Sales Representative Jobs in Chicago, IL

Sales Representative Job Market in Chicago, IL (2026)

The Sales Representative job market in Chicago, IL is moderately active, with 105 open positions across 15+ employers. Hiring momentum is strong, with 47 new listings in the past month and 16 in the last week alone.

What Can You Expect to Earn?

The median salary for Sales Representative roles in Chicago, IL is $70,000, with most positions paying between $55,000 and $81,250. Top performers can earn $100,000 or more at the 90th percentile. Note that 54% of listings in this market don't disclose salary, so actual compensation varies — especially for negotiable roles. For higher compensation, consider Tampa, FL where the median is $75,000.

Skills That Employers Want

Analysis of job descriptions in Chicago, IL shows the most requested skills are CRM, Customer Service, Excel, Salesforce, Logistics, and Nursing. Including these keywords in your resume can significantly improve your ATS match rate. Our Sales Representative resume example shows how to integrate these naturally.

Who's Hiring?

The most active employers for Sales Representative positions in Chicago, IL include Stryker, Sales Focus Inc., System One, GIA Legacy Planning, and Aggreko. Use JobsChat AI to filter by specific companies or discover employers that match your preferences.

Remote & Flexible Work

10% of Sales Representative jobs in Chicago, IL offer remote or hybrid work (11 positions). While most positions are on-site, a growing number of employers offer flexible arrangements.

Ready to Apply?

Start with our Sales Representative resume example. Pair it with a tailored cover letter. Then use JobsChat AI to search all 105 positions and generate application materials in minutes. Browse Sales Representative jobs in other cities or explore all jobs in Chicago, IL.