Business Networking Events in Chicago

October 19 to October 25, 2026

This Week's Featured Event:

Cashflow Game for Real Estate Investors

Sharpen your real estate, finance, and partnering skills at a friendly session of Robert Kiyosaki's Cashflow Game. You'll play alongside other entrepreneurs and investors while enjoying food provided on-site. It's a relaxed, hands-on way to build investing know-how without the pressure of a classroom. All levels of experience are welcome to join in.

When:

Saturday, October 24 10:00 AM to 1:00 PM CDT

Where:

1945 N Elston Ave Chicago, IL 60647

Cost:

Free

Click here to register

In-Person Events

Women in Tech, Fintech, AI, Startups, Networking & Elevator Pitch

This networking night brings together women in tech, fintech, healthtech, edtech, and AI alongside startup founders and entrepreneurs. Expect an empowering space to share experiences, challenges, and wins while building real connections. Whether you're launching a company or growing your career in tech, come meet professionals who understand the journey.

When:

Monday, October 19 7:00 PM to 10:00 PM CDT

Where:

Ten Cat Tavern 3931 N Ashland Ave, Chicago, IL 60613, USA Chicago, IL 60613

Cost:

Free

Click here to register

Finding Your Niche in Real Estate: Self-Storage Investing

Explore self-storage investing, one of real estate's fastest-growing niches, at this relaxed evening hosted by the Chicago Multifamily Club. Featured speaker Ben Salzberg, COO and Co-Founder of Self Storage Developers, brings over 23 years of experience to share insights on development, fundraising, and what it takes to scale in this asset class. Come connect with local investors too.

When:

Tuesday, October 20 6:00 PM to 8:00 PM CDT

Where:

Avenue Tap & Kitchen 3407 N Paulina St Chicago, IL 60657

Cost:

Free

Click here to register

Chicago Business Matchroom | Referrals, Partners & Local Resources

Meet local professionals, trade referrals, and find potential partners at the Chicago Business Matchroom. It's built for growing your business through genuine connections and local resources rather than stiff small talk. Come ready to share what you do and discover how others in the room might help you grow.

When:

Tuesday, October 20 6:00 PM to 8:15 PM CDT

Where:

HUB116 116 West Hubbard Street Chicago, IL 60654

Cost:

$69

Click here to register

Chicago Tech Startups, Investors, Experts Networking & Pitch Event

Connect with tech startups, investors, and industry experts over an evening built around rapid-fire pitches and real conversations. It's a chance to showcase your idea, meet potential backers, or simply expand your network among people building in the tech space. Come ready to talk shop and make new connections.

When:

Tuesday, October 20 7:00 PM to 10:00 PM CDT

Where:

Franklin Tap 325 South Franklin Street Chicago, IL 60606

Cost:

$9.85 - $39.19

Click here to register

Chicago Data Night: Harper Reed (Former CTO Obama for America)

Join this month's Chicago Data Night featuring Harper Reed, former CTO of Obama for America, as part of an ongoing series connecting data practitioners, academics, and enthusiasts. Hors d'oeuvres and drinks are provided while you dig into the latest in data-driven industry and academic work. A great way to meet others at the intersection of tech and data.

When:

Wednesday, October 21 5:30 PM to 7:30 PM CDT

Where:

TechNexus Venture Collaborative 20 N Wacker Dr 12th Floor, Chicago, IL 60606, USA Chicago, IL 60606

Cost:

Free

Click here to register

Your Sunday FUNday Fall Plans: Bowling + Beers + New Friends! ๐Ÿ‚๐ŸŽณ

Kick off a six-week social bowling league with good vibes, new friends, and zero pressure to be good at bowling. Expect a mix of people in their 20s, 30s, and 40s, post-game hangs at the bar, and weekly trivia. It's a low-commitment way to build your Chicago social and professional circle this fall.

When:

Wednesday, October 21 7:00 PM to 9:00 PM CDT

Where:

Chicago

Cost:

Free

Click here to register

Chicago Healthcare, Pharma & Business Networking Event

Meet established professionals across healthcare, pharma, and business at this Chicago mixer. It's a relaxed setting to swap ideas, build connections, and discover opportunities across these intersecting industries. Come ready to introduce yourself and meet people shaping the local healthcare and business scene.

When:

Wednesday, October 21 7:00 PM to 9:00 PM CDT

Where:

Joy District 112 West Hubbard Street Chicago, IL 60654

Cost:

$9.85 - $21.05

Click here to register

Chicago AI, Tech & Finance Networking Event

Connect, learn, and grow with others working in AI, tech, and finance at this Chicago networking evening. Whether you're building in these spaces or simply curious about where they're headed, it's a laid-back chance to meet people shaping these industries. Come with your questions and your business cards.

When:

Wednesday, October 21 7:00 PM to 9:00 PM CDT

Where:

Joy District 112 West Hubbard Street Chicago, IL 60654

Cost:

$10.25 - $28.31

Click here to register

Business Acumen: Show Up and Stand Out โ€“ Networking, Referrals and Community

Learn how to show up and stand out through networking, referrals, and community building at Polsky Exchange North. Hosted by the Polsky Center for Entrepreneurship and Innovation, this session is a chance to sharpen your business acumen while meeting fellow entrepreneurs. Come ready to connect and build lasting professional relationships.

When:

Thursday, October 22 10:00 AM to 12:00 PM CDT

Where:

Polsky Exchange North 1452 E 53rd St, Chicago Chicago, IL

Cost:

Free

Click here to register

LeadDev Chicago @ Thoughtworks: October 22, 2026

Head to Thoughtworks for an evening of networking and lightning talks on leadership. Organizers will share takeaways from the LeadDev NYC Conference, including favorite sessions and insights, alongside talks like Javiera Lasso on architecture modernization and Dan Snell on AI agent test automation. Beverages and bites are provided, so just bring yourself and an interest in leadership conversations.

When:

Thursday, October 22 5:00 PM to 7:30 PM CDT

Where:

Thoughtworks inc. 200 E Randolph St # 2500, Chicago, IL Chicago, IL 60601

Cost:

Free

Click here to register

Building Trust in AI: Data Governance, Risk, and Responsible Adoption

Join technology, data, and business leaders for a discussion on accelerating AI adoption without compromising governance, compliance, security, or trust. You will dig into data quality and governance as AI enablers, navigating evolving regulations, using AI responsibly with sensitive data, and balancing innovation with risk. A great evening to connect with others tackling these same challenges.

When:

Thursday, October 22 6:00 PM to 9:00 PM CDT

Where:

100 South Wacker Drive 100 S Wacker Dr, Chicago, IL 60606, USA Chicago, IL 60606

Cost:

Free

Click here to register

Chicago Speed Networking | NetworkNite | Business Professionals Event

Forget awkward networking mixers where you hover by the snack table. This speed networking event pairs you with fellow business professionals for quick, focused conversations designed to help you make real connections fast. Come ready to introduce yourself, swap ideas, and walk away with a stack of new contacts worth following up with.

When:

Thursday, October 22 7:00 PM to 9:00 PM CDT

Where:

Recess 838 West Kinzie Street Chicago, IL 60642

Cost:

$36.22 - $39.43

Click here to register

Online Events

AI Startup Pitch Practice: Get Live Feedback From Mentors (virtual)

Your pitch has a problem you cannot hear anymore because you have said it too many times. In this live virtual session, founders pitch and get structured feedback on the spot while everyone else learns by watching. Bring a pitch at any stage, even just an idea, and get real talk on structure, traction, and common mistakes.

When:

Tuesday, October 20 6:00 PM to 7:30 PM CDT

Where:

Online event

Cost:

Free

Click here to register

BOSS NETWORKING - business networking and strategy session

Join a high-level community for business strategists built around the idea that the best plans happen together. Seasoned professionals gather here to refine their processes, trade perspectives, and work through topics like developing key metrics, demystifying your finances, and building a company with lasting impact beyond vision and values. Bring your challenges and your ideas.

When:

Thursday, October 22 8:30 AM to 9:30 AM CDT

Where:

Online event

Cost:

Free

Click here to register

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