WinningWithAI.com / Find a Seminar / Illinois
Winning With AI in Chicago, IL
Winning With AI is coming to Chicago. In one live evening, Chicago business owners and their teams see exactly how to use AI to get customers faster, follow up before competitors do, run smarter marketing, and hand the paperwork off to machines. Pre-register below to hear the date first.
Coming soon to Chicago, IL. The date and venue are not set yet. Pre-register to be the first alerted when they are.
Pre-register for Winning With AI in Chicago
What is the Winning With AI seminar in Chicago, IL?
Winning With AI in Chicago is a live, in-person evening built to show local business owners and teams how to use AI to transform their work. Mike Filsaime teaches how to get customers faster, follow up better, market smarter, and cut through busywork. Coming soon to Chicago, pre-register to hear first.
- Format: Live, in-person evening built for Chicago and Chicagoland business owners and teams.
- Instructor: Mike Filsaime, pioneer in AI and online business, founder of Groove, Kartra, WebinarJam, and EverWebinar.
- Investment: Early-bird seats with money-back guarantee. Exact price comes at announcement.
- For: Chicago owners, managers, and employees. No tech experience needed. No coding. Plain English.
- Why now: The fastest Chicago businesses are already using AI to land customers faster and get more done. This shows you how to do it.
The Winning With AI seminar in Chicago, explained
Winning With AI in Chicago is a live, hands-on evening built to show local business owners and teams how to make AI work in real business every day.
You watch it happen on the problems Chicago businesses face from Monday through Friday. A customer question answered in seconds instead of hours. A follow-up sent before a lead goes cold and moves to a competitor. A week of social posts and emails created in one afternoon instead of spread across the month. The invoices, scheduling, time tracking, and payroll that eat your week, handled by AI in minutes instead of hours.
You leave knowing exactly which tools to use, how to set them up in plain English, and which move to make first thing Monday morning. No theory. No waiting. Just the moves that work for Chicago businesses right now.
Is AI worth it for a small business in Chicago, Illinois?
Short answer: absolutely. You find out why in one evening instead of spending months figuring it out on your own.
Chicago is full of businesses that know how to work hard, but hard work alone is not the same as working smart anymore. The owners and teams winning right now are the ones who moved their busywork to AI, so they can focus on what only a human can do. The ones who are not using AI yet are watching their faster competitors pull customers away.
This session shows you that exact move, step by step. You leave with practical AI moves that land customers faster, keep your follow-ups on time, get a week of marketing built in an afternoon, and take the payroll and scheduling paperwork off your desk, so you and your team get more done and stay ahead of the shop across the street. One evening for under $100 that saves you five to ten hours every week is a no-brainer, especially backed by a money-back guarantee.
A practical AI seminar built for Chicago businesses
Winning With AI Chicago is built for the businesses that actually make this city run, not a national audience watching from their couch.
Chicago is a logistics hub, a rail and shipping center for the Midwest, a manufacturing and trades powerhouse, a healthcare and professional services economy, and a restaurant and hospitality industry all at once. From the tradespeople in Bridgeport to the restaurateurs in Pilsen, from the consulting shops and corporate offices in the Loop to the creative agencies and startups in Wicker Park and Logan Square, every type of business feels the exact same pressure right now. Customers want faster answers. Competitors are already using AI to give it to them. Winter does not slow down business, it makes it harder to keep up.
This is not a conference about the future of technology. It is a working session built on the real problems Chicago owners, managers, and their teams are solving right now, today, every single week.
What Chicago attendees walk away with
- Get customers to respond faster. Set up AI that writes replies, quotes, proposals, and follow-ups in seconds, so a Chicago customer never sits waiting for an answer while a competitor is already closing the deal.
- Follow up before the lead goes cold. Put follow-up on autopilot. Every prospect and past customer hears from you on time without you having to remember or chase it down yourself.
- Run a month of marketing in one sitting. Turn one idea into a full week of emails, social posts, offers, and content, so your best message hits while people are still thinking about you, not weeks later.
- Hand the paperwork and admin to AI. Give invoices, scheduling, time tracking, and forms to AI. The busywork that eats your Friday afternoon gets done in fifteen minutes.
- Get your team more productive in their role. Learn the AI habits that make every person on your team faster at their job, so you get a week of output in three days.
- Stay ahead in a competitive Chicago market. Walk out with the same moves the fastest Chicago businesses are using right now, so you set the pace instead of catching up every quarter.
Who the Chicago seminar is for
Chicago owners and founders
You run the show, and every hour costs real money.
- Land more customers without hiring more people
- Get payroll, quotes, and admin work off your plate permanently
- Stay a step ahead of competitors who have not figured out AI yet
Managers and team leads
You want to be the person who makes your team faster.
- Cut the busywork out of your day and your team schedule
- Hand your boss work that looks like it took three days when it took one
- Become the person on the team who knows AI and how to use it
Employees ready to level up
You want to make yourself indispensable.
- Get through your daily tasks in half the time you used to
- Show your team new ways to work smarter
- Prove you can do more with the same hours
A live seminar vs. free videos vs. an online course
| Winning With AI seminar | Free online videos | Self-paced AI course | |
|---|---|---|---|
| Format | Live and in-person in Chicago | Pre-recorded clips, watched alone on your screen | Self-paced modules you work through over weeks |
| Built for Chicago business | Yes, built on problems Chicago businesses actually face | No, generic content scattered everywhere online | Rarely, aimed at a broad national audience |
| Ask a question when you are stuck | Yes, ask it out loud in the room and get an answer | No, you are on your own with no one to help | Maybe, in a forum, days later if at all |
| See real work built live from start to finish | Yes, live demos you can actually follow and understand | Sometimes, and hard to understand or replicate | Sometimes, often outdated by the time you watch it |
| Time to your first working result | One evening, using it Monday morning | Weeks hunting through videos hoping you find it | Weeks to months of modules before anything works |
About Chicago, IL
Chicago is a city that knows what it takes to rebuild itself and come back stronger. From the manufacturing base that built the city in the 1900s, to the finance and corporate world that powered it through the 20th century, to the tech, healthcare, and professional services economy that drives it today, Chicago does not wait for permission.
Whether you run a trade shop working in a kitchen or on a job site, a healthcare practice, a restaurant, a logistics operation, a consulting firm, a retail shop, or a professional services office, Chicago is where the work gets done and where customers expect speed. The winters are long, the competition is real, and the business owners winning are the ones who work smarter with the hours they have.
Winning With AI brings that same working-smarter mentality to Chicago in one live evening, so local owners and teams can put AI to work immediately and stay ahead of competitors who are still figuring it out.
How Chicago businesses are using AI right now
The Chicago businesses pulling ahead fastest right now are the ones who moved first on AI.
A Pilsen restaurant owner builds a week of marketing in an afternoon and fills tables faster through the slow season. A Bridgeport contractor pulls out of a job site and turns voice notes into a clean, detailed quote before the sun sets, so the customer decides the same day. A Loop consulting firm sends clients same-day summaries and reports instead of two-day turnarounds, so they book follow-up meetings faster. A Wicker Park shop owner gets one morning email with yesterday sales, payroll, cash flow, and customer inquiries instead of logging into five different systems and taking an hour to piece it together. A healthcare practice answers patient questions after hours without hiring a night staff.
None of it requires hiring a tech team or six months of setup. It requires the handful of AI moves that actually work for real business, which is exactly what Winning With AI Chicago shows you how to build and put to work.
Headlined by Mike Filsaime
Winning With AI Chicago is headlined by Mike Filsaime, a pioneer in the AI and online business world and the founder of Groove, Kartra, WebinarJam, and EverWebinar. Hundreds of thousands of businesses around the world use his platforms to run their operations, host their events, manage their teams, and sell their products every single day.
He is known for one thing above all: taking tools and technology that look complicated on the surface and breaking them down into the moves any business owner can actually execute without a computer science degree. No jargon. No theory. No watered-down explanation. Just the steps that work.
In Chicago, Mike brings that same approach to AI and walks local business owners and teams through the exact moves they can put to work immediately, with time for real questions and a focus on examples you can take home and use in your business the next morning.
People who have seen Winning With AI in action
He'll not only make it simple, he'll make it very profitable.
When I saw what Winning With AI could do, I knew we had to move fast. Work that used to drag out for three months now gets delivered by my team in two or three days.
I'm a tougher critic, but Winning With AI blew me away. One idea showed me how to save thousands of dollars a month.
I had no coding experience. No technical background. Nothing. After seeing how to use AI in plain English, I built software and workflows that completely changed my company.
Winning With AI is coming to Chicago
We have not set the Chicago date yet. Pre-register and you will be the first to know when we do, before seats go on sale to everyone else.
Pre-register for Winning With AI in Chicago
Winning With AI Chicago: frequently asked questions
What is the Winning With AI seminar in Chicago?
It is a live, in-person evening built to show Chicago business owners and teams how to use AI to get customers faster, follow up better, market smarter, and cut through the paperwork that eats your week. You leave with specific AI moves you can use the next day.
When is the Chicago Winning With AI seminar?
Winning With AI is coming to Chicago. Pre-register on this page to hear the date and location details first, and to lock in early-bird pricing when the event is officially announced.
Do I need AI or tech experience to attend the Chicago seminar?
No, none at all. If you can use email and a web browser, you can follow every minute. Winning With AI Chicago is taught in plain English with no coding and no technical jargon.
Who should attend Winning With AI in Chicago?
Any Chicago or Chicagoland owner, manager, or employee who wants to get customers faster, follow up better, market smarter, and cut busywork. It fits trades, restaurants, shops, offices, healthcare practices, consulting firms, and their teams.
Is Winning With AI useful for a small Chicago business?
Yes. Every example is built for small local businesses and teams, so you leave with moves a single-location shop or small team can use Monday morning, not enterprise software you will never touch.
What will I be able to do after the Chicago seminar?
You leave able to answer customers in seconds, keep every lead followed up, build a month of marketing in one sitting, take payroll and scheduling off your plate, and get more done than you did before.
Who is teaching the Chicago Winning With AI seminar?
Mike Filsaime, a pioneer in AI and online business who founded Groove, Kartra, WebinarJam, and EverWebinar. He is known for making complex tools simple for business owners.
How much will the Chicago seminar cost?
Pricing will be announced when the Chicago seminar date is locked. Pre-register now to get early-bird pricing and hear all the details first.
How do I pre-register for the Chicago seminar?
Use the pre-register button on this page to get on the list. You will be first to hear when the Chicago seminar date is set and first to lock in early-bird pricing.