If you want to eat Italian food in Chicago, you can have it pretty much any way you want. You can get an expensive tasting menu, you can get great Neapolitan pizza, and you can have pretty much everything in between. But it’s that in-between that can be trickier to find. These aren’t the restaurants where your pasta will be topped with truffles, but instead the places you can grab dinner during the week or take a casual date on the weekend without blowing a ton of money.
Expect lots of pasta, red sauce, and cheap bottles of red wine ahead. This is the casual Italian restaurant guide.
Hopefully you have a favorite neighborhood Italian spot that’s dark, cozy, serves giant plates of pasta, and makes you happy. And if you don’t have one, know that La Scarola is that place for us. It’s as versatile as they come, ideal for a casual date night, weekly dinner with friends, or all-out Italian family style feast. We also imagine it as the place we’d sit with Tony Soprano and discuss who gets whacked. Whatever the occasion, it’s casual Italian done right.
The other casual Italian restaurant in Old Town? Orso. It has many of the same characteristics we like about Topo Gigio - casual, comfortable, and plenty of easy Italian-American food options like spaghetti with meatballs and chicken vesuvio. But the reason we usually go with Orso is when we want an outdoor patio in this part of town. That said, it’s acceptable all year.
You can’t take two steps down Randolph or Madison without some new concept or trendy space. But not every meal you have in the West Loop needs to be from a past or future Top Chef contestant. So head to Viaggio when you want to keep it simple for an Italian dinner in the West Loop. It’s comfort food at its best.
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 most visited restaurant. And that’s particularly true if you live in West Town. It’s on the smaller side, which makes it ideal for an easy date night, or at least a double date if you’ve reached the point in life where that’s considered a wild night out. The classics are good, but keep an eye on the specials, which are always different and interesting.
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. That place in Lincoln Park is Pasta Palazzo. The food is simple, fresh, and inexpensive. Most pastas will ring in around $10, and adding a protein won’t be more than a few extra bucks.
In the midst of all the sports bars on Wells St. in Old Town are two good, casual Italian restaurants. 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 literally any occasion.
A typical Italian restaurant that’s been around for a while. But if you’re looking for a typical Italian restaurant in Bridgeport, this is the only smart choice.
“We’re looking for a cute little Italian restaurant that isn’t too pricey but has good food. And it needs to be north of Wrigley Field.” Great - you just described Anteprima. Or, we described Anteprima, but the next time you ask that question, know that you’re looking for Anteprima. It’s as cute and casual as you would expect any Andersonville restaurant to be, which means peak cuteness.
Are you in Italy? Nah, that’s just a giant painting of Venice on the wall and another one of some good-looking Italian sculpture dude that’s not the David. Either way, you’re as comfortable in Bella Notte as you would be sitting on a quiet street in Italy. Go heavy on the pasta specials and consider getting half-orders so you can try a few different kinds.
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 all fine. But our choice is Davanti Enoteca, a cozy, always crowded place that’s great for date night or catching up with a couple friends. Cacio pepe and polenta with the ragu of the day are staple orders. And if you have a bigger group, consider their River North location that serves the same great food but with more space (but, FYI, less charm.)
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 proponents 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. It’s a much more laid-back atmosphere here than across the street, with a focus on simple antipasti, pastas, and pizzas. Both restaurants are excellent choices, but if you’re looking for casual this is the move. It’s small and usually crowded, so keep your dinner crew to a maximum of four.
With no sign on the door and a solid stream of regulars, 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 at Tufano’s since 1930, and the people (many of them likely the same) are still pouring in for both the atmosphere and the food. Everybody’s welcome, though, so don’t be afraid to show your face.
There are a few Francesca’s around these days, but Mia Francesca’s in Lakeview is our choice of the bunch. You’ll never be mad about a decision to eat here, and anyone that’s mad about eating here with you probably wasn’t loved as a child.