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Jason “Deep Dive” Lord • • About the Author
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The Windy City Whodunit – Powered by GPT

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The Windy City Whodunit – Powered by GPT

The Windy City Whodunit – Powered by GPT

Editorial cartoon showing Jason and Kellie exploring Chicago through an AI-powered scavenger hunt

What do you get when you blend a classic detective mystery, a tech-powered scavenger hunt, and two creative content creators roaming Chicago? You get a citywide whodunit powered by ChatGPT—and captured in a bold editorial cartoon style.

🔍 The Gameboard Is Chicago

Chicago isn’t just the backdrop—it’s the board. In this AI-guided scavenger hunt, every iconic location becomes an oversized tile in a living game. Jason and Kellie, decked out like noir-era sleuths, traverse the urban jungle solving whimsical clues like:

  • Decode the Jazz Club Clue 🎷
  • Ride the Riverwalk Route
  • Find the Ghost Tour Password
  • Solve the Deep Dish Cipher 🍕

The AI in Jason’s hand—our proprietary Scavenger Flow engine—lights up with suggestions and challenges in real-time, while Kellie’s backpack map (dubiously sourced from ChatGPT) leads them through puzzles and places only locals would know.

💨 The Clues Ride the Wind

In the background of the cartoon, the “Windy City” becomes a literal player, carrying QR-coded clues and sarcastic speech bubbles like:

  • “Midwest Mystery Meal”
  • “AI Suggested Stop: Secret Rooftop Bar?”
  • “Bonus Point if You Find Al Capone’s Toothpick”

Each clue is part fact, part fiction, and all fun—making the experience feel like a hybrid between Jeopardy, Clue, and Indiana Jones.

🎩 A Feline with Secrets

No Deep Dive AI adventure would be complete without our recurring mascot: the smug, chunky Russian Blue cat. In this scene, the cat wears a Sherlock Holmes cap, curled up in Kellie’s backpack side pocket and holding a mysterious clue card marked:

“Final Puzzle Piece – Don’t Tell Jason.”

Whether companion or saboteur, this little furball always seems to know more than he lets on.

🎙️ Vacation or Content Research?

As a sarcastic banner flaps overhead—“VACATION? NO, IT’S CONTENT RESEARCH!”—the line between work and play blurs completely. The cartoon pokes fun at the modern hustle: everything, even joy, becomes brand fodder.

Jason investigates riddles. Kellie records podcast snippets. The cat naps like he owns the trip. And the whole city becomes a sandbox for creators, sleuths, and AI-fueled explorers.

🧠 Powered by GPT, Inspired by Curiosity

All of this is made possible by our experimental AI app, Scavenger Flow. Using real-time data, neighborhood histories, trivia, and location-based logic, it builds an evolving scavenger experience that reshuffles itself depending on your choices.

This isn’t your average city tour. This is an interactive mystery where the final chapter is written by you… and maybe your cat.

🎧 Listen & Watch Our Deep Dive Episode

🧳 Gear Up for Your Own Mystery Hunt

Inspired to create your own AI scavenger experience? Here’s what helped us bring the cartoon to life—and power our Chicago adventure:

As an Amazon Associate, Deep Dive AI earns from qualifying purchases. Your clicks help fund our curious quests—thank you!

📣 Join the Hunt

Have ideas for the next AI-powered scavenger city? Should we turn this into a downloadable game or mobile app? Drop your theories, clue ideas, or snarky banner lines in the comments—or tag us on socials @DeepDiveAI.

And remember, the game isn’t over until the cat says so.

#DeepDiveAI #ScavengerFlow #ChicagoChallenge #EditorialCartoon #AITravel #ContentAdventure #WindyCityMystery

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