Virtual Assistant ChicagoChicago virtual assistants who work the Loop's hours.
Simpalm Staffing is a remote staffing agency for Chicago and Illinois businesses. We place vetted virtual assistants from Latin America on your Central Time day, with a 30-day fit guarantee and no upfront fees.
- Your hours, Central TimeNo overnight handoffs
- All of IllinoisFrom Rockford to Springfield
- Started in about two weeksVetted, interviewed, ready
- 30-day fit guaranteeNo upfront fees
Where a Chicago week starts to crack.
Pick the one that sounds like yours.
01Law firms
Eight hours at the office. Three reach a bill.
A virtual paralegal takes intake, document prep, calendaring and client updates, so more of your day reaches a bill.
- 3.0billable hours in a lawyer's 8-hour day, on average. Source 1: Clio Legal Trends, 2025
02Dental offices and med spas
The phone rings mid-patient. Then it stops.
A patient coordinator answers, books and calls back the patients your front desk can't reach, on your hours.
- 31 in 100dental callers hang up before reaching the front desk. Source 2: Patient Prism, 2026
- 30-35%of calls to med spas go unanswered. Source 3: Zenoti, 2026
03CPA practices
Partners should review returns. Not prepare them.
An experienced tax preparer takes the prep and the data entry, so your partners get back to review, advice and sign-off.
04CFOs and consultancies
Clients pay for your judgment. You do the admin.
A finance assistant handles reconciliations, client prep and follow-ups, so your hours go to the advice clients pay for.
05Business owners
It's 10 p.m. and you're still in your inbox.
A dedicated virtual assistant owns your inbox, calendar and follow-ups on Central Time, so your evening is yours again.
06Property managers
It's the 5th. Rent is late. You're making the calls.
A property management assistant chases rent, logs maintenance and calls tenants back, so the 5th is just another day.
Recognize more than one? The first call sorts out which one to hand off first.
Sources Clio Legal Trends, 2025Patient Prism, 2026Zenoti, 2026
Your day runs on a loop. Get off at your stops.
Inbox, calendar, follow-ups, invoices, the CRM nobody updated. Most of those stops were never yours. A Chicago virtual assistant takes the train; you get off where your work is.
The Loop took its name from the cable cars that once circled downtown; the elevated tracks closed the circuit in 1897.1 Today eight CTA rail routes and 146 stations keep the city moving.2
- ClientsYour relationships and the conversations that win work.
- DecisionsWhat to say yes to. Always yours.
Sources Chicago Architecture CenterChicago Transit Authority
Who hires a virtual assistant in Chicago?
From the Loop to the O'Hare corridor, the businesses that hire us look different and need the same thing: a reliable person who owns the recurring work. Pick a pin to preview the service we place there.
Chicago earned its name as "the city that works" one neighborhood service at a time.1
Not in Chicago? Our virtual assistant services cover Illinois end to end: Rockford, Peoria, Springfield, Champaign and the Quad Cities work the same Central Time day.
Sources UIC LibrarySBA Office of Advocacy, 2025 metro profilesU.S. Census Bureau, Vintage 2025 estimatesCity of Chicago, Department of Technology and Innovation
Real English-Speaking Professionals
Press play and hear them in their own words, in English. Each one is a professional from Latin America who works with US businesses through Simpalm Staffing.
Hear from our clients
Business owners talk about working with Simpalm Staffing, on camera and in their own words. Press play on any card.
An in-house hire, or remote staffing in Chicago?
Remote staffing in Chicago is a different shape of hire: a dedicated person without the payroll, the desk and the search.
| What it takes | In-house in Chicago | With Simpalm Staffing |
|---|---|---|
| What it costs a year | $79,710a yearmean annual wage of an executive assistant in the Chicago metro (executive secretaries and executive administrative assistants), before benefits.1$54,630a yearmean annual wage of an administrative assistant in the Chicago metro (secretaries and administrative assistants, except legal, medical and executive).1 | $26,400 to $36,000a year$2,200 to $3,000 a month, full time (40 hours a week). Sick leave and vacation covered, no interview fees. |
| Search and screening | Weeks of postings, resumes and interviews, on your time. | A skills test, a practitioner interview, two or three finalists in about two weeks. |
| Payroll and benefits | Salary plus benefits, employer payroll taxes and paid time off. | One monthly invoice, after the work is done. We handle payroll. |
| The desk | A seat, a laptop, a license, a parking pass or a Ventra card. | Their own setup. Your logins, scoped to the role. |
| If it is not working | A second search, after the first one already cost you. | 30-day fit guarantee. Not right? We go again, free. |
| Hours | Nine to five in the office. | Nine to five Central Time, from Mexico City, Bogotá, Lima or São Paulo. |
In-house figures are the mean annual wage in the Chicago metro, before benefits and employer taxes. Simpalm Staffing figures are the monthly range on our pricing page, times twelve.
Your assistant works Chicago hours.
Mexico City shares Chicago's clock in winter.1 Bogotá and Lima share it in summer; São Paulo and Buenos Aires run two to three hours ahead, so your whole afternoon overlaps.2 Mexico ended daylight saving time in 2022, outside its northern border strip.3
No overnight handoffs. Read why that matters in Why Your VA Isn't Working: The Hidden Cost of the Wrong Time Zone, and meet the talent pool on our LATAM virtual assistants page.
A skills test. A practitioner interview. You decide.
From our first conversation to your assistant's first day: start to finish in two weeks.
- 1Day 1We listen first
A hiring consultant, not a script. We ask what is breaking in your week, not which title you think you need.
- 2Days 2 to 9A skills test, then a practitioner interview
A Ducknowl assessment scored against the work your role needs, then one on one, in English, with someone who has done this exact work.
- 3Days 10 to 12You meet two or three people
Each with a monthly rate attached. You decide. None right? We go again, free.
- 4Day 14Your assistant starts
On your Central Time day, inside your tools, with onboarding support from us.
Check-ins for as long as they work with you.
Regular check-ins with you and your assistant. One invoice, after the work is done. We handle payroll and time off. Not working in the first 30 days? We find the right person.
- Started in about two weeks
- 30-day fit guarantee
- No upfront fees
- No binding contracts
- Pay after the work is done
Three reads before your first Chicago assistant.
Why Your VA Isn't Working: The Hidden Cost of the Wrong Time Zone
Why a reply that lands while Chicago sleeps costs more than it saves, and what a same-day assistant changes.
Read the article →
Virtual Assistant vs In-House Hire: How to Decide Which One Your Business Needs
When a role needs a desk in the office, and when it needs a reliable person in your software. A decision guide.
Read the article →
What Tasks Can a Virtual Assistant Do? A Delegation Map for Small Business Owners
A practical map of what to hand off first and what to keep. Useful before you decide between part time and full time.
Read the article →Questions Chicago business owners ask us.
Chicago and Illinois
How do I reach your Chicago team?
Call our Chicago number, 312-554-5843, during Chicago business hours, or write to contact@simpalmstaffing.com any time; we reply by the next business morning. Your assistant works remotely on your Central Time day, so nothing depends on a desk downtown.
Will my virtual assistant work Chicago hours?
Yes. Our Latin American talent works your Central Time business day. Mexico City shares Chicago's clock in winter; Bogotá and Lima share it in summer; São Paulo and Buenos Aires run two to three hours ahead, so your whole afternoon overlaps. No overnight handoffs.
Do you provide virtual assistant services outside Chicago, across Illinois?
Yes. We staff businesses across Illinois, from Naperville, Schaumburg and Evanston to Rockford, Peoria, Springfield and Champaign. The assistant is remote, so the city line never matters; the time zone does, and it is the same.
Can my assistant come to the office?
No. Our virtual assistants work remotely from Latin America. If you need someone at a desk in Chicago every day, that is an in-house hire, and we will tell you so in the first call.
Working together
What does a Chicago virtual assistant actually take over?
Inbox, calendar, follow-ups, invoicing support, CRM upkeep, research, travel and the personal admin that spills into the workday. Higher-judgment work, like vendor communication and light project ownership, once trust is built. Decisions and client relationships stay with you.
Is a remote staffing agency the same as a freelance marketplace?
No. A marketplace helps you find one person quickly, with no vetting and no one to call. Simpalm Staffing screens every candidate through Ducknowl, has a practitioner interview them, matches them to the actual problem in your business, and stays after the placement with regular check-ins.
How do you handle confidential information?
Every placement signs an NDA before day one and passes a background check. Access to your systems is scoped to exactly what the role needs, with their own logins, never blanket access.
Part time or full time?
Part time, about 20 hours a week, when the pain is steady but bounded. Full time, about 40 hours, when you are the bottleneck every single day. You can move between them as your workload changes.
Getting started
How fast can we start?
About two weeks from the first conversation to your assistant's first day: we listen, test the skills, interview, and you meet two or three finalists.
What does it cost?
Each finalist comes with a monthly rate attached, so you compare real people. See the Simpalm Staffing pricing page for the full-time range and how the model works. There are no upfront fees and no binding contracts.
What if it is not the right fit?
A 30-day fit guarantee. You are never invoiced in advance, and if it is not working in the first 30 days, we find the right person at no cost.
No Upfront Fees · No Binding Contracts
Just your trust, and a process that delivers real talent. Start with a conversation. We'll listen first, then go to work.
Schedule a Free ConsultationP.S. If you're anywhere near Chicago, let's meet over deep dish. Tell us your corner of the city and we'll get to know each other the way this town does: over a good meal and a real conversation.
Simpalm Staffing provides staffing. We do not provide legal, tax, medical or financial advice, and our professionals work under your direction and review, within the access you grant. Owner scenarios on this page are illustrative. The neighborhoods named describe the kinds of businesses we serve, not client lists. "The L" and "Ventra" are marks of the Chicago Transit Authority; "Metra" is a mark of the Commuter Rail Division of the RTA. Simpalm Staffing is not affiliated with or endorsed by them.