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.

CDL A Tanker Driver - Up to $1800 / wk

Company: Bulk Transport Company Inc

Location: Chicago, IL

Posted Jul 01, 2025

Bulk Transport Company is hiring experienced CDL-A tanker truck drivers to drive regional routes for our liquid division. $1,500 driver referral bonus.

Showroom Sales Consultant

Company: Lightology LLC

Location: Chicago, IL

Posted Jul 01, 2025

Successful project completion track record, understanding of the design and/or specification process with the ability to demonstrate written, verbal, and design…

Retail Sales Consultant, MWT| AT&T Authorized Retailer -Hillside, IL

Company: Millennium Wireless Technology

Location: Hillside, IL

Posted Jun 30, 2025

_*Our stores have thousands of local residents coming in to check on their services, upgrade their cell phones, choose different packages, buy the latest new…

Sr. Graphic Designer, Interior Branding

Company: Stratus

Location: Elmhurst, IL

Posted Jul 01, 2025

Participate in design reviews and contribute creative and technical insights. Graphic design experience, ideally in signage, large-format print, or…

Experienced OTR Pneumatic Truck Drivers

Company: Brady Trucking, Inc.

Location: Chicago, IL

Posted Jul 01, 2025

1 year tractor trailer experience. OTR Class A CDL-A Truck Drivers - $3000 Sign-On Bonus! Brady Trucking is hiring Experienced Pneumatic Tanker Over the Road…

Regional Marketing Specialist

Company: Polsinelli PC

Location: Chicago, IL

Posted Jun 30, 2025

Experience managing budgets and driving cost-effective strategies. The successful candidate will work with the Senior Regional Marketing Manager and on the…

Public Safety Officer II - Armed (Full Time, 3rd Shift)

Company: Advocate Aurora Health

Location: Park Ridge, IL

Posted Jul 01, 2025

A valid driver’s license issued by the Division of Motor Vehicle. Responds to service calls, such as combative or threatening patients or visitors and team…

Lease Purchase Truck Driver

Company: Risinger Brothers Transfer, Inc.

Location: Chicago, IL

Posted Jul 01, 2025

If you pride yourself in being a professional & safe Class-A Truck Driver, you can lease purchase well maintained 2020-2025 Volvo trucks for no money down and…

Temporary Junior Production Designer

Company: HUB International

Location: Chicago, IL

Posted Jul 01, 2025

Manage client assets and develop, organize and maintain client folders within a shared network. Confidently make design updates in Adobe InDesign files, keeping…

Experienced OTR Pneumatic Truck Drivers

Company: Brady Trucking, Inc.

Location: Chicago, IL

Posted Jul 01, 2025

1 year tractor trailer experience. OTR Class A CDL-A Truck Drivers - $3000 Sign-On Bonus! Brady Trucking is hiring Experienced Pneumatic Tanker Over the Road…

1st Shift Machine Operator

Company: Champion Packaging & Distribution Inc.

Location: Woodridge, IL

Posted Jun 30, 2025

Operator will be required to perform the mechanical and GMP duties. Relevant experience as a Machine Operator – Basic mechanical skills & aptitude.

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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