Win Big Live

Chicago’s Wildest Live Game Show Experience

Welcome to Win Big Live

Spin, Pick, and Win

Unpredictable games. Huge rewards. Total fun.

Play for the Big Bucks

Every game night has up to $5,000 in prizes on the line.

Step Into the Spotlight

Get randomly chosen and play live on stage for cash!

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About Game Show

Win Big Live

Get ready for a one-of-a-kind, high-energy, interactive game show experiencelive at the Madison Street Theater in Oak Park, just minutes from downtown Chicago! At Win Big Live, you’re not just watching the show… you’re part of it.

Each monthly show brings exciting challenges, real-time voting, audience participation, and the chance to win up to $5,000 in prizes during every game night. One lucky event each year features the SUPER Win Big Live, where a contestant could walk away with up to $25,000 in cash!

Live Music & High Energy Vibes

The party starts before the games begin! Enjoy upbeat music that sets the tone for a night full of excitement, laughter, and non-stop fun.

BBQ & Good Eats

Fuel up with mouthwatering BBQ and tasty snacks available on-site. Because great games deserve great food.

Group Hospitality Welcome

Planning a night out with friends, coworkers, or a celebration? Win Big Live is perfect for group outings—with reserved seating options and a shared experience like no other.

Grab Your Tickets Today — Before They’re Gone!

Whether you’re coming to watch, vote, or compete, there’s fun (and cash!) waiting for you.

Tier 1 – $50 + tax

Perfect for those who want to enjoy the full show experience from the audience.

  • General admission seating

  • Participate in live voting during most games

  • Enjoy the energy, cheer on players, and be part of the action

**Limited Availability

Tier 2 – $75 + tax

For those who want a shot at the spotlight and a little extra excitement.

  • All Tier 1 benefits

  • Eligible to be randomly selected to play live on stage

  • Vote in an exclusive bonus game just for Tier 2 ticket holders

**Limited Availability

Our Masterplan

Explore Thousands Of Digital Art And Collectibles.

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Our Vision

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Our Mission

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Our Value

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How It Works?

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Be Part of the Show

Vote live, cheer loud, and you might get picked to play on stage!

Play Skill-Based Games

Each game is fast-paced, fun, and based on skill—not chance. From trivia and mini-challenges to surprise rounds, it’s all about quick thinking, bold moves, and big laughs.

New Every Month

No two shows are the same! Every month brings brand-new games, fresh contestants, and exciting twists—so there’s always a new reason to come back and play.

Meet our team

Teamwork makes the dream work.

Henry Nicholson

Founder

Henry Nicholson

Founder

Henry Nicholson

Founder

Henry Nicholson

Founder

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Win Big Live Happens on the First Saturday of Each Month

Win Big Live Happens on the First Saturday of Each Month

Show-1

Morning Session

Show-2

Afternoon Session

Show-3

Evening Session

Why Attend Win Big Live?

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Win Big

Compete for up to $5,000 each month—plus a shot at $25,000 in our annual SUPER show!

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Get Involved

Vote live, cheer loud, and you might even get called on stage to play!

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Perfect Night Out

Great for dates, friends, or groups—fun, fast-paced, and unforgettable.

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Easy to Reach

Located in Oak Park, just minutes from downtown Chicago.

Common Question.

Most Popular Questions

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Maecenas porta eleifend pretium interdum commodo orci elit morbi semper. Inceptos cubilia primis quis pellentesque a vulputate ultricies est. Lorem dis praesent porta tincidunt nam urna felis tempus tellus dapibus nisi.

Maecenas porta eleifend pretium interdum commodo orci elit morbi semper. Inceptos cubilia primis quis pellentesque a vulputate ultricies est. Lorem dis praesent porta tincidunt nam urna felis tempus tellus dapibus nisi.

Maecenas porta eleifend pretium interdum commodo orci elit morbi semper. Inceptos cubilia primis quis pellentesque a vulputate ultricies est. Lorem dis praesent porta tincidunt nam urna felis tempus tellus dapibus nisi.

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