Toll Collection Jobs in Chicago, IL (NOW HIRING)

About the Skyway

Built by the City of Chicago in 1958, the Chicago Skyway Toll Bridge (“Skyway”) is a 7.8-mile toll road connecting the Indiana Toll Road to the Dan Ryan Expressway on Chicago’s South Side. A key feature of the Skyway is the half-mile-long steel truss “High Bridge,” which spans the Calumet River and Calumet Harbor—an important route for industrial shipping. The bridge’s main span is 650 feet long and provides 125 feet of vertical clearance.

• Our Vision: To be the best operational toll road project in the United States, recognized for delivering exceptional value to our customers, partners, and community through operational excellence and sustainable long-term performance.
• Our Mission: Our mission is simple: Provide the safest, most time-efficient, convenient, and reliable highway to and through Chicago.

Position Summary

At Skyway Concession Company LLC (SCC), we are guided by our core values: Safety, Ownership, Collaboration, Integrity & Stewardship, and Innovation. We look for team members who demonstrate these values every day. The Toll Collector reports to the Tolling Shift Supervisor and is responsible for safely and efficiently processing vehicles traveling through the Skyway by collecting tolls and assisting customers. This role requires following established procedures, handling cash accurately, and using sound judgment to address unusual situations in the lane. Errors can impact operations, financial accuracy, and customer experience. Work is performed primarily in a toll booth, with exposure to weather, noise, and vehicle fumes. This role requires standing for extended periods, reaching and turning while handling transactions, and occasionally walking between lanes to assist customers or adjust assignments. The position can be fast-paced and stressful during high traffic volumes and requires strong focus and manual dexterity.

Essential Functions (Duties and Responsibilities)

• Provide courteous and professional customer service to motorists
• Collect tolls accurately and provide correct change
• Ensure proper vehicle classification and axle counts
• Open, operate, and close traffic lanes following procedures
• Monitor safety and security conditions and take appropriate action
• Record and report all toll transactions accurately
• Count and reconcile cash drawers at the start and end of each shift
• Deposit cash in designated toll plaza safes
• Complete daily reports and required documentation
• Keep traffic lanes clear and safe when logging in and out of terminals
• Follow procedures for emergencies, oversized vehicles, and unusual situations
• Resolve issues such as unpaid tolls, misclassifications, and payment problems
• Assist customers with credit card transactions and electronic tolling issues
• Provide directions and share current road condition information
• Enter accurate data into lane terminals
• Respond quickly and effectively in emergency situations
• Perform other duties as assigned

Qualifications (Knowledge, Skills, Abilities (KSA), and Competencies)

• High school diploma, GED, or equivalent experience
• 1–2 years of customer service, positive and professional customer-focused attitude, and experience in toll collection and cashiering
• Cash-handling experience and the ability to follow cash-handling procedures accurately
• Familiarity with electronic toll systems (e.g., I-Pass)
• Strong communication and interpersonal skills
• Ability to remain calm and professional under pressure
• Ability to make quick, sound decisions in emergencies
• Knowledge of local roads and directions
• Strong attention to detail in completing reports and forms. Strong communication, teamwork, and problem-solving skills
• Dependable, safety-focused, and detail-oriented
• Experience in conflict resolution and de-escalation

Work Environment and Physical Demands

This position is primarily performed in a toll booth and outdoor environment. Employees must regularly stand, communicate, and use equipment to process transactions.

• May require standing for long periods and walking between lanes
• Occasional lifting up to 25 pounds
• Exposure to weather, traffic noise, and fumes
• Reasonable accommodation may be provided for individuals with disabilities

Risk, Health, Safety, Environment & Quality

All employees are expected to support SCC’s commitment to safety, environmental responsibility, and regulatory compliance. This includes following safety procedures, reporting hazards immediately, and contributing to a safe and secure workplace.