Flexible Work Schedule Jobs in Chicago, IL

75,597 open positions · Updated daily

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

Cloud Infrastructure Architect

Company: Sargent & Lundy

Location: Chicago, IL

Posted Jul 23, 2025

We are seeking a highly experienced and strategic Cloud & Infrastructure Architect to lead the design, governance, and implementation of enterprise-grade cloud…

CDL A Regional Driver - 100% no-touch freight

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 24, 2025

Company drivers earn up to $105,000 per year. G&D Integrated that values our employees and drivers like family. At G&D, you’re in control.

CDL A OTR Driver - get home weekly!

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 24, 2025

Company drivers earn up to $105,000 per year. G&D Integrated that values our employees and drivers like family. At G&D, you’re in control.

Regional CDL A Truck Driver: home at least weekly

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 24, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

Area Marketing Manager, Premium Select Hotels

Company: First Hospitality

Location: Chicago, IL

Posted Jul 23, 2025

Oversee portfolio social media efforts, driving following and engagement, fostering collaboration amongst broader marketing strategies.

Data Analyst - Remote

Company: Guidehealth

Location: Chicago, IL

Posted Jul 23, 2025

Employees provide their own internet connection, capable of conducting video calls on camera and connecting to various internal and external systems.

Software Development Engineer

Company: WEX Inc.

Location: Chicago, IL

Posted Jul 23, 2025

You will be responsible for building and maintaining efficient development pipelines, driving automation, and contributing to scalable deployment strategies.

Regional CDL A Truck Driver

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 24, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

Retail Sales Associate

Company: MY WIRELESS IL, INC

Location: Wood Dale, IL

Posted Jul 23, 2025

Experience prospecting through outbound calls. Training and developing your skills to become a top My Wireless Retail Sales Associate, which leads to…

Analytical Lead Associate, Sales Associate Program (English)

Company: Google

Location: Chicago, IL

Posted Jul 23, 2025

Experience with data analysis using data sets using tools (e.g., SQL, Looker, PowerBI, or other data analysis software) through full-time roles, internships, or…

Second Shift Custodian

Company: Bennett Day School Inc

Location: Chicago, IL

Posted Jul 24, 2025

Bennett Day School is a progressive independent day school looking for passionate educators with an innovative spirit and rich background in learning and school…

Registered Nurse - Burr Ridge Immediate Care

Company: Loyola University Health System

Location: Burr Ridge, IL

Posted Jul 23, 2025

Triage - Handles nurse-directed telephone calls from patients and seeks appropriate input and direction from the physician or functions from signed protocols if…

Frequently Asked Questions

What are typical salary ranges for Flexible Work Schedule roles at different seniority levels?
Entry‑level: $60‑$90k annually. Mid‑level: $90‑$140k. Senior: $140‑$200k. Lead/Director: $200‑$300k. These ranges vary by tech stack, region, and company size but generally reflect market rates for remote work.
What technical skills and certifications are most valuable for Flexible Work Schedule positions?
Key skills: proficiency with asynchronous tools (Slack, Zoom, Microsoft Teams), project management software (Jira, Asana, Trello), version control (Git/GitHub), cloud platforms (AWS, Azure, GCP), and CI/CD pipelines. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster (CSM), or PMP add credibility and open higher‑pay roles.
Are Flexible Work Schedule roles fully remote, or do they require occasional office visits?
Most Flexible Work Schedule listings allow 100% remote work, with optional hybrid or occasional on‑site meetings for team alignment. Employers typically provide a stipend for home‑office setup and stipulate flexible hours to accommodate different time zones.
How can a professional advance their career while working a Flexible Work Schedule?
Start as a junior engineer or analyst, then move to senior roles, team lead, or product owner. Remote experience can lead to global project assignments, mentorship positions, and eventually senior leadership roles such as Remote Program Manager or VP of Engineering with flexible terms.
What current industry trends are impacting Flexible Work Schedule opportunities?
The rise of AI‑driven collaboration tools (Figma’s auto‑layout, GitHub Copilot), increased focus on cybersecurity for remote teams, and the growth of virtual offices are shaping demand. Companies are prioritizing flexible schedules to retain high‑talent talent in a post‑pandemic world.

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