Work From Home Jobs in Chicago: High-Paying Roles to Apply For

The rise of remote work has transformed the job market, offering professionals in Chicago the opportunity to secure high-paying roles without the daily commute. With its vibrant economy and diverse industries, Chicago is a hub for remote job opportunities that combine flexibility with competitive salaries. Whether you’re a seasoned professional or looking to transition into a new career, this guide explores high-paying work-from-home jobs in Chicago, key industries, and actionable tips to land your dream role in 2025.

Why Work From Home in Chicago?

Chicago, known as the “Windy City,” is a major economic center with a thriving job market in technology, finance, healthcare, and more. The city’s high cost of living, particularly in areas like downtown, makes high-paying remote jobs especially appealing. Here’s why remote work is a game-changer for Chicago residents:

• Eliminate Commutes: Avoid Chicago’s notorious traffic and save time and money.
• Cost Savings: Reduce expenses on transportation, work attire, and dining out.
• Work-Life Balance: Flexible schedules allow you to balance personal and professional commitments.
• Access to Global Opportunities: Remote work opens doors to companies beyond Chicago, increasing your earning potential.

According to recent data, Chicago’s remote job market has grown significantly, with over 8,500 remote positions listed in 2025 across various platforms. This guide highlights high-paying roles and provides practical advice for securing them.

Top High-Paying Work-From-Home Jobs in Chicago

Below are some of the most lucrative remote job roles available in Chicago, based on current market trends and salary data. These roles span industries like technology, finance, healthcare, and creative fields, offering flexibility and strong earning potential.

1. Software Engineer

Software engineering remains a cornerstone of Chicago’s tech scene. Companies like Toast, Inc. and other Chicago-based startups are actively hiring remote software engineers.

• Average Salary: $100,000–$150,000/year
• Key Responsibilities:
  • Develop and maintain web and mobile applications.
  • Collaborate with cross-functional teams using tools like Zoom and Slack.
  • Write clean, scalable code in languages like Python, Java, or JavaScript.
• Skills Required: Proficiency in coding, problem-solving, and familiarity with Agile methodologies.
• Where to Find Jobs: Platforms like Built In Chicago, FlexJobs, and LinkedIn.

2. Data Scientist

Data science is in high demand, with Chicago’s tech and finance sectors driving the need for skilled professionals. Remote data scientists analyze complex datasets to provide actionable insights.

• Average Salary: $110,000–$160,000/year
• Key Responsibilities:
  • Build and deploy machine learning models.
  • Analyze data to support business decisions.
  • Collaborate with global teams to enhance data pipelines.
• Skills Required: Expertise in Python, R, SQL, and data visualization tools like Tableau.
• Where to Find Jobs: FlexJobs, Indeed, and company career pages like Tempus.

3. Digital Marketing Manager

Chicago’s marketing industry offers robust opportunities for remote digital marketing managers who develop strategies to boost brand visibility and engagement.

• Average Salary: $90,000–$130,000/year
• Key Responsibilities:
  • Manage SEO, PPC, and social media campaigns.
  • Analyze campaign performance using tools like Google Analytics.
  • Develop content strategies to drive traffic and conversions.
• Skills Required: SEO expertise, content creation, and proficiency in marketing platforms.
• Where to Find Jobs: LinkedIn, SimplyHired, and FlexJobs.

4. Financial Analyst

Chicago’s financial sector, a key economic driver, offers high-paying remote roles for financial analysts who provide insights for investment and business decisions.

• Average Salary: $80,000–$120,000/year
• Key Responsibilities:
  • Analyze financial data and market trends.
  • Prepare reports and forecasts for stakeholders.
  • Support budgeting and strategic planning.
• Skills Required: Proficiency in Excel, financial modeling, and knowledge of CRM software.
• Where to Find Jobs: ZipRecruiter, Indeed, and company websites like Enova International.

5. Licensed Therapist (LMFT, LCSW, LCPC)

Remote mental health services are booming, with companies like Rula hiring licensed therapists in Chicago to provide virtual counseling.

• Average Salary: $70–$80/hour per session
• Key Responsibilities:
  • Conduct virtual therapy sessions for individuals and families.
  • Maintain client records and ensure HIPAA compliance.
  • Collaborate with healthcare networks for client referrals.
• Skills Required: Valid licensure (LMFT, LCSW, LCPC), strong communication, and empathy.
• Where to Find Jobs: Rula, BetterHelp, and LinkedIn.

6. AI Engineering Fellow

Chicago’s tech scene is embracing AI, with roles like AI Engineering Fellow at Chicago Public Media offering high pay for innovative projects.

• Average Salary: $120,000–$180,000/year
• Key Responsibilities:
  • Develop AI-driven tools for content accessibility.
  • Build recommendation systems and optimize chatbots.
  • Mentor teams on AI implementation.
• Skills Required: Expertise in machine learning, Python, and cloud computing.
• Where to Find Jobs: Built In Chicago, FlexJobs, and company career pages.

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7. Project Manager

Project managers in Chicago oversee remote teams, ensuring projects are delivered on time and within budget, particularly in tech and finance.

• Average Salary: $95,000–$140,000/year
• Key Responsibilities:
  • Plan and execute projects using tools like Asana or Trello.
  • Coordinate with stakeholders and manage resources.
  • Monitor project progress and mitigate risks.
• Skills Required: PMP certification (preferred), leadership, and time management.
• Where to Find Jobs: LinkedIn, Indeed, and FlexJobs.

8. Underwriter

Underwriters in Chicago’s finance and insurance sectors evaluate risks for mortgage and insurance applications, often working remotely.

• Average Salary: $70,000–$100,000/year
• Key Responsibilities:
  • Analyze credit and financial data.
  • Approve or deny loan and insurance applications.
  • Ensure compliance with regulations.
• Skills Required: Attention to detail, analytical skills, and knowledge of underwriting software.
• Where to Find Jobs: ZipRecruiter, Indeed, and company websites.

9. Content Writer/Editor

Remote content writing and editing roles are ideal for creative professionals in Chicago, with opportunities in tech, marketing, and media.

• Average Salary: $60,000–$100,000/year
• Key Responsibilities:
  • Create blog posts, articles, and marketing content.
  • Edit content for grammar, clarity, and SEO optimization.
  • Collaborate with marketing teams to align content with brand goals.
• Skills Required: Strong writing skills, SEO knowledge, and proficiency in CMS platforms.
• Where to Find Jobs: FlexJobs, Upwork, and LinkedIn.

10. Customer Success Manager

Customer success managers in Chicago ensure client satisfaction and retention, often working remotely for tech and SaaS companies.

• Average Salary: $85,000–$120,000/year
• Key Responsibilities:
  • Onboard and support clients via phone, email, or chat.
  • Analyze customer feedback to improve services.
  • Collaborate with sales and product teams.
• Skills Required: Communication, problem-solving, and CRM proficiency.
• Where to Find Jobs: Built In Chicago, Indeed, and company career pages.

Industries Driving Remote Work in Chicago

Chicago’s diverse economy supports remote work across several high-growth industries. Here are the key sectors offering high-paying remote jobs:

• Technology: Chicago’s tech hub, with companies like Tempus and Toast, Inc., drives demand for software engineers, data scientists, and AI specialists.
• Finance: Home to major firms like Enova International, Chicago offers remote roles in financial analysis, underwriting, and insurance.
• Healthcare: Telehealth and behavioral health services, such as those offered by Rula, create opportunities for licensed therapists and medical coders.
• Marketing: Digital marketing and content creation roles are prevalent, with companies seeking SEO experts and social media managers.
• Education: Remote tutoring and online course development are growing, with platforms like Varsity Tutors hiring in Chicago.

Tips for Landing High-Paying Remote Jobs in Chicago

Securing a high-paying remote job requires strategy and preparation. Here are actionable tips to stand out in Chicago’s competitive job market:

1. Tailor Your Resume and Cover Letter:
   • Highlight transferable skills and remote work experience.
   • Use keywords from job descriptions to pass applicant tracking systems (ATS).
   • Emphasize achievements with quantifiable results (e.g., “Increased website traffic by 30% through SEO strategies”).
2. Build a Strong Online Presence:
   • Optimize your LinkedIn profile with relevant skills and endorsements.
   • Showcase your portfolio on platforms like GitHub (for tech roles) or Behance (for creative roles).
   • Engage in industry discussions on LinkedIn or Reddit’s r/chicago.
3. Upskill and Certify:
   • Pursue certifications like PMP (project management), AWS (cloud computing), or Google Analytics (marketing).
   • Take online courses on platforms like Coursera or Udemy to stay competitive.
4. Network Strategically:
   • Attend virtual industry events or Chicago-based job fairs.
   • Connect with recruiters on LinkedIn who specialize in remote roles.
   • Join local professional groups like the Chicago Workforce Investment Council.
5. Use Reputable Job Platforms:
   • FlexJobs: Offers vetted remote job listings across industries.
   • Built In Chicago: Focuses on tech and startup roles.
   • Indeed and LinkedIn: Provide a wide range of remote job postings in Chicago.
6. Prepare for Remote Interviews:
   • Test your technology (camera, microphone, and internet) before virtual interviews.
   • Demonstrate familiarity with remote tools like Zoom, Slack, and Trello.
   • Highlight your ability to work independently and manage time effectively.
7. Avoid Scams:
   • Be cautious of jobs requiring upfront fees or lacking clear contracts.
   • Verify employers through platforms like FlexJobs, which screens for legitimate opportunities.

Also Read:  Work From Home Jobs in New York City: Top Opportunities for 2025

Challenges of Remote Work and How to Overcome Them

While remote work offers flexibility, it comes with challenges. Here’s how to address common obstacles:

• Isolation: Combat loneliness by joining virtual coworking spaces or local Chicago meetups for remote workers.
• Distractions: Create a dedicated workspace at home and set boundaries with family or roommates.
• Time Management: Use tools like Notion or Asana to prioritize tasks and maintain productivity.
• Career Growth: Seek roles with clear advancement paths and request regular feedback from managers.

Conclusion – Work From Home Jobs in Chicago

Chicago’s remote job market in 2025 offers a wealth of high-paying opportunities across diverse industries like technology, finance, healthcare, and marketing. By leveraging your skills, tailoring your applications, and using reputable job platforms like FlexJobs and Built In Chicago, you can secure a role that aligns with your career goals and lifestyle. Whether you’re a software engineer, data scientist, or licensed therapist, the Windy City’s remote work landscape is ripe with potential. Start your job search today, and take the first step toward a rewarding work-from-home career.

FAQs – Work From Home Jobs in Chicago

1. What are the highest-paying Work From Home Jobs in Chicago?
   
   High-paying remote jobs in Chicago include software engineer ($100,000–$150,000), data scientist ($110,000–$160,000), and AI engineering fellow ($120,000–$180,000).

2. Do I need a degree for high-paying remote jobs in Chicago?
   
   Many roles, like virtual assistants and customer success managers, don’t require a degree. However, tech and finance roles may prefer candidates with degrees or certifications.

3. Where can I find legitimate remote jobs in Chicago?
   
   Use trusted platforms like FlexJobs, Built In Chicago, LinkedIn, and Indeed. Always verify employers to avoid scams.

4. What industries offer the most remote jobs in Chicago?
   
   Technology, finance, healthcare, marketing, and education are the top industries for remote work in Chicago.

5. How can I stand out in Chicago’s remote job market?
   
   Tailor your resume, build a strong LinkedIn profile, pursue relevant certifications, and network with recruiters and industry professionals.

6. Are there part-time remote jobs in Chicago?
   
   Yes, part-time roles like virtual assistants, tutors, and content writers are widely available. FlexJobs lists many part-time remote opportunities.

7. What skills are most in-demand for remote jobs in Chicago?
   
   In-demand skills include coding (Python, Java), data analysis, SEO, project management, and virtual communication.

8. How can I avoid remote job scams?
   
   Avoid jobs requiring upfront fees or lacking clear contracts. Use vetted platforms like FlexJobs and research employers thoroughly.

9. Can I work remotely for a Chicago-based company from outside Illinois?
   
   Many companies hire remote workers regardless of location, but some roles may require Illinois residency. Check job descriptions for details.

10. What tools do I need for remote work in Chicago?
    
    Common tools include Zoom, Slack, Trello, Asana, and industry-specific software like Tableau for data roles or CMS platforms for marketing.