ZipRecruiter

Log In

1

Weekend Contractor Jobs in Chicago, IL (NOW HIRING)

Fabric Health

Outreach Associate (Contractor)

Chicago, IL · On-site

$20 - $22/hr

Weekend availability is required! 🚨 Outreach Associate (Contractor) Location: Chicago Compensation: $20-$22 hourly Type: 1099 Independent Contractor About Fabric Health Founded in 2021, Fabric ...

previous pagenext page

Showing results 21-40

All JobsContractor JobsWeekend Contractor JobsWeekend Contractor Jobs in Chicago, IL

Weekend Contractor information

See Chicago, IL salary details

$83.4K

$144.3K

$258.1K

How much do weekend contractor jobs pay per year?

As of Aug 17, 2026, the average yearly pay for weekend contractor in Chicago, IL is $144,321.00, according to ZipRecruiter salary data. Most workers in this role earn between $101,000.00 and $175,600.00 per year, depending on experience, location, and employer.

Do weekend contractors work on the weekend?

Weekend contractors typically work on weekends, as their schedule is often designed to accommodate projects or tasks during those days. Their work hours depend on the specific job requirements and client needs, but weekend work is common for this role.

What is the difference between Weekend Contractor vs Part-Time Handyman?

AspectWeekend ContractorPart-Time Handyman
CredentialsMay require specialized licenses or certifications depending on the workUsually no formal certifications required, basic skills often sufficient
Work EnvironmentTypically works on specific projects, often on client sites or homesPerforms repairs and maintenance tasks, often in residential settings
Employer & Industry UsageHired by clients or companies for short-term projects, common in construction and renovationHired directly by homeowners or property managers for ongoing or one-off repairs

Weekend Contractors and Part-Time Handymen both work on a flexible schedule, but Weekend Contractors often handle specialized projects requiring certifications, while Part-Time Handymen focus on general repairs without formal credentials. The choice depends on the complexity of work and required expertise.

What are the key skills and qualifications needed to thrive as a weekend contractor?

To excel as a Weekend Contractor, you typically need relevant trade skills or professional expertise, such as carpentry, electrical, or general handyman abilities, often supported by certifications or licenses as required by the field. Familiarity with essential tools, safety protocols, and scheduling or project management systems is necessary for efficient work. Strong time management, reliability, and customer service skills help you stand out when working independently or with clients on tight deadlines. These abilities are crucial for delivering quality results, maintaining safety standards, and building a trustworthy reputation for short-term or project-based work.

What is a weekend contractor?

Weekend contractors are professionals who perform contract-based work specifically during weekends, often to accommodate project deadlines, business needs, or their personal schedules. They may work in a variety of industries such as construction, IT, event management, or hospitality. This arrangement allows businesses to maintain productivity outside of standard weekday hours while offering flexibility for workers who cannot commit to a traditional workweek. Weekend contractors are typically hired for specific projects or tasks and may be paid hourly, per project, or on a retainer basis.

What are the typical expectations and challenges for a weekend contractor in managing work-life balance?

Weekend Contractors are often expected to handle assignments during non-traditional hours, which can be ideal for those seeking flexible schedules or supplemental income. However, balancing personal commitments and rest with project deadlines can be a challenge, especially if weekend workloads fluctuate or urgent tasks arise. Clear communication with clients or supervisors about availability and setting boundaries is essential to maintain a healthy work-life balance. Collaborating with teams remotely or on-site may also require flexibility and proactive time management to ensure successful project delivery.

What are the most commonly searched types of Contractor jobs in Chicago, IL?

The most popular types of Contractor jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Weekend Contractor jobs?

Cities near Chicago, IL with the most Weekend Contractor job openings:

Weekend Contractor jobs near you
Infographic showing various Weekend Contractor job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 70% Full Time, 24% Part Time, 4% Contract, and 1% Nights. Highlights an 94% Physical, 2% Hybrid, and 4% Remote job distribution, with an average salary of $144,321 per year, or $69.4 per hour.

Commercial Roofing Services - Independent Contractor Companies

City Wide Facility Solutions

Joliet, IL

Full-time

Re-posted 3 days ago

Job description

Description

City Wide Facility Solutions is the largest management company in the building maintenance industry. We secure and manage commercial contracts and partner with skilled independent contractors to perform the work. We handle the sales, client communication, billing, and collections - so you can focus on doing what you do best.

We are selectively partnering with established Independent Contractors and service companies to service our commercial clients in the region. If you operate a structured business, deliver professional facility maintenance, restoration, or renovation services, and are looking for steady, recurring work - without the burden of chasing new contracts or managing collections - this may be a strong fit.

City Wide helps you grow your revenue, keep your crews busy, and get paid consistently - including guaranteed payment on the 10th for work performed.

We operate throughout South Chicagoland and Northwest Indiana - a strong commercial market with warehouses, medical facilities, manufacturing sites, schools, and municipal buildings.

For more information, contact Sandra Rivas at 708-365-8535 or chicagoshores-ic@gocitywide.com.

Requirements

We are selectively partnering with contractors who meet the following:

  • Proven experience in commercial roofing (required)
  • Proper licensing for commercial roofing work (as applicable)
  • General liability insurance and workers' compensation coverage
  • Ability to assess, quote, and execute projects independently
  • Professional-grade equipment and crew
  • Strong communication and reliability
  • Commitment to safety, quality, and timelines

Preferred:

  • Experience working in occupied commercial or medical environments
  • Ability to provide clear documentation (photos, reports, scope clarity)
The Opportunity

ity Wide Facility Solutions is seeking a qualified commercial roofing contractor to support a current client project within our portfolio.

This is a project-based opportunity with the potential for ongoing work across multiple commercial properties, depending on performance, professionalism, and execution quality.

We manage a large base of commercial clients across office, medical, industrial, and institutional facilities. Our model is built around bringing vetted service providers into well-scoped, professionally managed opportunities-allowing contractors to focus on execution, not sales.

If you are looking to supplement your pipeline with well-defined commercial work and long-term partnership potential, this may be a strong fit.

If this is your company, keep reading.

INDEPENDENT CONTRACTORS MUST PROVIDE THE FOLLOWING:

  • Valid Business License (if necessary for the service type)
  • Worker's Compensation Insurance
  • General Liability Insurance
  • Federal EIN #
  • Other verifiable business
  • 18 years of age minimum
  • Favorable background investigation results
  • You can not be a sole proprietor

The selected contractor will be responsible for delivering high-quality commercial roofing services, which may include:

  • Roof inspections and condition assessments
  • Leak detection and repair
  • Preventative maintenance
  • Partial or full roof replacement (as applicable)
  • Flat roof systems (TPO, EPDM, modified bitumen, etc.)
  • Proper documentation, reporting, and photo verification

Work will be performed in active commercial environments, requiring professionalism, coordination, and adherence to safety standards.

City Wide will:

  • Coordinate with the client
  • Define scope and expectations
  • Manage communication and administrative flow

You focus on:
Executing the work at a high level

Benefits

We help you grow a real business - not just pick up extra work.

  • Consistent, Recurring Contracts (No Hunting Required)
    We bring you qualified commercial accounts so you can focus on operations - not cold calling, bidding, or chasing leads.
  • Reliable, On-Time Payments
    Eliminate collections headaches. We handle billing and client payment - you get paid consistently and predictably.
  • Scale Your Revenue Quickly
    Access multiple accounts across our territory - grow from a small crew to a multi-team operation with steady work.
  • Professional Account Management Support
    Our Facility Solutions Managers handle client communication, inspections, and issue resolution - helping you retain accounts and maintain high standards.
  • No Sales, No Admin Burden
    We manage contracts, client expectations, and service coordination - freeing you to focus on delivering quality work and building your team.
  • 20+ Other Opportunities
    Expand into additional services (floor care, porter services, consumables, specialty cleaning) and increase revenue per account.
  • Long-Term Partnership Model
    We are invested in your growth - many of our partners have scaled into six-figure and multi-crew businesses with us.

Apply