Flexible Schedule Jobs in Chicago, IL

34,503 open positions · Updated daily

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

Enterprise Product Risk Lifecycle Analyst

Company: paypal

Location: Chicago, IL

Posted Jul 30, 2025

We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account…

Cloud Data Platform Engineer

Company: DRW

Location: Chicago, IL

Posted Jul 30, 2025

In this hybrid architecture-and-engineering role, you'll help design and build scalable, secure, and high-performance data platforms that enable teams across…

Licensed Customer Service Representative- Insurance Agency

Company: Allstate Insurance - Jackson and Associate Agency

Location: Chicago, IL

Posted Jul 30, 2025

Utilize agency tools and technology to track customer interactions and follow-ups. *Hands-On Training & Licensing Support* (if not already licensed).

Owner Operator Truck Driver

Company: HTA Transpotation INC

Location: Chicago, IL

Posted Jul 30, 2025

Proven experience (2 years) in commercial driving with a valid driver's license (CDL required). As an Owner Operator, you will have the flexibility to manage…

Armed Driver Guard

Company: Loomis Armored US, LLC

Location: Chicago, IL

Posted Jul 30, 2025

With a network of nearly 200 branches, Loomis armored transportation, cash management centers, and cash inventory vaults keep cash flowing throughout financial…

Department Manager - Plumbing

Company: American Vintage Home

Location: Chicago, IL

Posted Jul 30, 2025

Assist sales staff with design, layout, equipment, and material selections when needed. Identify technical weaknesses in trainees and provide support and…

Powder Coat Painter

Company: PROMAN

Location: Chicago, IL

Posted Jul 30, 2025

Proficient in using various power tools related to the painting trade. Operate power tools and machinery safely and effectively during the painting process.

Fine Jewelry Sales and Project Management

Company: Christopher Duquet Fine Jewelry Design

Location: Evanston, IL

Posted Jul 30, 2025

Knowledge of social media platforms and digital marketing strategies. Work in a boutique environment where you can make a real impact on client relationships…

Customer Service Representative - Full-Time

Company: United Airlines

Location: Chicago, IL

Posted Jul 30, 2025

You will be interacting with our domestic and international customers in our lobbies and at gates, helping them with ticketing, baggage, greeting customers as…

Service Technician Trainee Roofing

Company: Complete Bldg Maint Co

Location: Lombard, IL

Posted Jul 30, 2025

This entry-level position is ideal for individuals looking to develop their skills in the commercial roofing repair, and maintenance field.

Overnight Customer Service Representative

Company: Midwest Foods

Location: Chicago, IL

Posted Jul 30, 2025

Manage high volume of phone calls. Experience in data entry and navigating databases. Able to handle finishing bills for 40 routes (600 invoices) in a timely…

Recruiting Manager (Robert Half Marketing & Creative)

Company: Robert Half

Location: Chicago, IL

Posted Jul 30, 2025

As a Recruiting Manager, your responsibilities will include developing and growing a client base and new business opportunities, introducing our services via…

Frequently Asked Questions

What are typical salary ranges for Flexible Schedule roles by seniority?
Entry‑level positions pay $60k–$80k annually. Mid‑level engineers and data scientists earn $80k–$120k. Senior roles, including lead architects and senior product managers, range $120k–$180k, while executive‑level talent can command $180k–$250k with bonuses and equity.
What skills and certifications are required for a Flexible Schedule tech career?
Remote collaboration tools (Zoom, Slack) and version control (Git) are essentials. Technical stacks vary: developers need proficiency in JavaScript/TypeScript, Python, or Go; DevOps engineers should master AWS, Terraform, and Kubernetes; data scientists must be fluent in Python, R, SQL, and machine‑learning libraries. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster, or Google Cloud Professional Data Engineer boost credibility.
Is remote work a standard option for Flexible Schedule listings?
Yes—most Flexible Schedule roles are fully remote or offer a hybrid model. Companies provide cloud‑based development environments, VPN access, and asynchronous communication protocols, allowing you to work from any location while staying connected to distributed teams.
What career progression paths exist within Flexible Schedule roles?
Start as a junior engineer or analyst, then advance to senior, team lead, or principal engineer. Product managers move from associate to senior PM, then to director or VP of Product. Technical architects can transition to solutions architect or head of engineering, often with increased ownership of strategy and mentoring.
What industry trends are shaping Flexible Schedule job opportunities?
Hybrid work models are becoming standard, driven by AI‑powered scheduling tools that manage availability across time zones. Remote‑first startups and Fortune 500 firms alike offer flexible hours to attract global talent, boosting demand for digital nomads and professionals seeking work‑life balance.

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