Contract Jobs in Chicago, IL

5,894 open positions · Updated daily

Looking for Contract jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Contract position in the Chicago, IL area.

Management & Sales Training Program

Company:

Location: Ottawa, IL

Posted Jan 23, 2025

Field Sales Representative - $60k - $200k Compensation

Company:

Location: St. Charles, IL

Posted Jan 23, 2025

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in West Chicagoland. These representatives will educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. The company stands out due to its fully staffed departments, allowing reps more time for sales. Compensation includes a draw against commission, commission on approved sales, a vehicle allowance, quarterly bonuses, full insurance benefits, a 401K with employer match, and a training & development program. Responsibilities involve prospecting, qualifying, and closing sales, managing territories, inspecting properties for damage, and building customer relationships. Qualifications include 2+ years of full-cycle sales experience, a reliable vehicle, excellent communication skills, and CRM experience.

Roofing Sales $65K-200K Total Compensation!

Company:

Location: Romeoville, IL

Posted Jan 23, 2025

Roofing Sales Immediately Hiring

Company:

Location: Oak Park, IL

Posted Jan 23, 2025

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in West Chicagoland. These representatives will educate homeowners about storm damage entitlements for roofing, siding, and gutter projects, offering them protection at reduced costs. The company stands out due to its fully staffed departments, enabling sales reps to focus on sales without administrative burdens. AmeriPro Roofing offers competitive compensation including a draw against commission, commission on approved sales, a vehicle allowance, quarterly bonuses, full insurance benefits, a 401K with employer match, and a training & development program. The role involves prospecting, qualifying, and closing new sales, managing a territory, conducting property inspections, and building customer relationships. Qualifications include 2+ years of full-cycle sales experience, a reliable vehicle, excellent communication skills, and CRM experience.

Roofing Sales $65K-200K Total Compensation!

Company:

Location: Downers Grove, IL

Posted Jan 23, 2025

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in West Chicagoland. These representatives will educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. The company stands out due to its fully staffed departments, allowing sales reps more time for tasks. Compensation includes a draw against commission, commission on approved sales, a vehicle allowance, quarterly bonuses, full insurance benefits, a 401K with a 4% employer match, and a training & development program. Responsibilities involve prospecting, qualifying, and closing new sales, managing territories, inspecting properties for damage, and building customer relationships. Qualifications include 2+ years of full-cycle sales experience, a reliable vehicle, excellent communication skills, and CRM experience.

Management & Sales Training Program (Madison/Rockford)

Company:

Location: Belvidere, IL

Posted Jan 23, 2025

The Sherwin-Williams Management & Sales Training Program is an 18-24 month entry-level position designed to prepare individuals for a Store Management role. The program includes 6-8 weeks of intensive training, followed by a typical 44-hour workweek. Participants will collaborate with store management, oversee a million-dollar business, and learn all aspects of operations, sales, and strategy. The training equips participants with skills for a successful career in management and professional sales, offering limitless career opportunities and leadership development. Sherwin-Williams values diversity and inclusivity, encouraging applications from all backgrounds.

Staff Accountant

Company: Addison Group

Location: Chicago, IL

Posted Jan 23, 2025

Outside Sales Representative

Company:

Location: Villa Park, IL

Posted Jan 23, 2025

Frequently Asked Questions

What are the typical hourly or weekly rates for contract tech roles at different seniority levels?
Entry‑level contractors earn $30–$50 per hour, mid‑level $50–$80, senior‑level $80–$120, specialist roles such as AI/ML or security typically $100–$150, and lead or architect positions can exceed $150 per hour. Regional cost of living and the specific technology stack also influence these ranges.
What skills and certifications are most sought after for contract tech positions?
High‑demand skills include cloud platform expertise (AWS Certified Solutions Architect, Azure Solutions Architect, GCP Professional Cloud Architect), Kubernetes & Helm, Terraform, CI/CD tools like Jenkins or GitLab CI, security certifications such as CISSP or CompTIA Security+, data engineering tools (Snowflake, BigQuery), programming languages (Python, Go, TypeScript), and Agile or Scrum facilitation. Demonstrated project experience on similar stacks is often required.
Can contract tech roles be performed remotely, and what is the typical remote work policy?
Approximately 80–90% of contract tech positions are fully remote, with clients providing VPN access and collaboration tools. Some contracts may require occasional on‑site visits for client meetings or data‑center access, but most clients emphasize a remote‑first workflow and enforce compliance with local data‑residency laws.
How can contractors advance their careers while staying in contract work?
Contractors can build a strong portfolio, specialize in high‑paying stacks, pursue advanced certifications, and secure retainer or multi‑project contracts. Continuous learning keeps rates high, and many contractors transition into permanent roles with the same clients or move into consulting, contract management, or specialized advisory positions.
What current industry trends are influencing the demand for contract tech talent?
Digital transformation, cloud migration, AI/ML adoption, cybersecurity needs, remote‑first culture, microservices architecture, edge computing, and the rise of platform‑as‑a‑service (PaaS) are driving companies to hire contractors for rapid experimentation, scaling, and expertise that is too scarce for full‑time positions.

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