Ever wonder if ChatGPT could create the perfect road trip itinerary?

Watch host, James Anthony III, take on The Hertz Challenge as he drives off on an AI road trip adventure in the Windy City of Chicago, Illinois! Behind the wheel of a limited-edition Hertz Shelby Mustang rental, he is ready to take on the day … with ChatGPT as his copilot.
 

First stop. Pizza for breakfast?

That’s a ‘yes’ from AI as James pulls up to Lou Malnati’s, known for Chicago-style deep dish pizza. With the place to himself, James realizes that pizza in the morning is quite delicious.

Walk it off.

AI knows how to plan with a much-needed walk after a big meal. James heads down the road for an architectural tour at the Oak Park Historic District, home of American architect Frank Lloyd Wright.

Ride a giant swan.

If walking off that pizza wasn’t enough, ChatGPT takes James to Humboldt Park to cruise the lagoon on a giant Swan boat … powered by pedaling. It was leg day for James.

Indulge in comfort food.

Back in the car – and hungry – AI’s itinerary takes James to The Chicago Diner for some comfort food, vegan style. Meat-free since ’83, this diner delivered some tasty BBQ wings, fries and a banana milkshake for dessert.

Beach.

Time to rev the Hertz Shelby Mustang engine and head to North Avenue Beach for a scenic stroll and a skyline view. With a sandy beach on Lake Michigan and spectacular views of Chicago, it’s the perfect place to take in the moment and relax. Or you could be like James and play volleyball.

Eat more pizza.

It’s dinner time and AI says you’re hungry … for pizza again? Chicago-style deep dish pizza originated in the 1940s, and it’s a big deal in the Windy City. There are many pizzerias that say they make it best, so James hit the road to Gino’s East for a taste test.

Have a laugh.

It just so happens that this Gino’s East River North Chicago location also features The Comedy Bar. Our favorite stand-up comedian and Hertz host, James Anthony III, takes the stage and closes the evening with some hearty laughs. Who knew that using ChatGPT to map out your road trip could be so much fun.

Get to your next Let’s Go moment in a Hertz rental car today.