Outside Sales Representative Jobs in Chicago, IL

Outside Sales Representative Job Market in Chicago, IL (2026)

The Outside Sales Representative job market in Chicago, IL is emerging, with 8 open positions across 5+ employers. Hiring momentum is strong, with 3 new listings in the past month and 1 in the last week alone.

What Can You Expect to Earn?

The median salary for Outside Sales Representative roles in Chicago, IL is $100,000, with most positions paying between $93,750 and $105,000. Top performers can earn $114,000 or more at the 90th percentile. Note that 50% of listings in this market don't disclose salary, so actual compensation varies — especially for negotiable roles. For higher compensation, consider Orlando, FL where the median is $225,000.

Skills That Employers Want

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

Who's Hiring?

The most active employers for Outside Sales Representative positions in Chicago, IL include System One, Sales Focus Inc., AmeriPro Roofing, Home Genius Exteriors West, and Nextep. Use JobsChat AI to filter by specific companies or discover employers that match your preferences.

Ready to Apply?

Start with our Outside Sales Representative resume example. Pair it with a tailored cover letter. Then use JobsChat AI to search all 8 positions and generate application materials in minutes. Browse Outside Sales Representative jobs in other cities or explore all jobs in Chicago, IL.