, IL · On-site +1

You'll enjoy flexibility to work remotely, work with great people, continue to learn and grow, and have a good time doing it. WHO WE ARE We value knowledge and learning. We believe in the power of ...

HMG Careers

Remote Life Insurance Agent

East Chicago, IN · Remote

$69K/yr

You will work remotely, serving clients by providing guidance and protection solutions for individuals and families. What We Offer * Remote, work-from-home career * Average first-year earnings of ...

New

Promoted2

Remote Insurance Agent

Chicago, IL · Remote

$69K/yr

You will work remotely, serving clients by providing guidance and protection solutions for individuals and families. What We Offer * Remote, work-from-home career * Average first-year earnings of ...

HMG Careers

Remote Customer Service and Sales

Harvey, IL · Remote

$69K/yr

You will work remotely, serving clients by providing guidance and protection solutions for individuals and families. What We Offer * Remote, work-from-home career * Average first-year earnings of ...

New

HMG Careers

Remote Benefits Sales Rep

Harvey, IL · Remote

$69K/yr

You will work remotely, serving clients by providing guidance and protection solutions for individuals and families. What We Offer * Remote, work-from-home career * Average first-year earnings of ...

New

Promoted2

Remote Insurance Agent

Joliet, IL · Remote

$69K/yr

You will work remotely, serving clients by providing guidance and protection solutions for individuals and families. What We Offer * Remote, work-from-home career * Average first-year earnings of ...

Promoted2

Remote Insurance Agent

Aurora, IL · Remote

$69K/yr

You will work remotely, serving clients by providing guidance and protection solutions for individuals and families. What We Offer * Remote, work-from-home career * Average first-year earnings of ...

Promoted2

Remote Insurance Agent

Elk Grove Village, IL · Remote

$69K/yr

You will work remotely, serving clients by providing guidance and protection solutions for individuals and families. What We Offer * Remote, work-from-home career * Average first-year earnings of ...

HMG Careers

Sales Executive - Remote

Harvey, IL · Remote

$69K/yr

You will work remotely, serving clients by providing guidance and protection solutions for individuals and families. What We Offer * Remote, work-from-home career * Average first-year earnings of ...

New

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Showing results 1-20

All JobsWork Remotely JobsWork Remotely Jobs in Chicago, IL

Work Remotely information

See Chicago, IL salary details

$21K

$79.8K

$150.9K

How much do work remotely jobs pay per year?

As of Aug 10, 2026, the average yearly pay for work remotely in Chicago, IL is $79,798.00, according to ZipRecruiter salary data. Most workers in this role earn between $48,754.00 and $99,562.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive in the work remotely position, and why are they important?

To excel while working remotely, you need strong self-motivation, time management, and digital communication skills, typically supported by proven experience in your field and a reliable internet connection. Familiarity with collaborative tools like Slack, Zoom, and project management platforms such as Asana or Trello is often required. Being highly organized, adaptable, and proactive in communication will set you apart in this environment. These skills are essential for maintaining productivity, ensuring clear collaboration, and delivering results without face-to-face supervision.

What are some common challenges of working remotely, and how can I overcome them?

Working remotely can present challenges such as staying motivated without direct supervision, managing potential feelings of isolation, and maintaining clear communication with your team. Setting up a dedicated and comfortable workspace, establishing a consistent daily routine, and making use of digital collaboration tools can help you stay productive and connected. It's also beneficial to proactively schedule regular check-ins and virtual meetings with colleagues to foster team cohesion. By developing these healthy habits, remote workers can create an efficient, engaged, and rewarding work experience.

What is a work remotely job?

A Work Remotely job is a position that allows employees to perform their tasks from outside a traditional office, usually from home or another remote location. These jobs typically utilize digital communication and collaboration tools to stay connected with teams. Remote work can be full-time, part-time, or freelance, depending on the employer and role. It offers flexibility but also requires discipline, time management, and self-motivation. Many industries, including tech, customer service, marketing, and writing, offer remote job opportunities.

What are the most commonly searched types of Work Remotely jobs in Chicago, IL? The most popular types of Work Remotely jobs in Chicago, IL are:
What are popular job titles related to Work Remotely jobs in Chicago, IL? For Work Remotely jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Work Remotely jobs in Chicago, IL look for? The top searched job categories for Work Remotely jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Work Remotely jobs? Cities near Chicago, IL with the most Work Remotely job openings:
Work Remotely jobs near you
Infographic showing various Work Remotely job openings in Chicago, IL as of August 2026, with employment types broken down into 2% Locum Tenens, 84% Full Time, 7% Part Time, and 7% Contract. Highlights an 100% Remote job distribution, with an average salary of $79,798 per year, or $38.4 per hour.

Life Insurance Agent-Work Remotely-Flexible Hours

GIA Legacy Planning

Chicago, IL • On-site, Remote

Full-time

Posted 5 days ago

Job description

Location: Remote Position/ Work from Home
Job Type: Full-Time/Part-Time
Compensation: 100% Uncapped Commission-Based
About Us:
We're excited to invite ambitious, self-driven individuals to join our dynamic team as Life Insurance Agents. This isn't a cookie-cutter job-it's a career built for people who want flexibility, purpose, and real earning potential. You'll have the freedom to work from anywhere, create a schedule that fits your life, and build a path toward financial independence.
This opportunity is perfect for career-driven professionals who want room to grow, sharpen leadership and business skills, and actually own their success. With clear growth opportunities and a performance-based model, you're not just clocking in-you're building a future that scales with your goals.
Responsibilities:
  • Identify client needs and recommend tailored insurance solutions
  • Develop and maintain strong client relationships
  • Generate leads through networking, referrals, and company-provided resources
  • Educate clients on available policies and coverage options
  • Follow up with prospects to close sales and maintain customer satisfaction
  • Stay informed about industry trends and product offerings
  • Work independently while collaborating with a supportive team

What We Offer:
  • Flexible work schedule (remote position)
  • Comprehensive training and mentorship programs
  • Access to top-rated insurance carriers and products
  • Opportunities for career growth and leadership development
  • Supportive team culture with ongoing coaching and professional development

Requirements:
  • Insurance license (or willingness to obtain one - we provide guidance)
  • Strong communication and interpersonal skills
  • Self-motivated with a results-driven mindset
  • Ability to work independently and manage time effectively
  • Basic computer skills for CRM and client management
  • Have technical device to conduct business: iPad. laptop etc.

Locations Chicago, IL Remote status Fully Remote

Apply