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Remote Work Own Schedule Jobs in Chicago, IL (NOW HIRING)

True North Recruiters

Let's Get to Work

Chicago, IL · Remote

$105K - $137K/yr

Remote (Work From Anywhere) Compensation: 100% Commission -- Uncapped Income Potential Experience ... Manage your own schedule and pipeline -- you're the CEO of your business * Continuously grow your ...

Symmetry

Remote Sales Work From Home

Chicago, IL · On-site +1

Insurance Producer - 100% Remote Must be authorized to work in the US, no work visas offered at ... Set Your Own Schedule * This Commission Only Position Starts at 80% and Goes to 130% With ...

Symmetry

Remote Sales Work From Home

Chicago, IL · Remote

Insurance Producer - 100% Remote Must be authorized to work in the US, no work visas offered at ... Set Your Own Schedule * This Commission Only Position Starts at 80% and Goes to 130% With ...

Nexera

Entry Level Remote Insurance Sales

Chicago, IL · Remote

$1.5K - $3.2K/wk

Year 5+: Lead a team, generate passive income, work your own schedule Most of our managers and team ... Raleigh/Triangle area preferred -- fully remote, open to all U.S. locations * Able to pass a ...

Nexera

Entry Level Remote Insurance Sales

Chicago, IL · Remote

$1.5K - $3.2K/wk

Year 5+: Lead a team, generate passive income, work your own schedule Most of our managers and team ... Raleigh/Triangle area preferred -- fully remote, open to all U.S. locations * Able to pass a ...

Pioneer Agency

Insurance Agent

Chicago, IL · Remote

$50K - $75K/yr

Work Location: Remote Schedule: Flexible hours; set your own schedule. If you are driven, coachable, and ready to embark on a new career path, we encourage you to consider this opportunity.

Learner Education

Online Science Tutor

Chicago, IL · Remote

$25/hr

What We Offer Flexible remote work environment Ability to set your own schedule High quality student referrals Supportive community of tutors for collaboration and growth Professional development ...

Learner Education

Online Science Tutor

Chicago, IL · Remote

$25/hr

Flexible remote work environment * Ability to set your own schedule * High quality student referrals * Supportive community of tutors for collaboration and growth * Professional development ...

Learner Education

Online Calculus Tutor

Chicago, IL · Remote

$25/hr

This is a fully remote contract role with flexible scheduling and consistent student demand. What We Offer Flexible remote work environment Ability to set your own hours High quality student ...

Learner Education

Online Calculus Tutor

Chicago, IL · Remote

$25/hr

This is a fully remote contract role with flexible scheduling and consistent student demand. What We Offer * Flexible remote work environment * Ability to set your own hours * High quality student ...

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All JobsWork Own Schedule JobsRemote Work Own Schedule JobsRemote Work Own Schedule Jobs in Chicago, IL

Remote Work Own Schedule information

See Chicago, IL salary details

$28

$33

$36

How much do remote work own schedule jobs pay per hour?

As of Aug 29, 2026, the average hourly pay for remote work own schedule in Chicago, IL is $33.11, according to ZipRecruiter salary data. Most workers in this role earn between $31.15 and $35.05 per hour, depending on experience, location, and employer.

What is a remote work own schedule?

A Remote Work Own Schedule job allows you to work from anywhere while setting your own hours. These roles often focus on results rather than a fixed schedule, offering flexibility to balance personal and professional commitments. Common industries for this type of work include freelance writing, virtual assistance, customer service, and online sales. However, some positions may require availability during specific hours for meetings or deadlines. It's important to stay self-motivated and manage your time effectively to succeed in this type of work.

What are the typical daily routines and work expectations for employees in a remote work own schedule position?

In a 'Remote Work Own Schedule' role, you'll generally have the flexibility to set your own hours, as long as deadlines and performance metrics are consistently met. Daily tasks and responsibilities will vary based on your specific job title, but staying organized and maintaining regular communication with your team or manager are usually essential. While you might work independently much of the time, you may also need to attend virtual meetings, provide regular progress updates, and collaborate using digital tools. This structure supports work-life balance, but it also requires you to be disciplined and accountable for managing your workflow and priorities.

What are the key skills and qualifications needed to thrive in a remote work own schedule position, and why are they important?

To succeed in roles advertising 'Remote Work Own Schedule,' you need excellent time management, self-motivation, and the relevant professional expertise required for the specific job function. Familiarity with remote collaboration tools like Slack, Zoom, and project management platforms such as Trello or Asana is often necessary. Outstanding communication, adaptability, and proactive problem-solving are valuable soft skills in these settings. These qualities are crucial for meeting goals independently, maintaining productivity, and collaborating effectively across virtual teams.

What are the most commonly searched types of Work Own Schedule jobs in Chicago, IL?

The most popular types of Work Own Schedule jobs in Chicago, IL are:

What are popular job titles related to Remote Work Own Schedule jobs in Chicago, IL?

For Remote Work Own Schedule jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote Work Own Schedule jobs in Chicago, IL look for?

The top searched job categories for Remote Work Own Schedule jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote Work Own Schedule jobs?

Cities near Chicago, IL with the most Remote Work Own Schedule job openings:

Remote Work Own Schedule jobs near you
Infographic showing various Remote Work Own Schedule job openings in Chicago, IL as of August 2026, with employment types broken down into 87% Full Time, and 13% Part Time. Highlights an 100% Remote job distribution, with an average salary of $68,862 per year, or $33.1 per hour.

Let's Get to Work

True North Recruiters

Chicago, IL • Remote

$105K - $137K/yr

Full-time

Posted 4 days ago

Job description

Life & Annuity Insurance Sales Agent — 100% Remote | 100% Commission | Unlimited Earning Potential

Location: Remote (Work From Anywhere) Compensation: 100% Commission — Uncapped Income Potential Experience Level: All levels welcome — experienced agents and motivated newcomers

? Watch This First: "Let's Get to Work"

Before you read another word, watch this short video to see exactly what this opportunity is about and why now is the time to join us:

▶️ WATCH: "Let's Get to Work"

About Taubman Financial Management

For over 30 years, Taubman Financial Management (TFM) has helped families, individuals, and businesses find real financial peace of mind. Backed by cutting-edge technology and access to more than 60 top carriers, TFM gives you the tools to deliver real solutions — not just policies. Join us, and we'll help you level up your game, unlock your earning potential, and build the life you actually want for you and your family.

Build a Business, Not Just a Career

Are you ready to take control of your income, your schedule, and your future? We're looking for driven, coachable, people-first individuals to join our team of life insurance and annuity sales professionals. Whether you're a seasoned agent looking for better support and higher commissions, or you're brand new to the industry and ready to learn a skill that pays for life — this is your opportunity.

This isn't a job. It's a launchpad.

What You'll Do
  • Connect with clients to understand their financial goals and family protection needs
  • Present and recommend life insurance and annuity solutions tailored to each client
  • Guide clients through the application and enrollment process with honesty and care
  • Build long-term relationships that lead to referrals and repeat business
  • Manage your own schedule and pipeline — you're the CEO of your business
  • Continuously grow your skills through ongoing training and mentorship
What We're Looking For
  • Strong communicators who genuinely enjoy helping people
  • Self-starters who are motivated by unlimited earning potential
  • A positive, resilient, growth-oriented mindset
  • Comfort with (or willingness to learn) virtual/phone-based sales
  • Life & health insurance license required — no license yet? No problem. We'll guide you through how to get one
  • Prior sales, insurance, or financial services experience is a plus but NOT required
Why You'll Love This Opportunity

? Unlimited Income Potential Your paycheck isn't capped by a manager's budget — it's driven by your effort. Top performers can earn six figures and beyond.

? 100% Remote Freedom Work from home, from the road, or from anywhere with an internet connection. Design a career around your life, not the other way around.

? No Ceiling, No Limits Full commission structure means every sale is a direct reflection of your hard work — with real, uncapped growth potential as you scale.

? Real Mentorship & Training Whether you're licensed and experienced or brand new to the industry, you'll get the training, scripts, tools, and support to succeed.

❤️ Meaningful Work Help families protect what matters most — financial security, peace of mind, and generational wealth — while building your own.

⏰ True Flexibility Set your own hours. Build your business around your family, your goals, and your lifestyle.

Who Thrives Here
  • Career changers looking for unlimited income potential
  • Stay-at-home parents wanting flexible, high-earning remote work
  • Retirees or veterans seeking a meaningful second career
  • Experienced agents looking for better commissions and more freedom
  • Entrepreneurs at heart who are ready to build something of their own
Ready to Take Control of Your Future?

If you're coachable, hungry for success, and ready to help others while building real wealth for yourself, we want to hear from you. Watch the video above, then apply today and start building the career — and life — you deserve.

? Don't forget: watch "Let's Get to Work" before you apply — it'll show you exactly what you're stepping into.

Note: Since this role is 100% commission, actual earnings vary based on effort, market conditions, and individual performance.