If you want to eat Italian food in Chicago, you can have it pretty much any way you want. There are expensive tasting menus, there is takeout pizza, and there are plenty of options in between. But it can be hard to find the best of those in-between spots, which is exactly why we made this guide. These are the places perfect for grabbing dinner during the week or having a date night without blowing a ton of money. When you want to eat a lot of pasta and share some reasonably priced bottles of wine, this list will help.
Head to Bar Roma in Andersonville for great rustic Italian food in a space that has a lot of wood and distressed furniture. They even make sure to leave bags of flour lying around, just to remind you they make all their pastas (like the fantastic cacio e pepe) in house. There’s an entire section of the menu dedicated to polpette (“the balls”), including variations made from spicy pork belly and veal. But we like coming here for the pastas specifically - you can’t go wrong ordering the day’s special.
Sono Wood Fired is a great utility player in Old Town. It has solid antipasti plus great pizzas and pastas, and it’s almost never so busy that you can’t get a table right away. Come here with a group, before a show at Second City, or on a date with someone who really can’t choose between pizza and pasta.
Most places in the Gold Coast are either high-end or ultra-casual. When you want something more mid-range, try La Storia. There are still white tablecloths, but the great Italian food is reasonably priced - particularly the excellent housemade pastas. As a bonus, they rival Piccolo Sogno with their amount of outdoor twinkly lights, so the large patio is a perfect place for a date.
This the sister restaurant to Siena Tavern that lives in a cooler neighborhood and doesn’t take itself as seriously. It’s loud and full of people, with a huge bar dominating the first floor and a larger dining area upstairs that’s perfect for groups. It combines a cool crowd with easy, something-for-everyone food. Pastas and wood-fired pizzas make up most of the menu, and they’re all worth trying - the prosciutto and fig pizza has a perfect balance of sweet and savory, and the gnocchi is pillowy and delicious.
You need a neighborhood spot that serves giant plates of pasta, and veal scallopini the size of the tablecloth. (Almost.) La Scarola can be that place. It’s as versatile as they come - ideal for a casual date night, weekly dinner with friends, or all-out Italian feast. As we said, the portions are huge, so either come here with a rugby team or expect leftovers.
In the midst of all the sports bars on Wells St. in Old Town is a great Italian restaurant. Topo Gigio feels exactly like the trattoria around the corner from your homestay in Florence - the one you strolled into drunk six days a week while giving America a bad name. It’s perfect for any occasion.
Orso’s is also in Old Town, and we like it for a lot of the same reasons we like Topo Gigio - it’s casual and comfortable, with plenty of easy Italian-American options like spaghetti with meatballs and chicken vesuvio. But the main reason we go to Orso’s is its outdoor patio, which makes us feel like we’re in The Secret Garden. That said, it’s a solid choice all year.
You can’t take two steps down Restaurant Row without coming across a trendy, just-opened place, or running into a former Top Chef contestant. But not every meal you have in the West Loop needs to be someplace with a sushi conveyor belt. Head to Viaggio when you want to keep it simple with a neighborhood institution. It’s been around for almost 10 years now, and its classic Italian food is exactly what you want it to be - tasty and comforting.
You’re getting together with a big group of friends. Tiffany wants to do something fun, Brian doesn’t want to spend too much money, and Allison is so picky she doesn’t really eat anything besides pizza, which is actually rather impressive. Make your reservation at Quartino and everyone will be satisfied. The two-story, small plates Italian restaurant in River North has easily shareable pastas, vegetables, and, yes, pizza. You’re welcome, Allison.
Nando Milano is the kind of place that can easily turn into your go-to neighborhood restaurant if you live in West Town. Even though it’s on the smaller side, it never feels too crowded. Plus, it has outdoor seating, and the housemade pastas and focaccia are delicious. Classic Italian dishes make up the majority of the menu, but keep an eye out for the seasonal specials, which are always worth ordering. In other words, you can pretty much forget about going anywhere else again, ever. Until they ask you to leave.
Sometimes (a lot of times) we want a place where we can knock back too much house wine and go face first into a pile of pasta and meatballs. In Lincoln Park, that place is Pasta Palazzo. The food is simple, fresh, and inexpensive. Most pastas cost around $10, and adding a protein won’t be more than a few extra bucks. We like it more for a casual midweek dinner than date night, but if this is date number 2,829 and you just want something quick, it’ll work.
The scenes-from-Italy paintings on the walls won’t trick you into thinking you’ve left Chicago, but that’s fine. A meal at Bella Notte will still probably take your mind off the fact that you just sat right in a wet spot on the El. Go heavy on the pastas (like the cavatelli or the lobster fra diavolo), and get half-orders so you can try as many as possible - trust us, you’re going to want to do that. Then take a cab home.
Looking for an Italian restaurant on Taylor Street is like looking for a steakhouse in River North - it’s not hard. And most of them are fine. But our pick is Davanti Enoteca, a small, always crowded place that’s great for date night or catching up with a couple friends. Cacio e pepe and polenta with the ragu of the day are staple orders. You won’t even realize that this is technically a chain restaurant (they have locations in San Diego, too).
The small neighborhood place in Lincoln Park where you go for a bowl of simple pasta and a glass of wine for no more than $25. And it’s been that way for 20 years. Their signature dish is the farfalle pollo with grilled chicken, tomatoes, mushrooms, and an excellent cream sauce, but any of the pastas will do the trick. You can’t beat it for the price.
We’ve long been huge fans of Riccardo Trattoria, a nicer Italian restaurant in Lincoln Park. But across the street is Riccardo Enoteca, the more casual place from the same owners. The focus here is on simple 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, so keep your dinner crew to a maximum of four. If you have more, draw straws to find out who has to leave and go to Trattoria. Sorry, those are the rules.
Tufano’s has no menus and a steady stream of regulars, so you may wonder if you’ve walked into a restaurant or accidentally crashed someone’s family reunion. And the answer is you’ve probably done both. Not much has changed here since 1930, and people still pour in for both the neighborhood atmosphere and signature dishes like their stuffed shells or sausage and peppers. There’s no shame in being a newbie, though. Check it out.