Bookkeeping · Chicago, IL

Bookkeeping built for
Chicago businesses.

AI-powered, expert-reviewed bookkeeping for Chicago businesses of every size — from solo founders and corner shops to multi-location restaurants, growing manufacturers, finance firms, and logistics operations. Same dedicated team, same Portal, same monthly close.

★★★★★ 5.0 on Google · 100+ businesses helped · QuickBooks & Xero certified
Built for Chicago

From the trading floor
to the loading dock.

Chicago runs on more than one industry, and at every size — from solo operators and one-location shops to mid-market manufacturers and trading firms. We've handled books for them all, including the Illinois-specific quirks the national firms miss.

Finance & FinTech

Trading desk reconciliation, FCM accounting, prop firm books, futures/derivatives margin tracking. Built for Chicago's trading and FinTech ecosystem.

Prop · brokerage · FinTech

Manufacturing & Industrial

Job costing, materials vs. labor, COGS rollups, multi-state sales tax for shipping. From small machine shops to mid-sized industrial operations.

Job costing built-in

Real Estate

Property-level books, syndications, K-1 distributions, depreciation schedules. From single-property LLCs to Cook County multi-entity portfolios.

Multifamily · commercial · STR

Restaurants & Hospitality

Daily sales reconciliation, food cost tracking, tip pooling, multi-location rollups. From West Loop tasting menus to Lincoln Park neighborhood spots.

Multi-location ready

Logistics & Distribution

Multi-state nexus, freight expense allocation, fuel tax, fleet depreciation, warehouse cost rollups. Built for Chicago's role as the country's freight hub.

Multi-state freight ready

Professional Services

Trust accounting, retainer recognition, partner draws — built for law firms, consultancies, and agencies across the Loop, River North, and Fulton Market.

Law · consulting · agencies
The process

Live in 14 days.
Reviewed every month.

No 90-day onboarding nightmare. No mystery process. Here's exactly what working with us actually looks like.

01

Discovery call

30 minutes. We review your current setup, walk you through the Yesler Portal, and quote a clear monthly engagement scoped to your business — before any work begins.

02

Onboarding

We connect to your bookkeeping software (or set you up fresh in QuickBooks/Xero), build your Portal, and your dedicated Illinois-savvy team learns your business. Live in 14 days.

03

Monthly close, 3-tier review

AI handles the first pass. Your dedicated specialist reviews and catches edge cases. Senior management or our in-house CPA signs off. You see every step in the Portal.

Why Chicago picks us

Illinois-aware bookkeeping.
Real humans on every account.

National firms treat you like a number. Small local shops disappear when their one bookkeeper takes vacation. We're built differently.

Illinois-specific expertise

We handle Illinois Annual Report filings with the Secretary of State, navigate Chicago's 10.25% sales tax stack (state + county + city + RTA), manage Personal Property Replacement Tax (PPRT) for corporations and pass-throughs, and understand Cook County's specific business taxes and reporting that catch national firms off-guard.

Three layers of review on everything

AI handles the repetitive work. Your staff specialist checks it and handles edge cases. Senior management or our in-house CPA signs off before anything is finalized. No single point of failure, no "trust us" black box.

Multi-platform specialists

QuickBooks Online & Desktop, Xero, FreshBooks, Wave, Sage. We work where you already do — your books stay where your CPA, lender, and tax software expect them.

Central business hours

Your dedicated team is available during CST. Same-day responses on weekday messages. No outsourced call centers, no 3am email chains.

Right-sized for your business — and scales with you

Whether you're a one-person shop, an owner-operator with a small team, or a multi-entity company outgrowing your last firm, we scope every engagement to where you actually are. As you grow, your team stays the same — we scale alongside you instead of handing you off to a different tier.

Free 30-min demo

Built to scale with your business.

Whether you're a solo founder finally getting your books in order or a multi-entity company outgrowing your last firm — we'll show you what life looks like with Yesler running your back office.

  • Same dedicated team as you grow
  • Free Portal walkthrough
  • Month-to-month, cancel anytime
  • Books stay in your software
Book Your Free Demo →

We're a Loop-based consulting firm that grew from 3 to 22 people in 18 months. Our old bookkeeper couldn't keep up — and didn't understand Illinois replacement tax or Chicago's sales tax stack. Yesler took over, and our quarterly cleanup nightmare became a non-event. Their Portal means I actually know what's happening with our finances now.

Jennifer M. · Managing Partner · Consulting firm · Chicago, IL
FAQ

Questions Chicago business owners ask.

Honest answers to what we hear before every demo.

Are you actually based in Chicago?
We're a US-based remote team that specializes in serving Illinois businesses. Every team member is in the US, and your dedicated bookkeeper is available during Central business hours. We've handled bookkeeping for Chicago companies across finance, manufacturing, restaurants, logistics, real estate, and professional services — we know the Illinois-specific quirks national firms miss. If meeting in person matters to you, we can also arrange that.
Do you handle Illinois Annual Report and replacement tax filings?
Yes — every year, included with your engagement. We file your annual report with the Illinois Secretary of State, manage Personal Property Replacement Tax (PPRT) filings (2.5% for C-corps, 1.5% for S-corps, partnerships, and trusts), and track every deadline so you never get hit with an administrative dissolution notice. We also handle the Chicago-specific business taxes that catch out-of-state firms.
We're a prop firm / trading shop — can you handle the complexity?
Yes. Trading desk P&L reconciliation, FCM and clearing statements, margin tracking across futures and options, mark-to-market accounting for 1256 contracts, trader tax status determination, and the Section 475 election timing. We've worked with Chicago prop firms, FCMs, and the CTA/CPO complex.
How does Chicago's sales tax stack actually work?
Chicago has the highest big-city sales tax in the country at 10.25% — that's Illinois state (6.25%) + Cook County (1.75%) + Chicago city (1.25%) + RTA (1%). Suburban Cook is lower (typically 8–9%), and collar counties are different again. We track nexus, filing schedules, and remit correctly across every jurisdiction you operate in. If you ship interstate, we handle multi-state economic nexus too.
We're already in QuickBooks Desktop — is that a problem?
Not at all. A lot of established Chicago manufacturers, logistics operators, and service businesses still run QBD because it works. We work in it daily. We'll only recommend migrating to QuickBooks Online if it would genuinely serve you better (multi-user remote access, better integrations, etc.) — and if so, we handle the entire migration. No pressure either way.
I'm a solo founder / small business — am I the right fit?
Yes — small businesses are a big part of who we serve. Whether you're a solo founder finally getting your books in order, an owner-operator running a small shop, or a 1–10 employee business that's outgrown DIY QuickBooks, we're built for you. You get the same dedicated team, the same Portal, the same three-tier monthly close as our largest clients — scoped to where you actually are today. As you grow, we scale with you; we don't push you onto a different tier or hand you off mid-relationship.
How fast can you actually start?
Live in 14 days for most Chicago clients from the day you sign on. Onboarding takes about a week (connecting to your software, building your Portal, getting your team up to speed on your business). Catch-up work — if you need 6 or 12 months brought current — runs in parallel and finishes within 30–45 days for most cases. If you need it faster because of a lender, audit, or IL Department of Revenue deadline, tell us during the demo; we can usually accommodate.

Ready to get your Chicago books in order?

Tell us about your business. We'll show you what life looks like with an Illinois-aware bookkeeping team running your back office — built for businesses of every size, from solo founders to multi-entity companies.