I met Jonathan Porter, the founder of Chicago Pizza Tours, last winter, and he was kind enough to not only share a ton of pizza-related advice and stories with me, but also to invite me out for a tour with my friend (and strong Chicago pizza opinion haver), Tim Giuffi of Lyman Ave. Bread.
Since the spring of 2010, Jonathan has been leading tours to some of Chicago’s most unique pizzerias like Pizano’s, Flo & Santos, Coalfire, Piece, Robert’s Pizza & Dough, Labriola, Bartoli’s, and once upon a time included stops at legendary Chicago pizza stalwarts Pequod’s Pizza and Italian Fiesta Pizzeria (which is famously just a carryout storefront, so they would loan Jonathan two folding chairs to set the pizza boxes on).
Tim and I trekked downtown early one Saturday last spring to eat way too much and learn about the history of pizza in Chicago.
I also had the chance to speak with Jonathan at length after the tour to get a lot of additional background into how he built up his relationships with those specific pizzerias, and why he thinks they’re noteworthy stops for people experiencing Chicago pizza for the very first time.
First stop!
We met up with the rest of our tour group — which including Tim and I consisted of 22 in total — at 11 a.m. outside the Pizano’s at 61 East Madison St., just across from Millennium Park.
Pizano’s was opened in 1991 by Rudy Malnati Jr., in part to honor the legacy of his father, Rudy Malnati Sr., who not only worked at the original Pizzeria Uno back in the 1940s, but is also often credited as being one of the main developers of deep dish as a style of pizza. Pizano’s uses many of Rudy Sr.’s original recipes, as well recipes from the matriarch of the Malnati family, Donna Marie. They have a menu packed with pasta and Italian specialties, as well as pizza in both deep dish and thin crust/tavern-style forms.
Pizano’s was the second restaurant to partner with Jonathan way back in 2009 when he was first putting together Chicago Pizza Tours, and after some wise (and pointed), advice from Rudy Jr., it’s been the starting location for every one of Jonathan’s original tours ever since:
“Pizano’s was the second or third place I called on. We wanted to have something that had great historical significance to the creation of the deep dish pizza, and it was owned at the time by Rudy Malnati Jr., who has since passed. I had dropped stuff at Pizano’s, and then Rudy called me and said, “Come in Tuesday at 10 a.m.” I came in and presented the whole thing to him, and I think I told him they would be my last stop. And he looked at me like I was an idiot, which I was at the time, and he’s like, “No. You’re gonna start here. It’s right across from Millennium Park, and the pizza is best right when it comes out, when it’s still piping hot.” So he basically sold me. And Rudy Malnati is a really intimidating figure. So I just said, yes sir, we’ll start here. I knew we’d figure out the rest of it. Then we had a handshake and we’re off and running. That changed the entire tone of what I thought the tour would be. I figured we’d have the big ending here, but instead it became a chance to front-load with all this historical deep dish information. And I think it worked out better that way. They’ve been our starting location for more than 14 years now, and the first words out of my mouth on any sort of official pizza tour took place inside of Pizano’s.”
Our tour guide, James, met us all out front, then led us inside and down into the basement of Pizano’s. Part of the experience on any kind of tour is the group itself, and we had a ton of Chicago pizza first timers, including people from as far away as Iceland, Poland, Utah, Nebraska, and Pittsburgh.
James gave us some general info about the tour before getting into specifics on the history of deep dish, as well as the role the Malnati family played in it. He also addressed some Chicago pizza misconceptions for those not fully indoctrinated yet, and while I’m not going to share a ton of the specifics from the tour (learning them is half the fun), I will share one of my favorite stats he dropped: Of the roughly 2500 pizzerias in the Chicagoland area only about ten percent of them serve deep dish.
Then it was pizza time:



As you can see we started with both deep dish and tavern-style. There was a thin cheese. A thin sausage (Jonathan makes it a point to always include sausage from Pizano’s since they use Anichini Brothers, one of Chicago’s best, and oldest, sausage manufacturers). A deep dish cheese, a deep dish sausage, and a Mark’s Special deep dish, which they also always make a point to include in case there’s vegetarians on the tour :
“The Mark’s Special is garlic, basil and sliced tomatoes. I love doing that for the tours, because I don’t know how many vegetarians I’ll have. They can tell us in the pre-buy section, but sometimes one person will buy tickets for eight people and might not realize three people in their group are vegetarian. It’s a super delicious, super light version of a deep dish pizza. So I love that as a starting point. And you don’t get too full off it.”
As for the pizza itself? If you’ve had Lou Malnati’s, Pizano’s is a more flavorful and crispier version. Tim and I both enjoyed it, but it wasn’t either of our favorite pizzas of the day:
CPN: What did you think of Pizano’s?
Tim: I liked it more than I thought I was going to. Both the tavern and the deep dish. And I think it’s because they were so fresh.
CPN: Did you have a preference between them?
Tim: I felt like the dough is pretty much the same for both, right?
CPN: It’s just that straight up Malnati’s butter crust.
Tim: At the end of the day I’m always going tavern over deep dish. Those two slices of deep dish I had today? That’s it for the year. I don’t need deep dish again for a year.
CPN: Which is exactly what James said. A couple times a year, and you’re probably taking somebody else when you do it.
After we finished eating it was time to catch our ride:
Chicago Pizza Tours uses a good, old regulation school bus for transport, so thankfully there’s plenty of space to stretch out so you don’t have to awkwardly jam yourself in next to another adult (especially after you’ve consumed a large quantity of pizza). Ms. Carolyn was our driver, and she was funny and fantastic.
Second stop!
Located in the South Loop, Flo & Santos is a warm, large, exposed brick and red-boothed pub and eatery, with a beautiful outdoor beer garden. The name of the restaurant is an homage to a real couple from the South Side of Chicago — Florence (Flo) was from Poland, and Santo was from Italy. Flo and Santo's dinner table always had the best of both Italian and Polish dishes, and the goal of the restaurant is, “to honor that heritage and all the Polish and Italian immigrants who made Chicago what it is today.”
Jonathan first included Flo & Santos as a tour stop in the spring of 2011, right around Chicago Pizza Tours’ one year company anniversary. The realtionship began partially because of a personal connection, but it also coincided with a huge jump in the popularity of the tours themselves:
“Flo & Santo’s weren’t there for the first year. Part of the reason why is they hadn’t opened yet. The second stop at that point was Italian Fiesta, which is down in Hyde Park. It’s the Obama’s favorite pizza, and it’s a nice, greasy, tavern-style. It was one of my favorite reveals on the tour for two reasons; one, we were down in Hyde Park and people were like, “Where the Hell are we?” We’d take them down Lake Shore Drive for like forty blocks. The second thing is, we’d pull over into this strip mall, and it wasn’t a bad neighborhood, but for some people they’d see us getting pizzas slid to us through bulletproof glass and maybe there’s a bit of a freak out and some excitement in that. They’d give us two folding chairs, and we’d put a pizza on each chair. And back then we had maybe eight or nine people, so we’d just crowd around because there was nowhere to sit. We were the only ones allowed to eat inside there. I still to this day miss bringing groups there, but it’s just not feasible now. Flo & Santo’s comes around in early 2011, and the guy who was the head chef when they originally opened was a fraternity brother of mine. He had reached out to me because they were doing pizza and he knew I was doing pizza tours and he asked me to come in and try it. So I was there on opening night and I learned a lesson, never try a restaurant on opening night. Don’t even go the first week, maybe even the first month. The crust was like a saltine cracker, and I don’t even mean it was crispy, it literally had the flavor of a saltine cracker. The cheese was kind of melted, and it was the whitest cheese ever, not what we expect on a tavern pizza where the cheese burns and spills over the edges a bit. Everything was just lackluster. I wasn’t going to be a jerk to my buddy, so I said I loved it and I’d come back. Then he asked about bringing a tour by and in the back of my head I was like, there’s no way I’m bringing a tour here. A month or two later he called me, and he’s kind of abrasive, and he goes, “What the Hell is going on?!? Get over here and try my pizza again!” So I went back and I was blown away. Thank God he fixed it, because I didn’t know what I was going to do to try and dance around the situation. It’s in the vein of Vito & Nick’s, but not quite the same. He had figured it all out, and fixed the pizza. That was around the end of our first year, and in that first year we ended up taking out somewhere around 800 people, so I thought we were off to a good start. But then in May 2011, our thirteenth month, we ended up taking out 500 people, so the growth was skyrocketing. Then our groups got bigger, and it brought us well over the limit of what we could bring to Italian Fiesta, so Flo & Santo’s just slid into that spot there in year two.”
Flo & Santo’s is a little over a mile from Pizano’s, so it was our shortest bus trip of the day, but that didn’t stop James from sharing a true Chicago deep cut with us along the way; if you had to guess which historically famous Chicagoan was responsible for the implementation of food expiration dates (born specifically from his fight to create “sell by” dates on cartons of milk), who would you think it was? You could have given me a thousand chances and I would never have guessed it was Al Capone.
I’d been to Flo & Santo’s a few times before, so I knew how good their pizza is, but I had yet to try what ended up being my favorite pizza of the entire day:


As you can see Flo & Santo’s only does tavern (though their menu also has plenty of sandwiches, entrees, and legit Polish food). For the tour they ordered us a cheese, a sausage, an Italian beef (beef, hot giardiniera, caramelized onion, and fire-roasted tomato), and the standout of the day, a Flo’s Polish pizza — which is topped with kielbasa, sauerkraut and applewood smoked bacon. It’s something really special.
“It’s the only place in the world that does a Polish pizza. Back in 2011 the TV show Chicago’s Best came down to taste their Polish food, and they ordered a couple pizzas. My buddy told them, “You know we do a Polish pizza too?” He said before that episode they did 20 Polish pizzas a week, but then after it aired they were doing 60 a day. Paulina Meat Market does all the sausage for them, so they had to call in and be like stop what you’re doing and make us as much Kielbasa as you can. Just one little segment on TV and now everyone and their brother is like, Polish pizza! And nowadays when I do it I don’t tell them what’s on the pizza until afterward. I used to tell them before and people were like, kraut?!? No. So I tried it without the sauerkraut to try and make everybody happy and because I still wanted them to try it, but it’s not right without it. It’s too salty, and too meaty, and there’s nothing to cut it. It needs that vinegar. So I went back to the original order and now I don’t tell them what’s on it until after they’ve eaten it.”
And it wasn’t just me. Of the four restaurants we visited that day the pizza disappeared at Flo & Santo’s the fastest. And they even (almost!) impressed Tim:
Tim: The kielbasa and sauerkraut pizza was the best pizza we had.
CPN: Does that count as a quality tavern-style for you? I know last time you said you hadn’t had quality tavern-style yet.
Tim: My square of the Italian beef pizza was from the middle. It wasn’t crispy, so it felt like just eating toppings. But the piece of the Polish pizza was crispy. I got some crust, so that was good. So it’s consistency.
CPN: My 8-year-old only prefers the middle, because he just wants all the cheese.
Tim: I’m down with that so long as it’s crispy. There has to be a way to do that, right? I can’t imagine as a pizza maker you’re happy with it if it’s not crispy.
CPN: I think that’s just the nature of that pizza, though.
Tim: I don’t know enough about it because I’ve never made it.
I love Flo & Santo’s as a restaurant. It’s a fantastic representation of everything you imagine a quintessential Chicago neighborhood tavern-style pizzeria to be and even though it started on the tour because of a friendship, that’s an essential part of the reason why Jonathan keeps bringing people back:
“Flo & Santo’s gives you the true feeling of what it’s like to be a local Chicagoan eating pizza. We don’t always run off to the deep dish place across from Millennium Park. I love Pizano’s for what it is, but that’s not everyday pizza. At Flo & Santo’s you’re getting a tavern pizza with tavern ingredients. The cheese is coming from Joliet, it’s not coming from some farm in Wisconsin. It burns a different way than that cheese burns, and that’s part of the nostalgia that goes with that thin crust. It’s the reality of pizza in Chicago.”
I’ll be back with the another post detailing the second half of the tour in a few weeks. Even though Flo & Santo’s was my favorite pizza of the day, the restaurant we went to next was my favorite stop of the tour for a reason you may not entirely expect.