Roadtrips & Driving TipsTravel

Epic Taste-Testing Road Trip: Chicago Style Pizza vs. New York Style Pizza

Photo of author

By Joshua

Love food? Take a foodie road trip.

And if you like pizza… Take a pizza road trip!

You’ve heard the comparisons of Chicago pizza versus New York pizza before.

new-york-style-pizza Chicago style pizza!

Folks from the Windy City say their deep-dish pizza is better, while those in the Big Apple claim nothing trumps their thin, floppy pies.

So, if you’re up for a road trip, then hop in the car and taste for yourself who has the better pizza!


Planning A Pizza Road Trip

I don’t discriminate much when it comes to pizza, but I know a lot of people who do.

Some folks are gladly willing to take trips to New York City and Chicago just to taste-test different pizzas and make a decision as to which pizza pie reigns supreme.

Personally, I would ask why stop at only New York City or Chicago? I know Boston pizzas and Philadelphia pizzas are pretty tasty, too. Even my hometown of Tampa, Florida, is known for a type of Sicilian pizza pie known as scachatta.

But get too many pizza restaurants in one delicious post and my foodie head will be spinning faster than pizza dough being tossed in an old-fashioned pizzeria with red-and-white checkerboard tablecloths and swag-chained Tiffany lamps. Mamma mia!

Taking a road trip from Chicago to New York City — or vice versa — is no less than an 800-mile (one way) road trip that takes a solid full day of driving.

Live any farther than along the Interstate-80 corridor in the vicinity of Lake Erie and you’re probably talking about tackling a road trip that would take you a few days and a couple thousand miles (or more) to complete.

But if you’re game to wait more than 30 minutes to enjoy a pizza (and it won’t be free), then a pizza tasting road trip through New York City and Chicago is definitely the way to go!


New York Pizza Road Trip Tips

New York Chicago Pizza Trip

Whether you’re coming from the north, south, or west, you’ll know you’re about to enter New York City when you see its mammoth skyline rise above the horizon.

I can usually see the towering spires of the city’s buildings from more than 20 miles away on a clear day as I come up Interstate-95 from the south.

If you’re saving up money to buy a stack of pizza pies, then you’re probably best off staying outside the city. You can find great hotel rates in eastern New Jersey, which is a simple bus ride or taxi cab trip across the Hudson River from New York City.

Once you’re in the city, you’ll find pizzerias on every corner.

If you’re like Michael Scott, the boss from the NBC sitcom The Office, you might even find a few familiar pizza joints in New York City:

If Sbarro is also your favorite New York City pizza place, no worries — I think Sbarro is pretty tasty, too.

But when I’m in New York City, I try to find some local joints — the ones I can’t find in the malls back home in Florida.

Not all New York City pizzerias serve thin crust, floppy pizzas oozing with cheese. The array of pizza options in New York City range from thicker-crust Sicilian pizzas to gourmet pizzas covered in high-end toppings.

There’s also a fair share of pizza joints in New York City serving slices for less than $3 a pop.

Here are some of the best pizza places in New York City:


Chicago Pizza Road Trip Tips


The Windy City won’t enter a pizza taste-testing contest sitting down!

Like New York City, Chicago has a long and colorful pizza history, and you’ll find a delectable array of incredible places to grab a pie in Chi-town.

Chicago’s central location in the Upper Midwest means it’s easy for pizza lovers from all over the country to trek into the city for some amazing eats.

Also like New York, staying in Chicago is pretty expensive. So you might want to consider lodging somewhere outside Chicago and driving into the city to go about your pizza taste-testing tour.

Once in Chicagoland, ‘za foodies will find everything from crispy thin crust pies to massive, deep dish pizzas big enough to feed you and the rest of your neighborhood (quite literally, I’m sure).

Here’s a rundown on some of the pizza places you should check out when you’re in Chicago:



More Ideas For A New York/Chicago Road Trip