Where to eat Italian in Chicago when you’re not willing to settle.Less
Monteverde is at the top of this list for one reason: it’s our favorite Italian restaurant in Chicago. Every dish here is fantastic, from the housemade pastas like cacio e pepe and tortelli di zucca, to the ragu alla Napoletana (with perfectly-cooked pork shank, sausage, meatballs, and fusilli) - which is one of the most delicious plates of food we’ve ever eaten. Come here on a date, come here with a group, or come here by yourself and order every single pasta on the menu.
If you’ve eaten at Bavette’s or Gilt, you know they treat pasta with the honor and respect it deserves. Ciccio Mio in River North is an Italian spot from the same team, and the old-timey space looks like it could be a room in the mansion from Clue. The menu has antipasti, pasta, and mains, and everything from the lasagna with bolognese to the crispy chicken parmesan is delicious.
The food at this casual Italian restaurant in Humboldt Park stands out in Chicago’s pasta and chicken parmesan landscape, because every dish has some kind of creative twist. The meatballs are filled with melted scamorza, offering the benefits of a Juicy Lucy without the risk of third-degree burns. The deconstructed lasagna is a pile of handmade garlic mafaldine, whipped ricotta, and a mushroom bolognese that would win in a steel cage death match against any meat version.
This Italian steakhouse on the edge of Fulton Market is working hard at channeling mid-century-era glamour, complete with bartenders in waistcoats and a checkered marble floor. This place is loud and sceney, but it's also fun and the theme works. There are excellent steaks on the menu, but there is also perfectly al dente housemade pasta, and entrees like chicken parmesan and branzino that (almost) outshine the steaks.
A Tavola in Ukrainian Village is easy to miss because it looks like a regular ol’ house. But just beyond the foyer (because it is, in fact, an old house) is an intimate Italian restaurant, decked out with thick window curtains and black and white photos. It's full of regulars who’ve been eating there for years, and don't be surprised if you see a kid blowing out birthday candles. And in the summer, you can enjoy pillowy housemade gnocchi or short rib risotto on the secluded back patio.
This West Loop Italian spot is from the same chef as Boka, which means the food is great. And while the menu isn’t going to blow your mind with creativity it is delicious. The cacio e pepe ricotta dumplings are now our reigning definition of “decadent.” The pizza has a chewy crust, and the chicken parmesan stays crispy even while sitting in a rich tomato sauce. Reservations are few and far between, so plan on booking a month or so in advance, or snagging a seat at the bar right when they open.
Riccardo Trattoria in Lincoln Park is nice enough for a special occasion but doesn’t feel formal or stuffy. Order any of the pastas (the pappardelle with bolognese is delicious) and an entree like the osso bucco. This also happens to be one of the only restaurants with burrata that’s worth going out of your way for. It’s straightforward with just olive oil and prosciutto, but absolutely delicious.
Look, it’s not our fault that a restaurant owned by former E! Reality stars has some of the best Italian food in the city. RPM Italian is the kind of spot that Chicago does really, really well. It has big booths that can fit eight of your closest friends, an absurd amount of space, and feels like a 2009 episode of Gossip Girl, along with great service and a lot of delicious food. In fact, this spot’s bucatini pomodoro and the cavatelli are two of our all-time favorite pastas.
Enoteca Roma is a small spot in Wicker Park that you might not know 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 the penne arrabbiata or one of the handmade specials. And in the summer, the space becomes deceptively large thanks to a huge secluded back patio.
Just because a spot has a bar with regulars doesn’t make it “just like Cheers,” and saying so is usually wishful thinking and obnoxious. But Mart Antony’s might actually qualify. It’s an out-of-the-way spot on the border of West Town and the West Loop and looks like a typical neighborhood corner tavern. But, it’s also a fantastic Italian restaurant. The owner, servers, and bartenders are all warm and welcoming. Get the clams for an appetizer, and the braciole or lasagna.