PIZZA IS the quintessential food that comes in a myriad of shapes, sizes and flavor combinations. No matter what your preferences, pizza can be made the way you like it.
We’ve eaten greasy drunk pizza, chain pizza, New York style pizza, brick-oven pizza and frozen pizza. We all know the intangible difference between good pizza and bad pizza; but more than anything, we all know when we’ve tasted GREAT pizza.
Chicago transplant Robert Pickens came to Savannah about five years ago and immediately detected a deficit in the food scene.
“When I got here, I noticed there was no Chicago food and Deep Dish pizza was nonexistent,” Pickens says.

Pickens immediately found his niche in Savannah and dedicated the last four years to perfecting his epic Deep Dish Pizza Pie. As of March 2016, Pickens became the owner, chef, and delivery boy of Windy City Savannah, discreetly located inside Barrelhouse South on West Congress Street.
Pickens explains that the reason why so many people may not know about his pizza is that he’s “kept it underground.” He likes that people stumble on it through word of mouth.
Prior to his move to Savannah, Pickens was an admission and financial aide advisor for a local college in Chicago. While he does not have a formal culinary background, he comes from a Lithuanian family that enjoys cooking and he has a true passion for disseminating Chicagoan food to Savannahians.
Shortly after his military brother had been involved in combat and had experienced the horrors of war while deployed, Pickens chose to move to Savannah on his journey of “self reflection.”
His original intent was to buy a food truck, which was “impossible to do at that time.”
In the meantime, Pickens developed his Deep Dish Pizza Pie. The irony is that this is not a family recipe passed down from generation to generation. In fact, when he goes home, Pickens’ mother asks him to make his Deep Dish pizza for her.
“Honestly, the recipe was a lot of screwing around in the kitchen, involving a lot of trial and error. I made a lot of explicit pizzas, but my goal was to not make an Uno’s pizza. I thought, ‘How can I make my own pie the way I remember it when I was a kid?’ ”
Pickens aimed to make his version of pizza bigger and deeper than those found in Chicago. “I wanted to make a pie that is different from anything you have ever tasted.”
So what makes Pickens’ Deep Dish Pies so extraordinary? Each 10-inch round pie is 2 ½ inches deep, layered first with house made dough, then 2.5 pounds of mozzarella, followed by fresh toppings and finished off with scratch-made tomato sauce.
While Chicago Deep Dishes are typically made with butter crust, Pickens chose his own unique recipe that is crispy and airy without the extra grease and fat.
Because Pickens’ dough takes 48 hours to rise, customers must pre-order a few days in advance for dine-in or take ‘n’ bake.
Pickens utilizes Facebook as a way for patrons to place orders. Customers must first “friend” Windy City Savannah and then message or email Pickens with the date of pickup, round size and toppings.
If patrons choose the take ‘n’ bake route, Pickens will send them home with the pie in a springform pan and instructions.
While Deep Dish pizzas are conventionally made in cast iron skillets, Pickens found it was easier for customers to remove the pizza from springform pans, classically used for cheesecakes.
While he doesn’t always get his springform pans back, Pickens counts it as joy that he is able to share his food with the people of Savannah.
Whether you choose to dine-in or take and bake, Pickens will tag your name with a picture of your pizza on Facebook that says something along the lines of, “Your 8 inch round supreme Chicago-style deep dish is prepped and headed to the oven”.
If you choose to dine-in, Pickens will serve your pizza pie piping hot from the small rectangular window in the back of the Barrelhouse bar.
While Pickens has made some unconventional adaptations to the classic Chicago Deep Dish, there are two things he refuses to compromise on. First, he will not allow customers to take a baked pie home; they must eat it on site.
“The crust is supposed to be a certain way and there is a lot of room for error when they are driving home,” he says.
Pickens wants his pizza eaten fresh out of the oven.
Secondly, “I refuse to do slices, as my pies are too thick. When you cut into my pies, the cheese runs like lava.”
His answer to patrons wanting just a slice of his pizza is 6-inch round personal pan pies. The good news is, those are available any time Windy City’s doors are open and do not need to be pre-ordered.
Pickens is big on maintaining the high standards of his food. He brags that he has made everything on the pizza. If you order sausage, you can be assured he made the sausage. He also guarantees that the pizza dough was prepared with your pizza in mind.
My husband and I chose the dine-in option and were served the Supreme 10-inch round. Sure enough, I received my Facebook notification that my pizza was going into the oven.
When we got there we were served a pie like one I have never seen before. It had a thick and golden exterior with a deep red top layer. When Pickens cut into it, we could clearly see the layers that made this pizza so distinct.
First, the tender crust tasted like freshly baked bread and was able to withstand several pounds of cheese, toppings and sauce, without becoming soggy. There was a balanced ratio of crust to toppings, which seemed like a feat in itself.
The 2.5 pounds of mozzarella tasted fresh and sumptuous. The amount of gooey melted cheese in this pie is what pizza lovers dream about. Freshly cut peppers, pepperoni, onion and mushrooms were layered on top of the cheese, adding a garden-fresh zest.
This was all topped with Pickens’ homemade chunky tomato sauce that takes 3 ½ hours to prepare. This sauce was thick, rather than thin and runny, and seemed to float on the clouds of mozzarella.
This is the type of pizza where you can truly taste all the ingredients as separately as you see them in the pie, but come together in harmony with each bite.
While Chicago Deep Dish Pizza is the main attraction, Pickens serves a variety of other Chicago specialties like Italian Beef sandwiches, Pizza Puffs and Chicago Dogs (just don’t ask for ketchup, as this is a huge no-no in Chicago).
As far as his food truck is concerned, Pickens says it is “a work in progress.”
Pickens participated in Savannah Food Truck Festival in October, but not without a few setbacks.
“When we got there everything went wrong all at once.” Even though Pickens had to start a few hours late, his tenacity allowed him to work out the kinks, laugh it off and recover. “It was my initiation.”
While he did not serve Deep Dish pizza, the event was ultimately a success and people enjoyed his other Chicago classics. His main goal now is to figure out how to make personal Deep Dish pizzas on the truck.
Pickens is at a turning point. He has chosen to leave his day job to focus solely on Windy City Savannah. This difficult decision did not come without deliberation.
Pickens has found it difficult to work a full-time job and then open Windy City on weeknights and weekends, often staying until 5 a.m. Pickens aims to have Windy City open daily, as well as his truck operational by February 2017.
Check out the menu at windycitysavannah.com/
This article appears in Dec 14-20, 2016.


I’ve been friends with Rob for years and his brother as well and when he said he was going to bring Chicago-style deep dish to Savannah I was a huge supporter having been lucky enough to try them at home beforehand. I haven’t met a single person yet who’s been introduced to his deep dish, or any of his Chicago street food menu, that hasn’t instantly been impressed. In less than a years time, he’s added a food truck with the success and partnership with Barrelhouse South and they sky is the limit. You owe it yourself to not take my word for it but to try it for yourself because its a worthy experience.
-Marc Headley
With me being from Chicago, I can back up the taste, flavors, and the drooling that comes with “our specialties”. His pie and his Italian beef sandwiches are spot on. Thanks Rob!!
I had my 1st pie from Rob over the summer via my roommate and word of mouth from a few friends, needless to say I was not disappointed- the days, the deep dish crust …everything was right! Rob has it down and brings a taste of the Midwest to Savannah.
I had my 2nd WCP pie 2 weeks ago while some friend from Athens, Georgia were in town. I walked over to talk to Rob about a late night pie, he hooked myself and the boys from the band Burns Like Fire who were playing next door at The Jinx up with a late night last minute Supreme Deep Dish pie! The Boys were blown away!
If your looking for something different or not normally found in the South, get yourself a deep dish pie from Windy City Pizza – you won’t be disappointed!
I have had the great pleasure of sharing a kitchen with Rob on several occasions and I can tell you his secret ingredient. Love. This man loves what he does and it shows in the food. He is dedicated to his craft and has it down to a science, which enables him to yield the same amazing result in each and every pie. You would be doing yourself a disservice if you don’t try the best pie in town.
I’ve known Robert for a little over a year and he’s a class act – not to mention a phenomenal chef. Every time our band, The Norm, plays at Barrelhouse South, Robert makes sure we are fed and has something nasty for us to try. If you like deep dish pizza, hotdogs, and other staple food items from the Chicago area, then Windy City Savannah is a food experience you must have next time you are in Savannah!
Growing up in Chicago you have certain expectations when it comes to deep dish pizza. I was a little skeptical when I went with my brother and family. Robert knocked it out of the park (go Cubbies). Great crust, great taste, and some old styles to wash it down. The boys in Elmwood Park would be proud. Keep up the great work Robert. I will keep making the trek from Bluffton.
Being a Chicago Native, I have to say that if you haven’t had Windy City Savannah’s Chicago deep dish you are missing out. It’s probably the best Chicago style deep dish outside of the city itself. I’d put it up there with Gino’s East. All the ingredients are from Chicago and it brings a piece of home down to Savannah. Not only does is this deep dish spot on but the other Chicago foods are exactly what good Chicago food tastes like. Big thanks to Windy City Savannah for bring a piece of home down to Savannah. If you haven’t had it go get some…like RIGHT NOW!