WestwardAI Consulting

Local market data · Bookkeepers · Chicago

AI for bookkeepers in Chicago

The Chicago metro area had 1,407 bookkeepers in 2022, the 4th most of 387 US metros and 3% of all in the country. They employed 8,067 people at an average of $58,190 a year. 93% have fewer than 10 staff, so the same few people answer the phone, book, follow up and do the paperwork. Those are the jobs AI tools take on today.

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Bookkeepers in Chicago vs the US

Chicago metroUnited States
Businesses1,40746,452
People employed8,067247,793
Average staff per business5.75.3
Average yearly pay per employee$58,190$55,181
Share with fewer than 10 staff93%92%

Pay here is 5% higher than the national average for bookkeepers, so every hour of staff time costs more to spend on admin. The average bookkeeper here has 5.7 people on payroll, 7% higher than the US figure of 5.3.

How big bookkeepers in Chicago are

Fewer than 5 staff1,126 (80%) US 78%
5 to 9177 (13%) US 13%
10 to 1946 (3%) US 5%
20 to 4941 (3%) US 2%
50 or more16 (1%) US 1%

Businesses with paid employees, by number of employees, March 2022.

Bookkeepers by county in the Chicago area

Cook County has the most, with 754 of the metro's 1,407 (54%). Among the 10 big metros on this page, Chicago ranks 9th for average pay and 3rd for the share of small firms.

CountyBusinessesEmployeesAvg pay
Cook County7543,160$68,836
DuPage County2283,135$53,635
Lake County120320$59,178
Will County94448$39,730
Kane County69504$58,141
McHenry County55177$36,825
Lake County45188$41,415
Porter County1228$33,000
DeKalb County1152$21,212
Kendall County1135$22,743
Grundy County718$31,833

Census withholds pay where few firms would make it identifiable.

Where AI helps a bookkeeper first

A bookkeeper gets the most from AI by handing off the repetitive parts of the month: chasing receipts, suggesting categories for odd transactions, reminding clients before close and answering the same questions. The bookkeeper still reconciles and signs off on the books. Westward can build the surrounding pieces, and a person approves anything that goes out.

What your team's admin hours cost in Chicago

Change any number. The starting values are the Chicago averages above; the hours and the share are yours to set.

Those hours cost you$67,200 a year

The share you would hand off$20,160 a year

Hours your team gets back720 a year

See what we would build for this

Guides for bookkeepers, one job each

Bookkeepers in other big metros

MetroBusinessesAvg payRank of 387
Los Angeles2,607$62,4552nd
New York3,295$65,3961st
Miami2,161$55,7803rd
Dallas1,168$65,8075th
Houston1,037$65,7417th
Atlanta1,120$59,8656th
Washington879$90,3948th
Philadelphia614$72,03015th
Boston525$78,58019th

Where these numbers come from

From the U.S. Census Bureau, County Business Patterns 2022 (released 2024), industry code NAICS 541219 (Other accounting services (incl. bookkeeping)), for the Chicago-Naperville-Elgin, IL-IN metro area (13 counties). It counts businesses with paid employees in March 2022, so solo owners with no payroll are not in it. Average pay is total yearly payroll divided by employees. The calculator uses 50 working weeks and 2,080 hours a year. Page checked 2026-11-12.

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A free 30-minute call. You leave knowing which part of your bookkeeper to hand to AI first, what we would build, and roughly how long it takes.

Related businesses in Chicago

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