CHIGuide
14 Excellent Old-School Italian Restaurants
photo credit: Susie Lacocque
When it comes to Italian food, Chicago has everything. But when you’re looking for something classic—a neighborhood place with friendly service and huge portions of meat, cheese, and carbohydrates covered in red sauce—here are the spots to try. Not all the places on this list are technically old old, but they all have old-school Italian style.
THE SPOTS
photo credit: La Scarola
Ask a random person in Chicago to name a classic Italian restaurant, and there’s a good chance they’ll say La Scarola. It’s a neighborhood spot with white tablecloths, old photos of celebrities on the wall, giant plates of pasta, and veal scallopini that’s the size of a mattress. This place is ideal for a casual date night, weekly dinner with friends, or all-out Italian feast. Put it at the top of your old-school bucket list.
If you’ve never eaten at Enoteca Roma, that needs to change immediately. It’s a small, quiet spot in Wicker Park that serves fantastic Italian pastas and bruschetta. Start out with a bruschetta flight (you can choose five different types for $12) and a polenta board for the table (our favorite is topped with a venison bolognese). Then round things out with a pasta, like the penne arrabiata or one of the handmade specials. If you can move after eating all of that, head next door to the Empty Bottle for a show.
The West Loop isn’t known for having an abundance of quiet, old-school spots. In fact, nowadays most of Restaurant Row is full of trendy new places, fast-casual chain restaurants, and the McDonalds that takes up half a block. Head to Viaggio when you want to keep it simple with a neighborhood institution. It’s been around for more than 10 years (which is about 50 in West Loop years), and the food is exactly what you want it to be: tasty and comforting. Get the meatball salad. Yes, you read that correctly.
Riccardo Trattoria is nice enough for a special occasion, but also affordable enough that your little brother can take your parents there to thank them for letting him move back home to work on his screenplay. Order any of the pastas (the pappardelle with ragu is delicious), and an entree like the osso bucco. This also happens to be one of the only restaurants on this list with a burrata dish worth going out of your way for. It’s straightforward (with just olive oil and carpaccio), but magically delicious. Like Lucky Charms, but with meat and cheese.
Just across the street from Riccardo Trattoria is Riccardo Enoteca, the more casual place from the same owners. The focus here is on antipasti, pastas, and pizzas. Both restaurants are excellent choices, but if you’re looking for a low-key meal, this is the place. It’s small and usually crowded, and a good choice if you happen to have small children with you. If you happen to not like eating around small children, go to Riccardo.
photo credit: Christina Slaton
Tufano’s has no menus (everything is just on a chalkboard), and it’s full of regulars, so you may be concerned you’ve stumbled into someone’s family get-together instead of a restaurant. Honestly, since everyone seems to know each other, you’ve probably done both. Not much seems to have changed here since 1930, and people still come for the neighborhood atmosphere, plus signature dishes like the stuffed shells or sausage and peppers. And unlike your judgmental family members, everyone here is very nice, whether they know you already or not.
photo credit: Mart Anthony
Mart Anthony’s is an out-of-the-way spot on the border of West Town and the West Loop. It looks like a typical neighborhood corner bar, because, well, it is. But it also happens to be a pretty great Italian restaurant. On any given night it’s full of friends getting together after work, and couples on casual dates. The servers and bartenders are warm and welcoming, and will chat with you even if you’re not a regular. Get the braciole or the lasagna, both of which will have you covered in the leftover department for about three days. All the sauces here are very flavorful, and the housemade sausage is particularly good.
photo credit: Derrick Koch
This Lincoln Park Italian restaurant is popular for a reason—it has great pastas and attentive service. The three dining rooms (on two levels) are always really busy, so you should definitely make a reservation. The bread here is delicious, and so are all the sauces - order the bolognese with housemade rigatoni, or go with their gnocchi in a pesto sauce.
photo credit: Susie Lacocque
Club Lucky opened in the early 1990s, and it’s meant to resemble an old 1940s Italian supper club. It’s loud and crowded and the main dining room is huge, with lots of tables and big leather booths. Come here with a group, and prepare to float away on a sea of martinis and red sauce. Order the fantastic handmade cavatelli in vodka sauce, and you can’t go wrong with the lightly fried calamari as an appetizer. Most of the dishes here are meant to serve two, so we mean it when we say you should come here with friends.
photo credit: Sandy Noto
Like a bonus level in a video game, there’s a pocket neighborhood inside Pilsen called the Heart Of Italy. It’s just one street with a number of old-school Italian restaurants, and food-wise, Ignotz is the best. The chicken parmigiana is worth traveling for, and the lasagna is really good, too. Not to mention that they win the award for best table bread setup, since it comes with a roasted bulb of garlic for spreading, plus some breadsticks you’ll only wish were unlimited. The whole restaurant is in a refurbished house, and you’ll be eating in a living room complete with a fireplace, and family photos on the mantel.
photo credit: Sandy Noto
Topo Gigio is a family-friendly spot surrounded by sports bars in Old Town, and it’s perfect for any occasion when groups want to share bottles of wine and giant plates of pasta. There’s also a nice seafood selection (including a very good spaghetti with clams, calamari, mussels, and scallops). And a great patio you can hang out on during the summer.
This casual Italian restaurant in Little Italy is from the owners of Tempesta, one of our favorite sandwich and specialty shops in the city. Peanut Park’s menu has a variety of antipasta (the housemade focaccia with ‘nduja is wonderful), pastas, and mains like a crispy chicken parmesan that's covered by a blanket of cheese. It also has a large bar and very friendly service, which are two things that make it a great destination for post-work pasta and wine.
Gene and Georgetti’s is technically a steakhouse—in fact, it’s Chicago’s oldest steakhouse, since it’s been around since 1944. But it was opened by two Italian guys, which means this is a great spot to get Italian food, too. It’s the type of place where you want nothing more than a big steak and an even bigger bowl of spaghetti and meatballs.
photo credit: Sandy Noto
We don’t say this lightly, but going to Bruna’s is like stepping into a time machine. It’s the second spot from the Heart Of Italy on this guide, and its atmosphere is the most aggressively old-school (which makes sense, since it opened in 1933). As with most classic spots, you walk through the bar area to get to the back dining room, which is decorated with murals and busts. There’s even a picture of “Bella Bruna” above the entryway. The Italian food is solid (the sausage and peppers are particularly good), and the pastas, while not housemade, are well-cooked and have flavorful sauces. Come here for the history, and to be grateful Prohibition ended (also in 1933).
