Flexible Work Environment Jobs in Chicago, IL

76,048 open positions · Updated daily

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

View Details Apply on SimplyHired

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…

View Details Apply on SimplyHired

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…

View Details Apply on SimplyHired

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…

View Details Apply on SimplyHired

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…

View Details Apply on SimplyHired

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…

View Details Apply on SimplyHired
private practice full time be or bc

A Private, Long-Standing, & Reputable Practice in Northshore Chicago Suburbs Seeking Dermatologist & Mohs Surgeon

Company: Deerfield Dermatology

Location: Chicago Northshore Suburbs, IL

Posted Jun 30, 2025

View Details Apply on healthecareers.com

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…

View Details Apply on SimplyHired

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…

View Details Apply on SimplyHired

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…

View Details Apply on SimplyHired

Machine Operator

Company: Closets By Design Chicago Downtown

Location: Chicago, IL

Posted Jun 30, 2025

Operate woodworking machinery and hand tools. Experience with woodworking equipment and hand tools is a plus. Paid holidays and paid time off.

View Details Apply on SimplyHired

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.

View Details Apply on SimplyHired

Frequently Asked Questions

What are typical salary ranges by seniority in flexible work roles?
Entry‑level (0‑2 yrs) typically earns $70k–$90k. Mid‑level (3‑5 yrs) ranges $90k–$120k. Senior (6‑10 yrs) $120k–$160k. Staff/Principal engineers $160k–$200k. These ranges include remote allowances and are based on current market data from jobtransparency.com.
What skills and certifications are required for flexible tech positions?
Essential skills include JavaScript (React, Node.js), Python or Go, cloud platforms (AWS Certified Solutions Architect, Azure Developer Associate), CI/CD pipelines (Jenkins, GitHub Actions), containerization (Docker, Kubernetes), and agile frameworks (Scrum, Kanban). Certifications that boost marketability: AWS Certified DevOps Engineer, Certified ScrumMaster, Google Cloud Professional Data Engineer, Microsoft Certified: Azure Data Scientist Associate.
Is remote work available for most flexible roles?
Yes—over 90% of positions are fully remote with optional hybrid options. Core hours typically fall between 10am‑3pm, allowing flexible start/finish times and support for international time zones. Employers often provide stipends for home office equipment and VPN access.
What are common career progression paths in a flexible work environment?
Typical progression: Junior Engineer → Mid‑level Engineer → Senior Engineer → Staff Engineer → Principal Engineer → Engineering Manager → VP of Engineering. Advancement relies on measurable impact on product metrics, mentorship of junior staff, and leadership in cross‑functional initiatives.
What industry trends are shaping flexible work roles?
The flexible segment is growing due to cloud adoption, AI/ML workloads, low‑code platforms, and distributed collaboration tools. Companies are expanding remote talent pools globally, driving up salaries for high‑skill roles and creating demand for continuous learning in emerging technologies like Terraform, Serverless, and DataOps.

Related Pages

All Flexible Work Environment Jobs 4,613 jobs All Jobs in Chicago, IL 404,964 jobs Flexible Work Environment in Remote 2,990,724 jobs Flexible Work Environment in Other US Location 2,601,924 jobs Flexible Work Environment in New York City, NY 691,236 jobs Flexible Work Environment in Multiple Locations 608,700 jobs Flexible Work Environment in USA 545,784 jobs Flexible Work Environment in Washington DC 421,620 jobs Travel in Chicago, IL 79,837 jobs Full Time in Chicago, IL 46,687 jobs Retirement Plan in Chicago, IL 43,124 jobs 401(K) in Chicago, IL 37,542 jobs Health Insurance in Chicago, IL 34,384 jobs Life Insurance in Chicago, IL 33,039 jobs