Flexible Work Arrangements Jobs in Chicago, IL

74,517 open positions · Updated daily

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

Painter/Taper

Company: Pepper Construction

Location: Chicago, IL

Posted Jun 30, 2025

Finishing corners and angles, measuring, cutting and installing metal corner beads, filling joints, nail indentations, holes and cracks.

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

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 for flexible work arrangement roles?
Junior remote developers earn $70k–$95k, mid‑level professionals earn $95k–$140k, and senior specialists or leads earn $140k–$200k. Remote‑specific allowances can add 5–10% on top of base pay for high‑cost‑of‑living locations.
What skills and certifications are required for flexible work roles?
Core technical skills include Git, Docker, Kubernetes, and proficiency in at least one cloud platform (AWS, Azure, GCP). Remote collaboration skills involve Slack, Zoom, Notion, and Asana. Certifications such as Certified Remote Work Manager, AWS Certified Solutions Architect, Azure Fundamentals, Google Cloud Professional, PMP, or CSM are highly valued.
How widely available are remote work opportunities in this category?
All 2964 positions support remote work, offering full‑time, part‑time, and contract options. Companies provide VPN, zero‑trust security, and remote onboarding tools, enabling employees to start from any location with a reliable internet connection.
What career progression paths exist for professionals in flexible work arrangements?
Typical paths move from Junior Remote Engineer → Senior Remote Engineer → Remote Technical Lead → Remote Engineering Manager or Remote Product Lead. Parallel tracks include Remote UX Lead, Remote Data Lead, or Remote Customer Success Manager, with opportunities to transition into remote operations or CTO roles.
What industry trends are shaping flexible work arrangements?
The remote‑first trend is accelerating, with 60% of tech firms adopting hybrid models by 2025. Adoption of AI‑driven collaboration tools, real‑time code review, and remote cybersecurity protocols is increasing. Companies increasingly offer remote benefits such as home‑office stipends and global health plans, driving higher demand for qualified remote professionals.

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