Old Chicago Pizzeria – Naples

By | March 12, 2015


When you think of the best foods of Naples, Florida, certain items spring to mind. Most of them will revolve thematically around fresh, local ingredients and the best the sea has to offer. You think deep-fried Grouper sandwiches, steamed mussels, Chicago deep-dish pizza and handmade, fresh pastas covered in a white wine and garlic reduction.

Errrrr. Whoa. Pump the breaks. Does anyone else have the “One of these things is not like the other” song from Sesame Street playing in their head? Deep-dish pizza on the Gulf Coast of Florida. So strange. So true. So delicious.

During our previous four years, California Pizza Kitchen has been the staple of our pizza-on-the-beach dinner. Let’s face it, CPK is pretty awesome and somehow the location 1000 miles away in Florida is more accessible than the one at Ross Park Mall. I didn’t make the rules. I just follow them. Even the best traditions need a change from time to time, so we decided to work off-script and seek out a new pizza-on-the-beach pizza.

As you might suspect, the options are not fantastic. Places had weird hours, horrible reviews or both. What about this place? Old Chicago Pizza. Never heard of it and, even though it is on the main drag of Tamiami Trail in Naples, I cant remember even seeing it before. What do they have? Pretty standard fare overall. Scrolling through the menu for the first time there wasnt much that jumped out until – wait for it – deep dish. Deep dish that, according to the menu is “True, traditional deep dish, brushed with butter and our roasted garlic, olive oil, topped with sauce, pomodoro, thick-sliced mozzarella and fresh herbs.” I was already sold at this point, but then I read on “Prepared from scratch. Allow 45 minutes bake time.” This was not a deterrent. Rather, it was a challenge. I could wait. I should wait. No! I must wait. Any pizza that is cooked in under 45 minutes can only be garbage compared to this authentic Chicago pie in the heart of Naples. Thirty minutes or less. Ha! I scoff at thee.

I ordered. I waited. I picked up. The place was empty upon my entrance but for two servers hanging by the register. The one with the gold tooth said something funny. I really can’t remember what it was, though. You know … because of the tooth.

I didn’t peak under the lid as I love to delay the reveal. I couldn’t smell it or taste it, either. The most surprising initial impression was the weight. I hear 10 inch pizza, I think light weight. This could not be farther from the case. Think gallon of milk rather than pizza. Somehow, the weight triggered a Pavlovian response. I may have dripped on the box.

Cut to peeling rubber. Rushing to the beach and what did I find?


Mind you, I’m not a religious man. Prior to this, I couldn’t tell you where I stood on the destiny versus free will debate. That all changed this day my friend. I was put on this planet to eat this pizza. And I did.

Pepperoni layered thick and huge hunks of sausage came along for the ride. Top to bottom, this was an amazing, solid pie. The description from the menu held true. The crust was soft, not chewy and well-flavored with butter and garlic without being greasy. The tomatoes were crazy good and perfectly seasoned while the cheese held in all together like the forgotten bass player from your favorite band.

A little sand from the blowing wind only added to the textural delight that was my deep dish from Old Chicago. I recommend getting a salad to-go as well. This pie needs to have a roughage buffer between slices in your stomach. We went with the bistro. Ditalini in a salad? Why not?

If you can manage more than two point five pieces in one sitting, you are more of a man than I. The good news is that this deep dish was as good the next day and even better the next making it well worth the $23. I would gladly pay it again.

Consume.Review.Repeat scores Old Chicago Pizzeria’s deep dish 8.5 distended stomachs out of 10.

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