Sales Jobs in Chicago, IL

From ADP's office in the Willis Tower to Cintas territories across the west suburbs, Chicago sales jobs mix Loop desks with Chicagoland driving routes. The guides below cover every sales role in Chicago, who is hiring, what it pays and how to get started.

Inside Sales Representative Jobs Outside Sales Representative Jobs Sales Representative Jobs

Why Sales Work Is Different in Chicago

Chicago is a headquarters town and a freight town at once, and both feed sales hiring. World Business Chicago counts 30 Fortune 500 headquarters in the region, and six of the seven Class I railroads converge here, which helps explain why freight brokers like Echo Global Logistics hire whole classes of client sales reps in River North. Payroll and HR companies sell to the metro's small and mid-size businesses: ADP runs territories out of 233 S. Wacker Drive, and Paylocity is headquartered in Schaumburg.

The other half of the market is on the road. Cintas lists more than 40 Chicago-area sales roles on its own careers site, from Maywood and Romeoville to Schaumburg and Gurnee, Sysco Chicago works restaurant accounts from Des Plaines to Evanston, and Grainger's Imperial Supplies covers the Chicago automotive market. Sales and related work paid a metro mean of $28.84 an hour in the BLS May 2025 survey, and because Illinois requires employers with 15 or more workers to post a pay scale, most Chicago sales listings show base and commission before you apply.

Top Sales Employers in Chicago

These employers had sales openings in the Chicago area on their own careers sites this month:

  • Cintas - uniform, facility services and first aid sales reps across Chicagoland, plus inside sales on the Southwest Side, at $60,000 to $150,000 with commission.
  • ADP - account executives selling payroll and HR services from its Wacker Drive office, at $50,100 to $99,800 base.
  • Echo Global Logistics - client and carrier sales reps at its River North headquarters, starting at $50,000 plus uncapped commission.
  • Grainger - the Lake Forest industrial supplier hires district reps through Imperial Supplies and runs inside sales at headquarters.
  • Sysco - Sysco Chicago hires outside reps for restaurant accounts in Des Plaines, Evanston and Skokie at $47,200 to $78,600.
  • Comcast Business - small-business account executives on W. North Avenue and in Schaumburg, and door-to-door Xfinity reps in the suburbs.
  • Blue Cross and Blue Shield of Illinois - parent HCSC hires marketing service reps who support its group health sales executives, at $63,300 to $114,300.

Sales Career Paths in Chicago

  • Getting started - Sales Representative, Inside Sales Representative, Business Development Representative. Phone-based and entry roles where most Chicago sales careers begin, often hybrid and reachable by the L.
  • Territory and closing roles - Outside Sales Representative, Account Executive. Quota-carrying jobs with a territory or a book of prospects, and most of the commission upside.
  • Keeping and growing accounts - Account Manager, Sales Manager. Roles that manage existing customers or lead a team of reps.
  • Licensed and specialty sales - Insurance Sales Agent, Automotive Sales Consultant. Sales with an industry of its own, including the one that needs a state license.

How to Start a Sales Career in Chicago

  • No state license for general sales - Illinois does not license inside, outside or B2B sales representatives.
  • Illinois insurance producer license - required to sell insurance, issued by the Illinois Department of Insurance after a state exam. HCSC asks its marketing service reps to get life and health licenses within 90 days.
  • Valid driver's license - required by Cintas and Sysco for territory roles, with Sysco setting auto insurance minimums.
  • DePaul University Center for Sales Leadership - Driehaus College of Business, 1 E. Jackson Blvd in the Loop, with a sales leadership concentration and minor.
  • City Colleges of Chicago - Business Apprenticeship associate degree at Harold Washington, Truman, Kennedy-King, Olive-Harvey, Daley and Wright, plus a Management/Marketing certificate.

Only the insurance license and, for driving roles, a driver's license are legal or hard requirements; degrees and certificates are employer preference, and Echo and Cintas both hire without a degree.

Sales Salaries in Chicago

  • Entry - about $46,000 to $60,000 base for inside, business development and entry territory reps, with commission on top.
  • Mid - roughly $60,000 to $120,000 with commission for experienced outside reps and account executives.
  • Senior - $120,000 and up for top producers and technical reps, and a metro median near $158,700 for sales managers.

These are estimates from BLS May 2025 wage data for the Chicago metro and ranges Chicago employers posted this year. Base pay is only part of it: Cintas adds commission, a quarterly bonus and a car allowance, Imperial Supplies guarantees a first-year bonus, and software firms often add equity. Compare the base, the commission plan and the territory together.

Frequently Asked Questions

Do you need a license to work in sales in Illinois?

Not for most sales jobs. Illinois has no license for general, inside or outside sales reps. Selling insurance is the main exception and requires a producer license from the Illinois Department of Insurance.

What sales jobs in Chicago hire with no experience?

Inside and business development roles are the usual entry point. Echo Global Logistics hires client sales reps with zero to two years of experience and trains them for six weeks, and Cintas lists a high school diploma or GED as the minimum for many sales roles.

How much do sales jobs pay in Chicago?

The BLS puts the metro median for wholesale and manufacturing sales reps at about $75,000 a year. Posted Chicago ranges run from $47,200 at Sysco to $150,000 with commission at Cintas, and sales managers earn a metro median near $158,700.

Do I need a car for a sales job in Chicago?

For outside and territory roles, yes, and employers such as Cintas pay a car allowance. Inside sales roles in the Loop and River North are reachable by the L and are often hybrid.

Are Chicago sales jobs commission only?

Most posted Chicago sales jobs pay a base plus commission, not commission only. Illinois pay transparency rules mean employers with 15 or more workers must show the pay scale in the posting, so you can check before applying.

Ready to get started? Browse all current sales job openings in Chicago, IL on LocalJobPage.