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Bookkeeping Contractor Jobs in Chicago, IL (NOW HIRING)

CTH Recruiting LLC

Bookkeeper

Highland Park, IL

$75K/yr

... bookkeeping experience who is organized, accurate, and comfortable working in a fast-paced environment with multiple projects. The ideal candidate has experience within construction, contracting, or ...

Real Estate Firm

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Senior Real Estate Bookkeeper

Arlington Heights, IL · On-site

$45K - $55K/yr

  • PTO

Proven experience managing tiered billing cycles (Monthly, Quarterly, Annual) for a large roster of independent contractors. * 5+ years bookkeeping exp, Real Estate brokerage preferred. * Excel:

Robert Half

Full Charge Bookkeeper

Chicago, IL · On-site

$60K - $70K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

Sage 100 Contractor Administration * Perform and support all accounting-related functions within ... Bookkeeping experience * Payroll * SAGE is required, Or QuickBooks * Don't need prior management ...

Rise25

Bookkeeper/Accountant

Chicago, IL · Remote

Job Details: We are looking for a great bookkeeper/accountant to help our fast-growing company ... contractors and commission checks to referral partners. This is a remote position so you can work ...

SharpPencil AI

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Sales Representative

Chicago, IL · Remote

$200K/yr

We utilize advanced AI technology to provide third-party bookkeeping, accounting, tax preparation ... This is a purely Commission-Driven, 1099 Independent Contractor position that offers high earning ...

MARS Solutions Group

Operations Clerk

Aurora, IL · On-site

$17 - $20.50/hr

Will be walking between docks in the cold area (35 degrees), so contractors are urged to always ... In some instances, they might take care of light bookkeeping duties or post updates to the company ...

TrueMatch Talent Group

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Senior Accountant

Buffalo Grove, IL · On-site

$80K - $100K/yr

  • Medical

  • Dental

  • Life

  • PTO

This is an excellent opportunity for an experienced Accountant or Senior Bookkeeper looking to ... roofing contractor in South Florida to identify a driven and relationship-focused Commercial ...

Wintrust

Commercial Draw Manager I

Rosemont, IL · On-site

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

... bookkeeping with a general contractor. * Direct experience in commercial construction loan underwriting / funding / disbursement experience is a plus. * Must be highly proficient with MS Excel.

Wintrust

Commercial Draw Manager I

Rosemont, IL · On-site

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

... bookkeeping with a general contractor. * Direct experience in commercial construction loan underwriting / funding / disbursement experience is a plus. * Must be highly proficient with MS Excel.

Boxer Exteriors

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Office Manager

Wheaton, IL · On-site

$65K - $80K/yr

  • PTO

Payroll & contractor compliance: Manage and oversee contractor documentation across all entities ... Work closely with bookkeeping/accounting to ensure invoices, expenses, and records are accurate and ...

System One

Sales Representative

Chicago, IL · Remote

$90K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

Chicago, IL Type: Full-time Compensation: $90,000.00 Contractor Work Model: Remote Hours: 40.0 ... Basic accounting and bookkeeping skills. * Customer service attitude with a professional and ...

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All JobsBookkeeping Contractor JobsBookkeeping Contractor Jobs in Chicago, IL

Bookkeeping Contractor information

See Chicago, IL salary details

$13

$25

$36

How much do bookkeeping contractor jobs pay per hour?

As of Aug 15, 2026, the average hourly pay for bookkeeping contractor in Chicago, IL is $25.05, according to ZipRecruiter salary data. Most workers in this role earn between $20.29 and $28.46 per hour, depending on experience, location, and employer.

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

To thrive as a Bookkeeping Contractor, you need a solid understanding of accounting principles, experience with financial recordkeeping, and often formal training in bookkeeping or finance. Familiarity with accounting software such as QuickBooks, Xero, or Sage, and relevant certifications like Certified Bookkeeper (CB) or AIPB certification are highly valued. Attention to detail, organizational skills, integrity, and clear communication are key soft skills that help you excel in managing client accounts and deadlines. These skills are essential for ensuring accurate financial records, maintaining client trust, and delivering reliable bookkeeping services on time.

What types of businesses do bookkeeping contractors typically work with, and how does the client relationship usually function?

Bookkeeping Contractors commonly work with a variety of clients, including small businesses, startups, freelancers, and sometimes larger organizations that need extra support during busy seasons. The contractor typically works remotely or on-site on a part-time, project, or retainer basis, depending on the client’s needs. Contractors are responsible for managing multiple client accounts, maintaining regular communication, and ensuring all financial data is up-to-date and compliant with regulations. Building strong, trust-based client relationships is vital, as you may become a key advisor to clients on their day-to-day financial operations.

What is a bookkeeping contractor?

A Bookkeeping Contractor is a self-employed professional who provides bookkeeping services to businesses on a contract basis. Their responsibilities typically include recording financial transactions, reconciling accounts, generating financial reports, and ensuring accurate financial records. Unlike in-house bookkeepers, contractors work with multiple clients and may offer remote or on-site services. They often set their own schedules and rates, making it a flexible career option for those with bookkeeping expertise.

What are popular job titles related to Bookkeeping Contractor jobs in Chicago, IL?

For Bookkeeping Contractor jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Bookkeeping Contractor jobs in Chicago, IL look for?

The top searched job categories for Bookkeeping Contractor jobs in Chicago, IL are:

Bookkeeping Contractor jobs near you
Infographic showing various Bookkeeping Contractor job openings in Chicago, IL as of August 2026, with employment types broken down into 50% Full Time, 33% Part Time, and 17% Contract. Highlights an 83% In-person, and 17% Hybrid job distribution, with an average salary of $52,098 per year, or $25 per hour.

Bookkeeper

CTH Recruiting LLC

Highland Park, IL

$75K/yr

Full-time

Posted 7 days ago

Job description

Bookkeeper

Location: Highland Park, IL – In-Office

Schedule: Monday–Friday, Day Shift

Position Type: Full-Time


About the Opportunity

We’re looking for a detail-oriented Bookkeeper to join a growing construction team in Highland Park. This is a great opportunity for someone with hands-on bookkeeping experience who is organized, accurate, and comfortable working in a fast-paced environment with multiple projects.

The ideal candidate has experience within construction, contracting, or the trades and is familiar with Acumatica.


What You’ll Do

  • Enter and track project expenses, equipment rentals, material costs, and other job-related expenses
  • Process vendor invoices and manage accounts payable and accounts receivable
  • Match invoices to purchase orders and track subcontractor payments
  • Accurately code invoices, receipts, expenses, and job numbers
  • Maintain organized and up-to-date financial records for multiple active projects
  • Complete monthly bank and credit card reconciliations
  • Assist with general bookkeeping and accounting functions as needed


What We’re Looking For

  • 1–3+ years of bookkeeping or accounting experience, preferably within construction, contracting, or the trades
  • Experience with Acumatica preferred; Acumatica Construction Edition experience is a strong plus
  • Experience with accounts payable, accounts receivable, and account reconciliations
  • Familiarity with job costing and construction-related expenses
  • Strong organizational and data entry skills
  • Excellent attention to detail and accuracy
  • Ability to manage multiple priorities and stay organized
  • Reliable transportation to the Highland Park office


Why Join Us?

You’ll be joining a growing construction team that values accuracy, reliability, and people who take pride in their work. This is a full-time, in-office opportunity with a consistent Monday–Friday schedule and the opportunity to play an important role in the company’s day-to-day financial operations.


If you have a solid bookkeeping background and enjoy keeping things organized and accurate, we’d love to hear from you.


Equal Opportunity Employer