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.

Chef Manager

Company: Canteen Dining Compass Group USA

Location: Wood Dale, IL

Posted May 14, 2025

Opportunities for professional growth and creative input in menu design and kitchen operations. Leverage digital tools to manage recipes, ordering systems, and…

$40+/Hour-Off-Duty/Retired Law Enforcement Security-Chicago Metro

Company: P4 Security Solutions

Location: Chicago, IL

Posted May 13, 2025

Customer service and front desk reception. Deliver professional and courteous customer service to residents, tenants, employees, students, and guests.

CDL- A Intermodal Truck Driver - Owner Operator - Home Daily

Company: Forward Intermodal

Location: Chicago, IL

Posted May 15, 2025

12 months of verifiable tractor trailer experience. Forward is partnering with Class A CDL Owner Operators in your area to run local/regional intermodal routes…

CDL- A Intermodal Truck Driver - Company Driver - Home Daily

Company: Forward Intermodal

Location: Chicago, IL

Posted May 13, 2025

12 months of verifiable tractor trailer experience. Forward is hiring Class A CDL Company Drivers in your area to run local/regional intermodal routes between…

Pastry Chef - The Ritz-Carlton, Chicago

Company: Sage Hospitality

Location: Chicago, IL

Posted May 15, 2025

Schedule and manage the maintenance/sanitation of the kitchen, equipment and related areas to ensure a healthy, safe work environment which meets/exceeds…

Archive Data Analyst

Company: Rush University Medical Center

Location: Chicago, IL

Posted May 14, 2025

The analyst will be involved in all project activities including archive intake, technical execution, operational workflow review, and validation testing to…

Project Manager - Education Construction

Company: Michael Page

Location: Chicago, IL

Posted May 15, 2025

Train and develop the project team. Our client is a design/build developer who specialize in K-12 and healthcare projects including but not limited to…

Risk Analytics Data Scientist

Company: PayPal

Location: Chicago, IL

Posted May 15, 2025

A master’s or advanced degree in a quantitative field such as statistics, mathematics, finance, or economics. We enable consumers to exchange funds more safely…

Mortgage Wholesale Area / Regional Manager

Company: Lendsure Mortgage- Wholesale Non -QM

Location: Chicago, IL

Posted May 14, 2025

Your duties shall be to solicit and obtain, on a wholesale basis, residential mortgage loan submissions which conform to LendSure’s loan programs, underwriting…

Project Manager

Company: Michael Page

Location: Chicago, IL

Posted May 14, 2025

Bachelors degree in Construction Management or a related field is preferred. Train and develop the Project team and schedule project resources.

Part Time Sales Associate - BOSS Store, Chicago

Company: Hugo Boss

Location: Chicago, IL

Posted May 15, 2025

Utilize effective communication skills in delivering exceptional service to customers, driving business with the merchant group and general problem solving.

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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