2026 Boss Up! Conference - Chicago

You are one connection away from your next level, and this is the room where it happens.
About this Event

Boss Up! Conference - Chicago

Date: October 10, 2026

Hey, Boss Chick, Hey! Get ready to level up your game at the Boss Up! Conference in the vibrant city of Chicago.

Boss Up! Weekend begins Friday evening and concludes Sunday afternoon. HOWEVER...

The Boss Up! Conference is a one-day implementation experience for ambitious women who are ready to stop watching from the sidelines and start closing deals. Whether you are a seasoned entrepreneur, a corporate boss building your exit plan, or just starting your business, this day was designed to give you the playbook, the people, and the push to move.

This is not a 1500 dollar luxury summit where you never meet the speaker. This is not a 10,000 person expo where you just shop. This is Chicago. Intimate, actionable, and built for real results.

What to expect:

You will start the day with a warm welcome and opening ceremony with Boss Chicks International Founder and CEO Aisha Isreal. You will get clear on how to maximize every moment.

Then get ready to be challenged and empowered by our keynote speaker Dr. Yoli Cox, TEDx speaker and leadership powerhouse. She will help you crush limitations and step boldly into your next level of business and leadership.

After that we dive into the Boss Labs, three hands-on workshops built for immediate implementation. Learn how to price for profit, how to land corporate clients through supplier diversity, and how to use AI to run your business like a team of five even if it is just you.

Midday we break for our signature experience. If you have a VIP Experience ticket, you will join us for the exclusive VIP Power Lunch. This is your deal room. Enjoy a plated lunch while building meaningful relationships with ambitious women from across the region. Your next business bestie, mentor, client, or collaborator could be sitting at your table. VIP also includes front row seating and a chance to be selected for a live hot-seat business audit.

The afternoon brings powerful networking, vendor shopping with Black women owned brands, and our closing accountability session where you will be matched with your 30-day Boss Pod so the momentum does not end when you leave the hotel.

Tickets:

General Admission is 75 dollars and includes all keynote sessions, Boss Labs, networking, vendor marketplace, and your Boss Up Playbook.

VIP Experience is 165 dollars and includes everything in General Admission plus exclusive VIP Power Lunch, front row seating, hot-seat consideration, and VIP gift bag.

This event is in person, no refunds, and space is limited at this venue.

You have waited long enough. It is time to Boss Up.

Saturday's Agenda

🕑: 09:30 AM - 10:30 AM
VIP Check-in

Info: VIP Ticket purchase required. Start your day with early entry and preferred seating in the main meeting room, while connecting with other ambitious women from across the region. Build meaningful relationships, exchange ideas, and set the tone for a day of learning, collaboration, and growth. Your next business bestie, mentor, client, or collaborator could be sitting at your table.

🕑: 10:00 AM - 10:30 AM
General Admission Check-in
🕑: 10:15 AM - 11:00 AM
Welcome & Opening Ceremony

Info: The Boss Up! Conference officially begins! Join Boss Chicks International Founder & CEO Aisha Isreal for opening remarks, conference highlights, and an inspiring welcome that will prepare you to maximize every opportunity throughout the day. Dr. Yoli Cox
Get ready to be challenged, encouraged, and empowered by TEDx speaker Dr. Yoli Cox. Through powerful storytelling and practical wisdom, Dr. Cox will inspire you to overcome limitations, embrace your purpose, and boldly pursue the next level of your leadership, business, and life.

🕑: 11:00 AM - 11:40 PM
Workshop #1

Info: Choose a breakout session designed to provide practical strategies you can immediately apply to your business or career. Led by an experienced industry professional, this interactive workshop will equip you with actionable tools for growth and success.

🕑: 11:45 PM - 12:20 PM
Workshop #2

Info: Continue building momentum with another engaging workshop focused on developing the knowledge, confidence, and skills needed to elevate your business. Expect practical takeaways, real-world examples, and opportunities for discussion.

🕑: 12:30 PM - 01:15 PM
VIP Lunch with Cheryl Branch

Info: VIP ticket purchase required. Lunch with Cheryl Branch in the VIP Lounge. Meal and Beverages provided.

🕑: 12:30 PM - 01:30 PM
Lunch Break

Info: Take a well-deserved break to enjoy lunch while continuing conversations with fellow attendees, speakers, vendors, and sponsors. Some of the best business opportunities begin over a shared meal.

🕑: 01:30 PM - 02:10 PM
Workshop #3

Info: Dive deeper into the topics that matter most to today's entrepreneurs. This session is designed to provide fresh perspectives, proven strategies, and practical solutions you can begin implementing right away.

🕑: 02:15 PM - 02:55 PM
Workshop #4

Info: End the workshop series with another high-impact learning experience that will challenge your thinking, strengthen your leadership, and prepare you for your next level of success.

🕑: 03:00 PM - 03:15 PM
Brain Break

Info: During this time, conference attendees are invited to shop with our vendors and possibly grab a quick bite to eat at a nearby restaurant or snack shop.

🕑: 03:15 PM - 04:15 PM
Panel Discussion

Info: Hear directly from accomplished entrepreneurs and business leaders as they share honest conversations about building successful businesses, overcoming obstacles, making difficult decisions, and creating lasting impact. Bring your questions for this engaging discussion.

🕑: 04:20 PM - 04:50 PM
Keynote

Info: Our closing keynote will leave you motivated, focused, and equipped to take action. Expect powerful insights, practical encouragement, and a compelling reminder that your goals are achievable when preparation meets purpose.

🕑: 04:50 PM - 05:00 PM
Closing

Info: As the conference concludes, we'll celebrate the day's accomplishments, reflect on key lessons, and challenge you to put what you've learned into action. The conference may be ending, but your next chapter is just beginning.