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Step-by-Step Guide to Hiring a Bookkeeper for Your Chicago Small Business

Hire a Bookkeeper | By Lily Wilson | 2025-09-19 07:15:48

Step-by-Step Guide to Hiring a Bookkeeper for Your Chicago Small Business

Bookkeeping is the financial foundation of every successful small business. In a fast-paced business environment such as Chicago's, bookkeeping is even more valuable. That is why entrepreneurs are generally on the hunt for "best certified bookkeepers in Chicago, IL." 

As more than 70 percent of small businesses in Chicago today are using bookkeeping services, the need to hire online bookkeeping services Chicago for your business rises significantly, as it is essential for being successful in this competitive marketplace. 

Why is Bookkeeping Essential for Small Businesses in Chicago?

Bookkeeping is not simply recording payments and receipts. For small businesses, bookkeeping includes recording all transactions, managing payroll and payments to vendors, preparing financial statements, and ensuring compliance with applicable federal tax, Illinois tax, and city tax. An experienced bookkeeper at The Fino Partners can help you:

  • Keep up to date on cash flow
  • Identify trends in profit and loss
  • Get ready for tax season without panic
  • Help with loan or grant applications with accurate records
  • Avoid costly compliance errors

In the end, a professional bookkeeper provides you with more hours in your week and removes the time-consuming administrative tasks from you so you can focus on growth and strategic planning.

Online Bookkeeping Services in Chicago: What Makes Them Special?

The ever-increasing growth of technology has only accelerated the trend toward online bookkeeping services Chicago for the small business:

  • More Flexible and Convenient: A client and bookkeeper be able to coordinate financial information on cloud-based software anytime and from anywhere
  • More Affordable: Less massive office setups and scalable packages often ensure competitive pricing and predictable costs.
  • Adoption of Technology: From expense tracking to receipt scanning and a reporting dashboard, it gives the business owners real-time, relevant, and meaningful information.
  • Greater Access to Talent: With virtual bookkeeping services, you can find and hire professionals from a whole host of candidates located outside your city or region.
  • Timeliness and Precision: Automating processes reduces errors due to human intervention while also speeding up each bookkeeping cycle.

Hire a bookkeeper for a small business in Chicago with The Fino Partners to carry out everyday bookkeeping and compliance needs.

Steps to Hire a Bookkeeper for Your Small Business in Chicago

Below are the steps to hire the best certified bookkeepers in Chicago, IL, with The Fino Partners:

1. Assess your business needs

  • There are some steps to follow in determining whether you need full bookkeeping services or just selected services like payroll, taxes, or compliance assistance. You will also need to determine if you want ongoing support (monthly or weekly) or a project-based schedule to catch up or to assist with year-end work. 

2. Craft a realistic budget

  • For a point of reference, most bookkeepers in Chicago charge between $25 and $50 per hour, depending on their experience and services, with monthly packages starting around $300 for basic plans, and exceeding $1,000 for more extensive plans. 
  • Online bookkeeping services usually have flat monthly rates and, in many cases, contracts that expand as you grow.

3. Research and short list providers

  • Use online platforms such as Yelp, LinkedIn, Google, and industry-based directories to find and filter for a certified bookkeeper near you or online. Search for terms like "online bookkeeping services Chicago" or "best certified bookkeepers in Chicago, IL," to shorten your list.

4. Interview the candidates 

  • Check their credentials, years of experience, and familiarity with the accounting tools you are using.
  • Discuss their communication practices, availability, and how they will handle urgent tasks and/or questions.
  • Be sure to ask for references as well as more detailed proposals to help you gain more clarity.

5. Confirm technology compatibility

  • Pick a bookkeeper who embraces leveraging cloud service platforms that connect with your bank account, point of service, payroll, and tax software, if you have that. This can enable an efficient flow of data and paperwork.
  • Look for secure document portals and real-time dashboards that can help you work faster and more securely.

6. Determine the scope of services and sign the contract

  • Make sure to establish clear expectations with your bookkeeper on things like how often you'll receive reports, what deliverables they will provide, how they will charge you, when review meetings will take place, etc. 
  • Be sure to clearly establish how onboarding and transition will work, especially if you're moving from another provider.

7. Onboard and communicate

  • Provide access to any financial data you have shared over the past few months, as well as providing secure login access. 
  • Establish a communication routine that meets your needs. 
  • The frequency of communicating will depend on how you plan to use this bookkeeper in your accounting process, monthly reports, weekly check-ins, etc. 

Trust your bookkeeper, but be sure to review reports carefully and don't hesitate to ask for clarification, making sure you're aligned on understanding the report and report metrics.

What Can You Expect from a Bookkeeper in Chicago?

Once you bring a professional bookkeeper onto your team, you would reasonably expect each of the following things:

  • Categorization of transactions and reconciliation of all accounts.
  • Invoice management and accounts receivable follow-up with customers.
  • Payments to vendors and accounts payable follow-up.
  • Simple and easy generation of profit and loss statements, balance sheets, and cash flow reports.
  • Handling payroll and compliance filings.
  • Communication to respond to your questions about finances or to resolve discrepancies.

Some certified bookkeepers at The Fino Partners may assist you with tax filings, sales tax obligations, or provide some kind of audit-level support.

Benefits of Using Online Bookkeeping Services in Chicago for Small Businesses

The advantages of hiring an online bookkeeper with The Fino Partners include:

  • Improved efficiencies and eliminated manual data entry.
  • Instantaneous access to the financial information on the cloud for the authorized business owner and staff.
  • A reduced chance of errors by automatic processes and checking on systems in real time.
  • Less paper accumulation and quicker turnaround with billing and payments.
  • An opportunity to redirect focus toward a growing business rather than monotonous bookkeeping duties.

With the help of automated technology, automatic bank feeds, expense classification, and storing receipts received online or by email, small businesses can have accurate, updated financials with a reduced burden level.

Understanding Pricing for Bookkeeping in Chicago

Here’s how typical fee structures may shape up in some average local situations:

  • If you select a basic monthly bookkeeping plan, you should expect to pay at least $300. More premium or all-in plans (including payroll, tax prep, and full report) went from $800 to $1,200 or more each month.
  • Hourly rates for Chicago-based bookkeepers are typically between $25 - $50. Some bookkeepers, especially those with certifications or particular experience, may charge more. However, once you find the bookkeeper that fits your company, they aren’t charging you to worry about errors, but rather to provide accuracy and knowledge.
  • Custom packages will allow you to increase and decrease service as your business grows and changes.

Hiring a bookkeeper for your small business in Chicago may be one of the best investments of your time. Be sure to explore online bookkeeping services, but most importantly, look for some of the best certified bookkeepers in Chicago, IL. 

Related Resources

Remember, the point of all of this is guaranteeing your records are legit, taxes are on time, and your small business has clarity and availability to thrive. If you choose your bookkeeper wisely, you will have a quality tactical advisor in accounting, giving you energy to focus on customers and innovation. 

Contact The Fino Partners today to hire a bookkeeper for a small business in Chicago.

Frequently Asked Questions (FAQs)

Online bookkeeping offers real-time accessibility, cost savings, automation, and a wider pool of certified professionals, enabling businesses to scale their services easily and efficiently.

When selecting the right bookkeeper for you, you should look into their credentials, client reviews and testimonials, level of proficiency in software, knowledge of local regulations, upfront, transparent pricing, and communication.

You can predict hourly rates to run anywhere from $25-$50 per hour and monthly packages to run anywhere from $300-$1,200+, depending on the level of services and expertise.

If you are tech-savvy and looking for a convenient option, you will likely prefer an online bookkeeper. If you want to have a relationship and/or need local in-person expertise, you might be better served with an in-person bookkeeper and face-to-face meetings.

If you are set up in a cloud system, your new bookkeeper may be able to be onboarded and doing business in a few days once the documents and access have been arranged by you.

Yes, most certified bookkeepers can help clients or create documents for audits and preliminary tax prep in preparation for an accountant to present to the owner. Some are able to sign documents to represent you in the audit process.
Aishwarya-Agrawal

Lily Wilson

A seasoned financial writer, Lily Wilson specializes in virtual CFO services and outsourced accounting solutions. Her articles guide readers through financial strategy, reporting, and accounting outsourcing with precision and insight. Lily’s expertise helps businesses streamline their financial processes, setting them up for sustained success.

Why Choose The Fino Partners?

With Fino partners you get more than just accounting and bookkeeping in the USA. You get an accurate, clear process that makes you satisfied. We made money management easy so you can grow your business instead. The advantages of utilising Fino partners for accounting outsourcing USA are:

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